NP-MRD: Showing NP-Card for Cynaroside (NP0043860)

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Record Information

Version

1.0

Created at

2021-06-22 17:26:15 UTC

Updated at

2021-08-20 00:00:45 UTC

NP-MRD ID

NP0043860

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cynaroside

Description

Luteolin 7-glucoside, also known as 7-glucoluteolin or cinaroside, belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Thus, luteolin 7-glucoside is considered to be a flavonoid. Luteolin 7-glucoside is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Cynaroside is found in Arrhenatherum elatius, Achillea biebersteinii, Achillea collina, Achillea fragrantissima, Achillea millefolium, Achillea pannonica, Achillea santolina, Acilepis saligna, Agastache foeniculum, Agrimonia eupatoria, Ailanthus altissima, Ajuga lupulina, Allium rotundum, Aloysia citrodora, Ammannia coccinea, Ammothamnus lehmannii, Anastatica hierochuntica, Angelica keiskei, Antennaria dioica, Anthemis auriculata, Aquilegia ecalcarata, Arnica acaulis, Arnica angustifolia, Arnica chamissonis, Arnica cordifolia, Arnica gracilis, Arnica longifolia, Arnica mollis, Arnica sororia, Artabotrys hexapetalus, Artemisia assoana, Artemisia caucasica, Artemisia palustris, Artemisia rupestris, Artemisia xerophytica, Arum maculatum, Asphodelus ramosus, Asteriscus graveolens, Asyneuma campanuloides, Bacopa monnieri, Bahiopsis deltoidea, Ballota acetabulosa, Ballota hirsuta, Bartsia alpina, Bidens frondosa, Bidens tripartita, Biebersteinia multifida, Biebersteinia orphanidis, Bischofia javanica, Brandisia hancei, Broussonetia papyrifera, Bryum argenteum, Rosulabryum capillare, Bryum pseudotriquetrum, Buddleja officinalis, Buphthalmum salicifolium, Campanula armena, Campanula lactiflora, Campanula ossetica, Campanula pendula, Campanula persicifolia, Canarium album, Capsella bursa-pastoris , Carallia brachiata, Carduus acanthoides, Carduus nutans, Carthamus lanatus, Caryopteris tangutica, Catalpa speciosa, Centaurea cyanus, Centaurea montana, Centaurea pseudoscabiosa, Cephalaria gigantea, Cephalotus follicularis, Chaerophyllum aureum, Chaerophyllum hirsutum, Chondrilla juncea, Chrozophora tinctoria, Glebionis coronaria, Chrysanthemum morifolium , Chrysanthemum zawadskii, Cirsium heterophyllum, Cirsium palustre, Clinopodium umbrosum, Codonopsis clematidea, Codonopsis foetens, Codonopsis lanceolata, Codonopsis ovata, Colchicum speciosum, Colocasia esculenta , Coreopsis basalis, Cornulaca monacantha, Cotoneaster multiflorus, Cotula cinerea, Crepidomanes minutum, Crotalaria verrucosa, Cuphea wrightii, Cyanthillium cinereum, Cyanthillium patulum, Carex fraseriana, Cynara cardunculus, Cynara cornigera, Cynomorium songaricum, Cytisus hirsutus, Daphne gnidium, Daphne oleoides, Dracocephalum multicaule, Dracocephalum nutans, Dracocephalum tanguticum, Echinop ritro, Elsholtzia ciliata, Elsholtzia rugulosa, Epimedium pubescens, Equisetum arvense, Eryngium campestre, Euphorbia humifusa, Euphorbia maculata, Ferula assa-foetida, Ferula varia, Frullania muscicola, Fuchsia colensoi, Fuchsia splendens, Galeopsis bifida, Galinsoga parviflora, Genista corsica, Genista lydia, Genista sessilifolia, Gentiana arisanensis, Gerbera jamesonii, Glechoma hederacea, Glycyrrhiza glabra, Gymnarrhena micrantha, Halenia corniculata, Halleria lucida, Helichrysum arenarium, Helichrysum stoechas, Heteromera fuscata, Hieracium gymnocephalum, Hieracium naegelianum, Humulus lupulus, Hyparrhenia hirta, Digitalis chalcantha, Itoa orientalis, Ixeridium laevigatum, Ixeris tamagawaensis, Jacaranda decurrens, Lactuca formosana, Lactuca quercina, Lactuca serriola, Lactuca viminea, Lagotis brevituba, Lamyropsis cynaroides, Launaea capitata, Launaea lanifera, Lavandula dentata, Lawsonia inermis, Leiothrix curvifolia, Lepidothamnus laxifolius, Leycesteria formosa, Libocedrus plumosa, Ligustrum vulgare, Limonium axillare, Linaria macroura, Linum grandiflorum, Lippia alba, Lippia graveolens, Lippia origanoides, Lippia sidoides, Lomatium dissectum, Lomelosia caucasica, Lonicera gracilipes, Lonicera japonica, Lotus uliginosus, Luetkea pectinata, Lupinus texensis, Lycopus europaeus, Lycopus lucidus, Marrubium cylleneum, Marrubium vulgare, Matricaria chamomilla, Matricaria discoidea, Mayaca fluviatilis, Medicago arborea, Meehania urticifolia, Melanoseris henryi, Mentha longifolia, Morinda morindoides, Myoporum tenuifolium, Ocimum gratissimum, Ocimum tenuiflorum, Oenothera triangulata, Onychium lucidum, Origanum vulgare, Orostachys japonica, Osmanthus fortunei, Osmanthus fragrans, Osmanthus heterophyllus, Ostericum sieboldii, Pallenis hierochuntica, Panzerina lanata, Parodiodoxa chionophila, Passiflora foetida, Passiflora menispermifolia, Passiflora palmeri, Passiflora pavonis, Passiflora pittieri, Passiflora sanguinolenta, Passiflora sexflora, Pedicularis rex, Pelargonium reniforme, Penstemon serrulatus, Perilla frutescens, Persicaria orientalis, Phagnalon rupestre, Phedimus kamtschaticus, Phlomis aurea, Phlomis nissolii, Phlomoides tuberosa, Phoenix loureiroi, Phyllocladus alpinus, Phyllostachys nigra, Pilosella officinarum, Plantago asiatica, Plantago lagopus, Platycodon grandiflorus, Podocarpus fasciculus, Podocarpus nivalis, Polygonum aviculare, Portulaca oleracea, Potentilla anserina, Prunus mume, Pteris cretica, Pteris multifida, Pteris podophylla, Pyrrhopappus carolinianus, Pyrrosia serpens, Quercus macrocarpa, Ramirezella strobilophora, Reichardia tingitana, Reseda luteola, Retama raetam, Riccia fluitans, Robinsonia masafuerae, Rubus amabilis, Rumex acetosella, Salix acutifolia, Salix caprea, Salix cheilophila, Salix daphnoides, Salix gilgiana, Salix gracilistyla, Salix purpurea, Salvia albimaculata, Salvia atropatana, Salvia candelabrum, Salvia fruticosa, Salvia limbata, Salvia palaestina, Salvia tomentosa, Salvia verticillata, Sandersonia aurantiaca, Santolina pinnata, Satureja cuneifolia, Scoparia dulcis, Scorzonera laciniata, Sechium edule, Sedum sarmentosum, Silybum marianum, Smilax riparia, Solanum incanum, Sonchus capillaris, Sonchus maritimus, Sonchus mauritanicus, Sonchus oleraceus, Sonneratia caseolaris, Sophora flavescens, Stachys aegyptiaca, Stachys chrysantha, Stevia microchaeta, Stevia nepetifolia, Stevia rebaudiana, Syagrus romanzoffiana, Symphyotrichum eatonii, Symphyotrichum subulatum, Tanacetum corymbosum, Tanacetum parthenium, Tanacetum vulgare, Taraxacum mongolicum, Teucrium hircanicum, Teucrium polium, Tinospora crispa, Trachelospermum jasminoides, Trachycarpus fortunei, Trachycarpus wagnerianus, Tragopogon pratensis, Traxacum officinale , Trichosanthes kirilowii, Trifolium canescens, Trifolium pannonicum, Trifolium trichocephalum, Turgenia latifolia, Urospermum picroides, Veratrum grandiflorum, Verbascum lychnitis, Verbascum phlomoides, Verbascum sinaiticum, Verbascum songaricum, Verbena officinalis, Gymnanthemum amygdalinum, Veronica polita, Veronica fuhsii, Veronica officinalis, Veronica strictissima, Veronica thymoides, Vicia sativa, Vicia subvillosa, Viola reichenbachiana, Vitex altissima, Vitex negundo, Vitis aestivalis, Youngia japonica and Zostera marina. It was first documented in 1994 (PMID: 7875536). Based on a literature review a significant number of articles have been published on Luteolin 7-glucoside (PMID: 27719955) (PMID: 20127879) (PMID: 22741463) (PMID: 23019878).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306222119262D          

 32 35  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 14 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  1  0  0  0
 25 26  1  0  0  0  0
 22 27  1  6  0  0  0
 21 28  1  1  0  0  0
 20 29  1  6  0  0  0
 12 30  1  0  0  0  0
  4 31  1  0  0  0  0
  3 32  1  0  0  0  0
M  END

NP0043860
     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    2.6769   -0.3517    4.1570 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7475   -0.2599    2.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9337   -0.2684    2.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9840   -0.1661    0.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611   -0.1768    0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4772   -0.2873    0.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6772   -0.2971    0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6359   -0.1888   -1.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8544   -0.1992   -2.0747 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4194   -0.0765   -2.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3523    0.0317   -3.3770 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2427   -0.0709   -1.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8592   -0.0566    0.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6823   -0.0427    0.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5166    0.0739    0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7439    0.0944    0.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8642    0.2134   -0.1143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1829    0.2523    0.2816 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8555   -0.8349   -0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2222   -0.7214   -0.1114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9100   -2.0381   -0.3521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7188   -2.5295   -1.6231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7486    0.2739   -1.1181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8885    0.9153   -0.6883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6138    1.2393   -1.4329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7496    0.5659   -2.3002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8387    1.5609   -0.1786 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6053    2.1288    0.8123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8048   -0.0073    2.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3439   -0.1252    2.7968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2941   -0.2294    4.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5774   -0.1421    2.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8468   -0.3604    2.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5625   -0.3734    1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6338   -0.3860    0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8785   -0.1243   -3.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1082    0.0419   -4.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2861    0.0195   -1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5902    0.1530   -1.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3013    0.1751    1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4181   -0.4253    0.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6013   -2.7944    0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0076   -1.8906   -0.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5002   -2.2667   -2.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0061   -0.2903   -2.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6963    1.7158   -0.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9723    2.1385   -1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2725    1.1934   -2.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0601    2.3012   -0.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5084    3.1076    0.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7519    0.0018    2.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990   -0.2161    4.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 16 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32  2  1  0
 12  5  1  0
 32 14  1  0
 27 18  1  0
  3 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 15 39  1  0
 18 40  1  1
 20 41  1  1
 21 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  6
 24 46  1  0
 25 47  1  6
 26 48  1  0
 27 49  1  6
 28 50  1  0
 29 51  1  0
 31 52  1  0
M  END


  Mrv1652306222119262D          

 32 35  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 14 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  1  0  0  0
 25 26  1  0  0  0  0
 22 27  1  6  0  0  0
 21 28  1  1  0  0  0
 20 29  1  6  0  0  0
 12 30  1  0  0  0  0
  4 31  1  0  0  0  0
  3 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043860

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1

> <INCHI_KEY>
PEFNSGRTCBGNAN-QNDFHXLGSA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.3769

> <EXACT_MASS>
448.100561482

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.98453166897848

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

> <ALOGPS_LOGP>
0.58

> <JCHEM_LOGP>
0.1350557186666665

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.720961662761638

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.296801688115588

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343758667

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
107.0392

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
luteolin 7-O-glucoside

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043860
     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    2.6769   -0.3517    4.1570 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7475   -0.2599    2.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9337   -0.2684    2.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9840   -0.1661    0.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611   -0.1768    0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4772   -0.2873    0.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6772   -0.2971    0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6359   -0.1888   -1.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8544   -0.1992   -2.0747 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4194   -0.0765   -2.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3523    0.0317   -3.3770 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2427   -0.0709   -1.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8592   -0.0566    0.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6823   -0.0427    0.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5166    0.0739    0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7439    0.0944    0.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8642    0.2134   -0.1143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1829    0.2523    0.2816 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8555   -0.8349   -0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2222   -0.7214   -0.1114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9100   -2.0381   -0.3521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7188   -2.5295   -1.6231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7486    0.2739   -1.1181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8885    0.9153   -0.6883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6138    1.2393   -1.4329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7496    0.5659   -2.3002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8387    1.5609   -0.1786 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6053    2.1288    0.8123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8048   -0.0073    2.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3439   -0.1252    2.7968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2941   -0.2294    4.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5774   -0.1421    2.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8468   -0.3604    2.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5625   -0.3734    1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6338   -0.3860    0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8785   -0.1243   -3.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1082    0.0419   -4.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2861    0.0195   -1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5902    0.1530   -1.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3013    0.1751    1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4181   -0.4253    0.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6013   -2.7944    0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0076   -1.8906   -0.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5002   -2.2667   -2.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0061   -0.2903   -2.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6963    1.7158   -0.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9723    2.1385   -1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2725    1.1934   -2.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0601    2.3012   -0.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5084    3.1076    0.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7519    0.0018    2.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990   -0.2161    4.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 16 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32  2  1  0
 12  5  1  0
 32 14  1  0
 27 18  1  0
  3 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 15 39  1  0
 18 40  1  1
 20 41  1  1
 21 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  6
 24 46  1  0
 25 47  1  6
 26 48  1  0
 27 49  1  6
 28 50  1  0
 29 51  1  0
 31 52  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5   31                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13   30                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16    7                                                       
CONECT   18   14   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   29                                                  
CONECT   21   20   22   28                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   22                                                            
CONECT   28   21                                                            
CONECT   29   20                                                            
CONECT   30   12                                                            
CONECT   31    4                                                            
CONECT   32    3                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    NP0043860
HETATM    1  O1  UNL     1       2.677  -0.352   4.157  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.747  -0.260   2.909  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.934  -0.268   2.206  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.984  -0.166   0.834  1.00  0.00           C  
HETATM    5  C4  UNL     1       5.261  -0.177   0.097  1.00  0.00           C  
HETATM    6  C5  UNL     1       6.477  -0.287   0.709  1.00  0.00           C  
HETATM    7  C6  UNL     1       7.677  -0.297   0.013  1.00  0.00           C  
HETATM    8  C7  UNL     1       7.636  -0.189  -1.375  1.00  0.00           C  
HETATM    9  O2  UNL     1       8.854  -0.199  -2.075  1.00  0.00           O  
HETATM   10  C8  UNL     1       6.419  -0.077  -2.008  1.00  0.00           C  
HETATM   11  O3  UNL     1       6.352   0.032  -3.377  1.00  0.00           O  
HETATM   12  C9  UNL     1       5.243  -0.071  -1.275  1.00  0.00           C  
HETATM   13  O4  UNL     1       2.859  -0.057   0.175  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.682  -0.043   0.800  1.00  0.00           C  
HETATM   15  C11 UNL     1       0.517   0.074   0.076  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.744   0.094   0.672  1.00  0.00           C  
HETATM   17  O5  UNL     1      -1.864   0.213  -0.114  1.00  0.00           O  
HETATM   18  C13 UNL     1      -3.183   0.252   0.282  1.00  0.00           C  
HETATM   19  O6  UNL     1      -3.855  -0.835  -0.290  1.00  0.00           O  
HETATM   20  C14 UNL     1      -5.222  -0.721  -0.111  1.00  0.00           C  
HETATM   21  C15 UNL     1      -5.910  -2.038  -0.352  1.00  0.00           C  
HETATM   22  O7  UNL     1      -5.719  -2.530  -1.623  1.00  0.00           O  
HETATM   23  C16 UNL     1      -5.749   0.274  -1.118  1.00  0.00           C  
HETATM   24  O8  UNL     1      -6.889   0.915  -0.688  1.00  0.00           O  
HETATM   25  C17 UNL     1      -4.614   1.239  -1.433  1.00  0.00           C  
HETATM   26  O9  UNL     1      -3.750   0.566  -2.300  1.00  0.00           O  
HETATM   27  C18 UNL     1      -3.839   1.561  -0.179  1.00  0.00           C  
HETATM   28  O10 UNL     1      -4.605   2.129   0.812  1.00  0.00           O  
HETATM   29  C19 UNL     1      -0.805  -0.007   2.043  1.00  0.00           C  
HETATM   30  C20 UNL     1       0.344  -0.125   2.797  1.00  0.00           C  
HETATM   31  O11 UNL     1       0.294  -0.229   4.192  1.00  0.00           O  
HETATM   32  C21 UNL     1       1.577  -0.142   2.171  1.00  0.00           C  
HETATM   33  H1  UNL     1       4.847  -0.360   2.783  1.00  0.00           H  
HETATM   34  H2  UNL     1       6.563  -0.373   1.776  1.00  0.00           H  
HETATM   35  H3  UNL     1       8.634  -0.386   0.519  1.00  0.00           H  
HETATM   36  H4  UNL     1       8.878  -0.124  -3.071  1.00  0.00           H  
HETATM   37  H5  UNL     1       7.108   0.042  -4.029  1.00  0.00           H  
HETATM   38  H6  UNL     1       4.286   0.020  -1.801  1.00  0.00           H  
HETATM   39  H7  UNL     1       0.590   0.153  -1.008  1.00  0.00           H  
HETATM   40  H8  UNL     1      -3.301   0.175   1.370  1.00  0.00           H  
HETATM   41  H9  UNL     1      -5.418  -0.425   0.936  1.00  0.00           H  
HETATM   42  H10 UNL     1      -5.601  -2.794   0.426  1.00  0.00           H  
HETATM   43  H11 UNL     1      -7.008  -1.891  -0.169  1.00  0.00           H  
HETATM   44  H12 UNL     1      -6.500  -2.267  -2.176  1.00  0.00           H  
HETATM   45  H13 UNL     1      -6.006  -0.290  -2.038  1.00  0.00           H  
HETATM   46  H14 UNL     1      -6.696   1.716  -0.148  1.00  0.00           H  
HETATM   47  H15 UNL     1      -4.972   2.138  -1.958  1.00  0.00           H  
HETATM   48  H16 UNL     1      -3.272   1.193  -2.906  1.00  0.00           H  
HETATM   49  H17 UNL     1      -3.060   2.301  -0.466  1.00  0.00           H  
HETATM   50  H18 UNL     1      -4.508   3.108   0.889  1.00  0.00           H  
HETATM   51  H19 UNL     1      -1.752   0.002   2.573  1.00  0.00           H  
HETATM   52  H20 UNL     1      -0.599  -0.216   4.631  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   32
CONECT    3    4    4   33
CONECT    4    5   13
CONECT    5    6    6   12
CONECT    6    7   34
CONECT    7    8    8   35
CONECT    8    9   10
CONECT    9   36
CONECT   10   11   12   12
CONECT   11   37
CONECT   12   38
CONECT   13   14
CONECT   14   15   15   32
CONECT   15   16   39
CONECT   16   17   29   29
CONECT   17   18
CONECT   18   19   27   40
CONECT   19   20
CONECT   20   21   23   41
CONECT   21   22   42   43
CONECT   22   44
CONECT   23   24   25   45
CONECT   24   46
CONECT   25   26   27   47
CONECT   26   48
CONECT   27   28   49
CONECT   28   50
CONECT   29   30   51
CONECT   30   31   32   32
CONECT   31   52
END

NP0043860
     RDKit          3D

52 55  0  0  0  0  0  0  0  0999 V2000
    2.6769   -0.3517    4.1570 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7475   -0.2599    2.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9337   -0.2684    2.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9840   -0.1661    0.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611   -0.1768    0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4772   -0.2873    0.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6772   -0.2971    0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6359   -0.1888   -1.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8544   -0.1992   -2.0747 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4194   -0.0765   -2.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3523    0.0317   -3.3770 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2427   -0.0709   -1.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8592   -0.0566    0.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6823   -0.0427    0.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5166    0.0739    0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7439    0.0944    0.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8642    0.2134   -0.1143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1829    0.2523    0.2816 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8555   -0.8349   -0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2222   -0.7214   -0.1114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9100   -2.0381   -0.3521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7188   -2.5295   -1.6231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7486    0.2739   -1.1181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8885    0.9153   -0.6883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6138    1.2393   -1.4329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7496    0.5659   -2.3002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8387    1.5609   -0.1786 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6053    2.1288    0.8123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8048   -0.0073    2.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3439   -0.1252    2.7968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2941   -0.2294    4.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5774   -0.1421    2.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8468   -0.3604    2.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5625   -0.3734    1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6338   -0.3860    0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8785   -0.1243   -3.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1082    0.0419   -4.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2861    0.0195   -1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5902    0.1530   -1.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3013    0.1751    1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4181   -0.4253    0.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6013   -2.7944    0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0076   -1.8906   -0.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5002   -2.2667   -2.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0061   -0.2903   -2.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6963    1.7158   -0.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9723    2.1385   -1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2725    1.1934   -2.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0601    2.3012   -0.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5084    3.1076    0.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7519    0.0018    2.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990   -0.2161    4.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 16 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32  2  1  0
 12  5  1  0
 32 14  1  0
 27 18  1  0
  3 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 15 39  1  0
 18 40  1  1
 20 41  1  1
 21 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  6
 24 46  1  0
 25 47  1  6
 26 48  1  0
 27 49  1  6
 28 50  1  0
 29 51  1  0
 31 52  1  0
M  END

View in JSmol

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside	ChEBI
2-(3,4-Dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one	ChEBI
7-Glucoluteolin	ChEBI
7-Glucosylluteolin	ChEBI
7-O-beta-D-Glucosyl-5,7,3',4'-tetrahydroxyflavone	ChEBI
Cinaroside	ChEBI
Cynaroside	ChEBI
Luteolin 7-monoglucoside	ChEBI
Luteolin 7-O-glucopyranoside	ChEBI
Luteolin 7-O-glucoside	ChEBI
Luteolin-7-glucoside	ChEBI
Luteoloside	ChEBI
2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl b-D-glucopyranoside	Generator
2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl β-D-glucopyranoside	Generator
2-(3,4-Dihydroxyphenyl)-7-(b-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one	Generator
2-(3,4-Dihydroxyphenyl)-7-(β-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one	Generator
7-O-b-D-Glucosyl-5,7,3',4'-tetrahydroxyflavone	Generator
7-O-Β-D-glucosyl-5,7,3',4'-tetrahydroxyflavone	Generator
Daphneflavonoloside	HMDB
Flavopurposide	HMDB
Glucoluteolin	HMDB
Luteolin 7-O-beta-D-glucoside	HMDB
Luteolin 7-O-b-D-glucoside	HMDB
Luteolin 7-O-β-D-glucoside	HMDB
Nephrocizin	HMDB
Luteolin-7-O-monoglucoside	HMDB
Luteolin-7-O-beta-D-glucopyranoside	HMDB
Luteolin-7-beta-D-glucoside	HMDB
3',4',5,7-Tetrahydroxyflavone 7-beta-D-glucopyranoside	HMDB
3',4',5,7-Tetrahydroxyflavone 7-β-D-glucopyranoside	HMDB
3’,4’,5,7-tetrahydroxyflavone 7-β-D-glucopyranoside	HMDB
3',4',5-Trihydroxyflavone 7-O-beta-D-glucopyranoside	HMDB
3',4',5-Trihydroxyflavone 7-O-β-D-glucopyranoside	HMDB
3’,4’,5-trihydroxyflavone 7-O-β-D-glucopyranoside	HMDB
7-(beta-D-Glucosyloxy)-3',4',5-trihydroxyflavone	HMDB
7-(Β-D-glucosyloxy)-3',4',5-trihydroxyflavone	HMDB
7-(Β-D-glucosyloxy)-3’,4’,5-trihydroxyflavone	HMDB
7-O-beta-D-Glucosylluteolin	HMDB
7-O-Β-D-glucosylluteolin	HMDB
Luteolin 7-O-beta-D-glucopyranoside	HMDB
Luteolin 7-O-β-D-glucopyranoside	HMDB
Luteolin 7-O-beta-glucopyranoside	HMDB
Luteolin 7-O-β-glucopyranoside	HMDB
Luteolin 7-O-beta-glucoside	HMDB
Luteolin 7-O-β-glucoside	HMDB
Luteolin 7-beta-D-glucoside	HMDB
Luteolin 7-β-D-glucoside	HMDB
Luteolin 7-glucoside	ChEBI

Chemical Formula

C₂₁H₂₀O₁₁

Average Mass

448.3769 Da

Monoisotopic Mass

448.10056 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

luteolin 7-O-glucoside

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1

InChI Key

PEFNSGRTCBGNAN-QNDFHXLGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
A. elatiusa, A. lilacinum	LOTUS Database	35616633
Acacia caven	KNApSAcK Database	22123792
Acacia furcatispina	KNApSAcK Database	22123792
Achillea biebersteinii	LOTUS Database	35616633
Achillea collina	LOTUS Database	35616633
Achillea fragrantissima	LOTUS Database	35616633
Achillea millefolium	LOTUS Database	35616633
Achillea pannonica	LOTUS Database	35616633
Achillea santolina	LOTUS Database	35616633
Achyrocline satureioides	KNApSAcK Database	22123792
Acilepis saligna	LOTUS Database	35616633
Aechmea glomerata	KNApSAcK Database	22123792
Agastache foeniculum	LOTUS Database	35616633
Agrimonia eupatoria	LOTUS Database	35616633
Agrimonia pilosa var.japonica	KNApSAcK Database	22123792
Ailanthus altissima	LOTUS Database	35616633
Ajuga lupulina	LOTUS Database	35616633
Allium rotundum	LOTUS Database	35616633
Aloysia citrodora	LOTUS Database	35616633
Ammannia coccinea	LOTUS Database	35616633
Ammothamnus lehmanni Bge.	KNApSAcK Database	22123792
Ammothamnus lehmannii	LOTUS Database	35616633
Anastatica hierochuntica	LOTUS Database	35616633
Anethum graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Angelica keiskei	LOTUS Database	35616633
Antennaria dioica	LOTUS Database	35616633
Anthemis auriculata	LOTUS Database	35616633
Apium graveolens	FooDB	PHENOL EXPLORER
Apium graveolens var. secalinum	FooDB	PHENOL EXPLORER
Aquilegia ecalcarata	LOTUS Database	35616633
Arnica acaulis	LOTUS Database	35616633
Arnica angustifolia	LOTUS Database	35616633
Arnica chamissonis	LOTUS Database	35616633
Arnica cordifolia	LOTUS Database	35616633
Arnica gracilis	LOTUS Database	35616633
Arnica longifolia	LOTUS Database	35616633
Arnica mollis	LOTUS Database	35616633
Arnica sororia	LOTUS Database	35616633
Artabotrys hexapetalus	LOTUS Database	35616633
Artemisia annua	KNApSAcK Database	22123792
Artemisia assoana	LOTUS Database	35616633
Artemisia caucasica	LOTUS Database	35616633
Artemisia dracunculus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Artemisia palustris	LOTUS Database	35616633
Artemisia rupestris	LOTUS Database	35616633
Artemisia xerophytica	LOTUS Database	35616633
Arum maculatum	LOTUS Database	35616633
Asphodeline globifera	KNApSAcK Database	22123792
Asphodelus ramosus	LOTUS Database	35616633
Asteriscus graveolens	LOTUS Database	35616633
Asyneuma campanuloides	LOTUS Database	35616633
Bacopa monnieri	LOTUS Database	35616633
Bahiopsis deltoidea	LOTUS Database	35616633
Ballota acetabulosa	LOTUS Database	35616633
Ballota hirsuta	LOTUS Database	35616633
Bartsia alpina	LOTUS Database	35616633
Betula nigra	KNApSAcK Database	22123792
Bidens frondosa	LOTUS Database	35616633
Bidens tripartita	LOTUS Database	35616633
Biebersteinia multifida	LOTUS Database	35616633
Biebersteinia orphanidis	LOTUS Database	35616633
Bischofia javanica	LOTUS Database	35616633
Brandisia hancei	LOTUS Database	35616633
Broussonetia papyrifera	LOTUS Database	35616633
Bryum argenteum	LOTUS Database	35616633
Bryum capillare	LOTUS Database	35616633
Bryum pseudotriquetrum	LOTUS Database	35616633
Buddleja officinalis	LOTUS Database	35616633
Buphthalmum salicifolium	LOTUS Database	35616633
Campanula armena	LOTUS Database	35616633
Campanula lactiflora	LOTUS Database	35616633
Campanula ossetica	LOTUS Database	35616633
Campanula pendula	LOTUS Database	35616633
Campanula persicifolia	LOTUS Database	35616633
Canarium album	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Capsella bursa-pastoris	Plant	KNApSAcK
Capsicum annuum	KNApSAcK Database	22123792
Carallia brachiata	LOTUS Database	35616633
Carduus acanthoides	LOTUS Database	35616633
Carduus nutans	LOTUS Database	35616633
Carthamus lanatus	LOTUS Database	35616633
Carthamus tinctorius	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Caryopteris tangutica	LOTUS Database	35616633
Catalpa speciosa	LOTUS Database	35616633
Centaurea cyanus	LOTUS Database	35616633
Centaurea montana	LOTUS Database	35616633
Centaurea pseudoscabiosa	LOTUS Database	35616633
Cephalaria gigantea	LOTUS Database	35616633
Cephalotus follicularis	LOTUS Database	35616633
Chaerophyllum aureum	LOTUS Database	35616633
Chaerophyllum hirsutum	LOTUS Database	35616633
Chamaemelum nobile	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Chondrilla juncea	LOTUS Database	35616633
Chrozophora tinctoria	LOTUS Database	35616633
Chrysanthemum coronarium	LOTUS Database	35616633
Chrysanthemum indicum	KNApSAcK Database	22123792
Chrysanthemum morifolium	KNApSAcK Database	22123792
Chrysanthemum x morifolium	Plant	KNApSAcK
Chrysanthemum zawadskii	LOTUS Database	35616633
Cichorium intybus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cirsium heterophyllum	LOTUS Database	35616633
Cirsium palustre	LOTUS Database	35616633
Clerodendron serratum	KNApSAcK Database	22123792
Clinopodium umbrosum	LOTUS Database	35616633
Codonopsis clematidea	LOTUS Database	35616633
Codonopsis foetens	LOTUS Database	35616633
Codonopsis lanceolata	LOTUS Database	35616633
Codonopsis ovata	LOTUS Database	35616633
Colchicum speciosum	LOTUS Database	35616633
Colocasia esculenta	Plant	KNApSAcK
Conocephalum conicum	KNApSAcK Database	22123792
Coreopsis basalis	LOTUS Database	35616633
Cornulaca monacantha	LOTUS Database	35616633
Cotoneaster multiflorus	LOTUS Database	35616633
Cotula cinerea	LOTUS Database	35616633
Crepidomanes minutum	LOTUS Database	35616633
Crotalaria verrucosa	LOTUS Database	35616633
Cuminum cyminum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cuphea wrightii	LOTUS Database	35616633
Cyanthillium cinereum	LOTUS Database	35616633
Cyanthillium patulum	LOTUS Database	35616633
Cymophyllus fraseri	LOTUS Database	35616633
Cynara cardunculus	LOTUS Database	35616633
Cynara cornigera	LOTUS Database	35616633
Cynara scolymus	FooDB	PHENOL EXPLORER
Cynomorium songaricum	LOTUS Database	35616633
Cytisus hirsutus	LOTUS Database	35616633
Daphne gnidium	LOTUS Database	35616633
Daphne oleoides	LOTUS Database	35616633
Daucus carota	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota ssp. sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Dracocephalum multicaule	LOTUS Database	35616633
Dracocephalum nutans	LOTUS Database	35616633
Dracocephalum rupestre	KNApSAcK Database	22123792
Dracocephalum tanguticum	LOTUS Database	35616633
Echinop ritro	-	KNApSAcK
Elsholtzia ciliata	LOTUS Database	35616633
Elsholtzia rugulosa	LOTUS Database	35616633
Epimedium pubescens	LOTUS Database	35616633
Equisetum arvense	LOTUS Database	35616633
Eryngium campestre	LOTUS Database	35616633
Euphorbia humifusa	LOTUS Database	35616633
Euphorbia maculata	LOTUS Database	35616633
Ferula assa-foetida	LOTUS Database	35616633
Ferula varia	LOTUS Database	35616633
Foeniculum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Frullania dilatata	KNApSAcK Database	22123792
Frullania muscicola	LOTUS Database	35616633
Frullania tamarisci	KNApSAcK Database	22123792
Fuchsia colensoi	LOTUS Database	35616633
Fuchsia splendens	LOTUS Database	35616633
Galeopsis bifida	LOTUS Database	35616633
Galinsoga parviflora	LOTUS Database	35616633
Genista corsica	LOTUS Database	35616633
Genista lydia	LOTUS Database	35616633
Genista sessilifolia	LOTUS Database	35616633
Gentiana argentea	KNApSAcK Database	22123792
Gentiana arisanensis	LOTUS Database	35616633
Gentiana depressa	KNApSAcK Database	22123792
Gentiana elwesii	KNApSAcK Database	22123792
Gentiana pedicellata	KNApSAcK Database	22123792
Gentiana prolata	KNApSAcK Database	22123792
Gentiana sikkimensis	KNApSAcK Database	22123792
Gerbera jamesonii	LOTUS Database	35616633
Glechoma hederacea	LOTUS Database	35616633
Glycyrrhiza glabra	LOTUS Database	35616633
Gnaphalium affine	KNApSAcK Database	22123792
Gutierrezia wrightii	KNApSAcK Database	22123792
Gymnarrhena micrantha	LOTUS Database	35616633
Halenia corniculata	LOTUS Database	35616633
Halleria lucida	LOTUS Database	35616633
Helichrysum arenarium	LOTUS Database	35616633
Helichrysum graveolen	KNApSAcK Database	22123792
Helichrysum stoechas	LOTUS Database	35616633
Heteromera fuscata	LOTUS Database	35616633
Hieracium gymnocephalum	LOTUS Database	35616633
Hieracium naegelianum	LOTUS Database	35616633
Hordeum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Humulus japonicus	KNApSAcK Database	22123792
Humulus lupulus	LOTUS Database	35616633
Hymenaea palustris Ducke	KNApSAcK Database	22123792
Hyparrhenia hirta	LOTUS Database	35616633
Isoplexis chalcantha	LOTUS Database	35616633
Itoa orientalis	LOTUS Database	35616633
Ixeridium laevigatum	LOTUS Database	35616633
Ixeris tamagawaensis	LOTUS Database	35616633
Jacaranda decurrens	LOTUS Database	35616633
Lactuca formosana	LOTUS Database	35616633
Lactuca indica	KNApSAcK Database	22123792
Lactuca quercina L.	LOTUS Database	35616633
Lactuca serriola	LOTUS Database	35616633
Lactuca viminea	LOTUS Database	35616633
Lagotis brevituba	LOTUS Database	35616633
Lamyropsis cynaroides	LOTUS Database	35616633
Launaea capitata	LOTUS Database	35616633
Launaea lanifera	LOTUS Database	35616633
Lavandula dentata	LOTUS Database	35616633
Lawsonia inermis	LOTUS Database	35616633
Leiothrix curvifolia	LOTUS Database	35616633
Lens culinaris	FooDB	PHENOL EXPLORER
Lepidothamnus laxifolius	LOTUS Database	35616633
Leycesteria formosa	LOTUS Database	35616633
Libocedrus plumosa	LOTUS Database	35616633
Ligustrum vulgare	LOTUS Database	35616633
Limonium axillare	LOTUS Database	35616633
Linaria macroura	LOTUS Database	35616633
Linum grandiflorum	LOTUS Database	35616633
Lippia alba	LOTUS Database	35616633
Lippia graveolens	LOTUS Database	35616633
Lippia origanoides	LOTUS Database	35616633
Lippia sidoides	LOTUS Database	35616633
Lomatium dissectum	LOTUS Database	35616633
Lomelosia caucasica	LOTUS Database	35616633
Lonicera gracilipes	LOTUS Database	35616633
Lonicera japonica	LOTUS Database	35616633
Lotus uliginosus	LOTUS Database	35616633
Luetkea pectinata	LOTUS Database	35616633
Lupinus texensis	LOTUS Database	35616633
Lycopus europaeus	LOTUS Database	35616633
Lycopus lucidus	LOTUS Database	35616633
Marrubium cylleneum	LOTUS Database	35616633
Marrubium vulgare	LOTUS Database	35616633
Matricaria chamomilla	LOTUS Database	35616633
Matricaria discoidea	LOTUS Database	35616633
Matricaria recutita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mayaca fluviatilis	LOTUS Database	35616633
Medicago arborea	LOTUS Database	35616633
Meehania urticifolia	LOTUS Database	35616633
Melandrium album	KNApSAcK Database	22123792
Melanoseris henryi	LOTUS Database	35616633
Melissa officinalis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha aquatica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha aquatica L.	KNApSAcK Database	22123792
Mentha longifolia	LOTUS Database	35616633
Mentha piperitae	KNApSAcK Database	22123792
Mentha spicata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha x piperita	FooDB	PHENOL EXPLORER
Morinda morindoides	LOTUS Database	35616633
Myoporum tenuifolium	LOTUS Database	35616633
Nelumbo nucifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ocimum gratissimum	LOTUS Database	35616633
Ocimum tenuiflorum	LOTUS Database	35616633
Oenothera triangulata	LOTUS Database	35616633
Olea europaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Onopordum acanthium	KNApSAcK Database	22123792
Onychium lucidum	LOTUS Database	35616633
Origanum majorana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum vulgare	LOTUS Database	35616633
Orostachys japonica	LOTUS Database	35616633
Osmanthus fortunei	LOTUS Database	35616633
Osmanthus fragrans	LOTUS Database	35616633
Osmanthus heterophyllus	LOTUS Database	35616633
Ostericum sieboldii	LOTUS Database	35616633
Pallenis hierochuntica	LOTUS Database	35616633
Panzerina lanata	LOTUS Database	35616633
Parodiodoxa chionophila	LOTUS Database	35616633
Passiflora foetida	LOTUS Database	35616633
Passiflora menispermifolia	LOTUS Database	35616633
Passiflora palmeri	LOTUS Database	35616633
Passiflora pavonis	LOTUS Database	35616633
Passiflora pittieri	LOTUS Database	35616633
Passiflora sanguinolenta	LOTUS Database	35616633
Passiflora sexflora	LOTUS Database	35616633
Pedicularis rex	LOTUS Database	35616633
Pediomelum esculentum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pelargonium reniforme	LOTUS Database	35616633
Penstemon serrulatus	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Persicaria orientalis	LOTUS Database	35616633
Phagnalon rupestre	LOTUS Database	35616633
Phedimus kamtschaticus	LOTUS Database	35616633
Phlomis aurea	LOTUS Database	35616633
Phlomis brunneogaleata	KNApSAcK Database	22123792
Phlomis nissolii	LOTUS Database	35616633
Phlomoides tuberosa	LOTUS Database	35616633
Phoenix loureiroi	LOTUS Database	35616633
Phyllocladus alpinus	LOTUS Database	35616633
Phyllostachys nigra	LOTUS Database	35616633
Pilosella officinarum	LOTUS Database	35616633
Pimpinella anisum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Plantago asiatica	LOTUS Database	35616633
Plantago lagopus	LOTUS Database	35616633
Plantago major	KNApSAcK Database	22123792
Platycodon grandiflorus	LOTUS Database	35616633
Podocarpus fasciculus	LOTUS Database	35616633
Podocarpus nivalis	LOTUS Database	35616633
Polygonum aviculare	LOTUS Database	35616633
Polygonum cuspidatum	KNApSAcK Database	22123792
Portulaca oleracea	LOTUS Database	35616633
Potentilla anserina	LOTUS Database	35616633
Prunella vulgaris	KNApSAcK Database	22123792
Prunus mume	LOTUS Database	35616633
Pteris cretica	LOTUS Database	35616633
Pteris multifida	LOTUS Database	35616633
Pteris podophylla	LOTUS Database	35616633
Punica granatum	KNApSAcK Database	22123792
Pyrrhopappus carolinianus	LOTUS Database	35616633
Pyrrosia serpens	LOTUS Database	35616633
Pyrus communis	FooDB	18778075
Quercus macrocarpa	LOTUS Database	35616633
Ramirezella strobilophora	LOTUS Database	35616633
Reichardia tingitana (L.) Roth	LOTUS Database	35616633
Reseda luteola	LOTUS Database	35616633
Retama raetam	LOTUS Database	35616633
Riccia fluitans	LOTUS Database	35616633
Riccia fluitans L	KNApSAcK Database	22123792
Robinsonia masafuerae	LOTUS Database	35616633
Rubus amabilis	LOTUS Database	35616633
Rumex acetosella	LOTUS Database	35616633
Salix acutifolia	LOTUS Database	35616633
Salix caprea	LOTUS Database	35616633
Salix cheilophila	LOTUS Database	35616633
Salix daphnoides	LOTUS Database	35616633
Salix gilgiana	LOTUS Database	35616633
Salix gracilistyla	LOTUS Database	35616633
Salix purpurea	LOTUS Database	35616633
Salvia albimaculata	LOTUS Database	35616633
Salvia atropatana	LOTUS Database	35616633
Salvia candelabrum	LOTUS Database	35616633
Salvia fruticosa	LOTUS Database	35616633
Salvia limbata	LOTUS Database	35616633
Salvia officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia palaestina	LOTUS Database	35616633
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia tomentosa	LOTUS Database	35616633
Salvia verticillata	LOTUS Database	35616633
Sandersonia aurantiaca	LOTUS Database	35616633
Santolina chamaecyperissus	KNApSAcK Database	22123792
Santolina pinnata	LOTUS Database	35616633
Satureja cuneifolia	LOTUS Database	35616633
Saussurea medusa	KNApSAcK Database	22123792
Schizonepeta tenuifolia	KNApSAcK Database	22123792
Scoparia dulcis	LOTUS Database	35616633
Scorzonera laciniata	LOTUS Database	35616633
Scutellaria oreophila	KNApSAcK Database	22123792
Sechium edule	LOTUS Database	35616633
Sedum sarmentosum	LOTUS Database	35616633
Silybum marianum	LOTUS Database	35616633
Smilax riparia	LOTUS Database	35616633
Solanum incanum	LOTUS Database	35616633
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sonchus capillaris	LOTUS Database	35616633
Sonchus maritimus	LOTUS Database	35616633
Sonchus mauritanicus	LOTUS Database	35616633
Sonchus oleraceus	LOTUS Database	35616633
Sonneratia caseolaris	LOTUS Database	35616633
Sophora flavescens	LOTUS Database	35616633
Spiraea hypericifolia	KNApSAcK Database	22123792
Stachys aegyptiaca	LOTUS Database	35616633
Stachys chrysantha	LOTUS Database	35616633
Stevia microchaeta	LOTUS Database	35616633
Stevia nepetifolia	LOTUS Database	35616633
Stevia rebaudiana	LOTUS Database	35616633
Syagrus romanzoffiana	LOTUS Database	35616633
Symphyotrichum eatonii	LOTUS Database	35616633
Symphyotrichum subulatum	LOTUS Database	35616633
Tanacetum corymbosum	LOTUS Database	35616633
Tanacetum parthenium	LOTUS Database	35616633
Tanacetum vulgare	LOTUS Database	35616633
Taraxacum mongolicum	LOTUS Database	35616633
Taraxacum officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tessaria dodoneifolia	KNApSAcK Database	22123792
Teucrium hircanicum	LOTUS Database	35616633
Teucrium polium	LOTUS Database	35616633
Thelesperma megapotamicum	KNApSAcK Database	22123792
Theobroma cacao	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Theobroma cacao L.	KNApSAcK Database	22123792
Thymus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tinospora crispa	LOTUS Database	35616633
Trachelospermum jasminoides	LOTUS Database	35616633
Trachycarpus fortunei	LOTUS Database	35616633
Trachycarpus wagnerianus	LOTUS Database	35616633
Tragopogon pratensis	LOTUS Database	35616633
Traxacum officinale	-	KNApSAcK
Trichosanthes kirilowii	LOTUS Database	35616633
Trifolium canescens	LOTUS Database	35616633
Trifolium pannonicum	LOTUS Database	35616633
Trifolium trichocephalum	LOTUS Database	35616633
Turgenia latifolia	LOTUS Database	35616633
Urospermum picroides	LOTUS Database	35616633
Valeriana chionophila	KNApSAcK Database	22123792
Valeriana fedtschenkoi	KNApSAcK Database	22123792
Veratrum grandiflorum	LOTUS Database	35616633
Verbascum lychnitis	LOTUS Database	35616633
Verbascum phlomoides	LOTUS Database	35616633
Verbascum sinaiticum	LOTUS Database	35616633
Verbascum songaricum	LOTUS Database	35616633
Verbena officinalis	LOTUS Database	35616633
Vernonia amygdalina	LOTUS Database	35616633
Veronica didyma	LOTUS Database	35616633
Veronica fuhsii	LOTUS Database	35616633
Veronica officinalis	LOTUS Database	35616633
Veronica peregrina L.	KNApSAcK Database	22123792
Veronica spicata	KNApSAcK Database	22123792
Veronica strictissima	LOTUS Database	35616633
Veronica thymoides	LOTUS Database	35616633
Veronica thymoides ssp.pseudocinerea	KNApSAcK Database	22123792
Veronicastrum sibiricum	KNApSAcK Database	22123792
Vicia sativa	LOTUS Database	35616633
Vicia subvillosa	LOTUS Database	35616633
Viola reichenbachiana	LOTUS Database	35616633
Vitex altissima	LOTUS Database	35616633
Vitex negundo	LOTUS Database	35616633
Vitis aestivalis	LOTUS Database	35616633
Wurmbea dioica F.Muell.	KNApSAcK Database	22123792
Youngia japonica	LOTUS Database	35616633
Zostera marina	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Oxane
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:27994 )
monosaccharide derivative (CHEBI:27994 )
glycosyloxyflavone (CHEBI:27994 )
trihydroxyflavone (CHEBI:27994 )
flavones (C03951 )
Flavones and Flavonols (C03951 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	838.10 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2888 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.090 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	0.58	ALOGPS
logP	0.14	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.04 m³·mol⁻¹	ChemAxon
Polarizability	42.98 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035588

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

LUTEOLIN-7-O-BETA-D-GLUCOSIDE

BiGG ID

Not Available

Wikipedia Link

Cynaroside

METLIN ID

Not Available

PubChem Compound

5280637

PDB ID

Not Available

ChEBI ID

27994

Good Scents ID

rw1699821

References

General References

Blunder M, Orthaber A, Bauer R, Bucar F, Kunert O: Efficient identification of flavones, flavanones and their glycosides in routine analysis via off-line combination of sensitive NMR and HPLC experiments. Food Chem. 2017 Mar 1;218:600-609. doi: 10.1016/j.foodchem.2016.09.077. Epub 2016 Sep 13. [PubMed:27719955 ]
Azevedo MF, Camsari C, Sa CM, Lima CF, Fernandes-Ferreira M, Pereira-Wilson C: Ursolic acid and luteolin-7-glucoside improve lipid profiles and increase liver glycogen content through glycogen synthase kinase-3. Phytother Res. 2010 Jun;24 Suppl 2:S220-4. doi: 10.1002/ptr.3118. [PubMed:20127879 ]
Sun Y, Ma X, Liu J: [Compounds from fraction with cardiovascular activity of Chrysanthemum indicum]. Zhongguo Zhong Yao Za Zhi. 2012 Jan;37(1):61-5. [PubMed:22741463 ]
Sun J, Huang Y, Sun G, Sun X, Qin M, Zhao D: [Study on in vitro antioxidant activity of flavonoids contained in Hebei balmy chrysanthemum and structure-activity relationship]. Zhongguo Zhong Yao Za Zhi. 2012 Jul;37(13):1958-62. [PubMed:23019878 ]
Rump AF, Schussler M, Acar D, Cordes A, Theisohn M, Rosen R, Klaus W, Fricke U: Functional and antiischemic effects of luteolin-7-glucoside in isolated rabbit hearts. Gen Pharmacol. 1994 Oct;25(6):1137-42. doi: 10.1016/0306-3623(94)90129-5. [PubMed:7875536 ]

Showing NP-Card for Cynaroside (NP0043860)

MOL for NP0043860 (Cynaroside)

3D MOL for NP0043860 (Cynaroside)

3D SDF for NP0043860 (Cynaroside)

3D-SDF for NP0043860 (Cynaroside)

PDB for NP0043860 (Cynaroside)

3D PDB for NP0043860 (Cynaroside)

SMILES for NP0043860 (Cynaroside)

INCHI for NP0043860 (Cynaroside)

Structure for NP0043860 (Cynaroside)

3D Structure for NP0043860 (Cynaroside)