NP-MRD: Showing NP-Card for (-)-friedelin (NP0170040)

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Record Information

Version

2.0

Created at

2022-09-03 06:06:24 UTC

Updated at

2022-09-03 06:06:24 UTC

NP-MRD ID

NP0170040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-friedelin

Description

Friedelin, also known as friedelan-3-one, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (-)-friedelin is found in Acer mandshuricum, Adansonia digitata, Adenophora wawreana, Ageratina glechonophylla, Ageratum conyzoides, Aglaomorpha quercifolia, Alchornea latifolia, Alsophila podophylla, Anchietea pyrifolia, Anchietea salutaris, Ardisia japonica, Artemisia annua, Artemisia argyi, Artemisia feddei, Artemisia lancea, Artemisia roxburghiana, Aster indicus, Aster koraiensis, Aster poliothamnus, Aster tataricus, Atalantia racemosa, Athrixia elata, Aucuba japonica, Autonoe madeirensis, Baccharis boliviensis, Baccharis patagonica, Baccharis tricuneata, Balanops australiana, Bambusa chungii, Bazzania japonica, Bazzania tridens, Begonia malabarica, Bidens pilosa, Bischofia javanica, Bistorta officinalis, Bridelia ferruginea, Bridelia ovata, Bulbophyllum vaginatum, Caesalpinia minax, Callisthene major, Calophyllum brasiliense, Calophyllum gracilipes, Calophyllum inophyllum, Calophyllum soulattri, Calophyllum teysmannii, Calophyllum verticillatum, Cannabis sativa, Caraipa densifolia, Casearia membranacea, Castanopsis eyrei, Catha edulis, Celastrus hindsii, Celastrus hypoleucus, Cheiropleuria bicuspis, Cichorium intybus, Cissus quadrangularis, Citrus aurantium, Citrus maxima, Citrus medica, Citrus unshiu, Clematis montana, Clerodendrum bungei, Clerodendrum cyrtophyllum, Clerodendrum mandarinorum, Clusia multiflora, Clusia nemorosa, Clusia paralicola, Codonopsis pilosula, Combretum imberbe, Cornus capitata, Cratoxylum arborescens, Cratoxylum cochinchinense, Crossopetalum parviflorum, Cymbidium aloifolium, Vincetoxicum hirundinaria, Dalbergia monetaria, Daldinia concentrica, Damnacanthus indicus, Dendrobium densiflorum, Dendropanax trifidus, Dialium excelsum, Dichrostachys cinerea, Dimocarpus longan, Diospyros buxifolia, Diospyros eriantha, Diospyros maritima, Diospyros virginiana, Diploknema butyracea, Dischidia formosana, Dittrichia viscosa, Drypetes gossweileri, Drypetes inaequalis, Drypetes laciniata, Putranjiva roxburghii, Duhaldea cappa, Elliottia paniculata, Endodesmia calophylloides, Eremanthus veadeiroensis, Erica arborea, Erigeron canadensis, Erythrophleum fordii, Eschenbachia blinii, Eugenia uniflora, Euonymus alatus, Euonymus japonicus, Euphorbia drupifera, Euphorbia hirta, Euphorbia maculata, Euphorbia rothiana, Euphorbia sapinii, Euphorbia segetalis, Euphorbia tortilis, Evernia prunastri, Ferula jaeschkeana, Ficus benjamina, Ficus cordata, Ganoderma applanatum, Garcinia acuminata, Garcinia celebica, Garcinia dulcis, Garcinia intermedia, Garcinia macrophylla, Garcinia mangostana, Garcinia nigrolineata, Garcinia opaca, Garcinia prainiana, Garcinia smeathmannii, Garcinia speciosa, Garcinia spicata, Garcinia staudtii, Garcinia xanthochymus, Globba racemosa, Glochidion puberum, Glochidion zeylanicum, Glycydendron amazonicum, Goniothalamus thwaitesii, Guazuma ulmifolia, Guilandina bonduc, Gymnosporia cassinoides, Gynura japonica, Gyrinops walla, Haploclathra paniculata, Haplopappus foliosus, Harrisonia abyssinica, Harungana madagascariensis, Heliotropium ellipticum, Heliotropium marifolium, Hydrangea chinensis, Hypericum ascyron, Mesosphaerum suaveolens, Isocoma pluriflora, Jacobaea minuta, Jatropha curcas, Jatropha maheshwarii, Liochlaena subulata, Kielmeyera elata, Kielmeyera lathrophyton, Kielmeyera pumila, Kleinia galpinii, Larix kaempferi, Leucosyke quadrinervia, Ligularia dolichobotrys, Ligularia veitchiana, Linaria saxatilis, Lumnitzera racemosa, Lychnophora ericoides, Lydenburgia cassinoides, Macaranga tanarius, Machilus zuihoensis, Mallotus apelta, Mallotus macrostachyus, Mallotus pallidus, Mallotus philippensis, Mallotus repandus, Mammea africana, Mammea americana, Mangifera indica, Gymnosporia diversifolia, Monteverdia rigida, Maytenus salicifolia, Mesua ferrea, Microtropis triflora, Mikania glomerata, Mikania triangularis, Monteverdia ilicifolia, Monteverdia robusta, Morella rubra, Morus alba, Murraya euchrestifolia, Myrianthus serratus, Nyctanthes arbor-tristis, Olearia paniculata, Ophiorrhiza japonica, Oreocnide frutescens, Orixa japonica, Ouratea castaneifolia, Pachysandra terminalis, Peltophorum dubium, Pentaclethra eetveldeana, Peritassa campestris, Peritassa laevigata, Phellinus pomaceus, Photinia lucida, Phyllanthus flexuosus, Phyllanthus reticulatus, Phyllanthus urinaria, Phyllostachys edulis, Picris hieracioides, Pinus luchuensis, Piper schmidtii, Piper umbellatum, Piranhea mexicana, Plenckia populnea, Pleopeltis polypodioides, Pleurostylia opposita, Plicanthus hirtellus, Polyporus umbellatus, Portulaca oleracea, Pourouma guianensis, Protium heptaphyllum, Prunus africana, Psorospermum tenuifolium, Pygeum topengii, Quercus glauca, Quercus suber, Raulinoa echinata, Rhododendron barbatum, Rhododendron aureum, Rhododendron ferrugineum, Rhododendron formosanum, Rhododendron luteum, Rhododendron schlippenbachii, Rhodomyrtus tomentosa, Ruscus aculeatus, Salacia beddomei, Salacia chinensis, Salacia petenensis, Salvia fruticosa, Santiria trimera, Scolopia spinosa, Scoparia dulcis, Semialarium mexicanum, Senna obtusifolia, Senna siamea, Sorbus americana, Sorbus tianschanica, Sphagneticola trilobata, Spiraea formosana, Swertia corymbosa, Syzygium formosanum, Syzygium grande, Talipariti tiliaceum, Terminalia alata, Terminalia glabrescens, Terminalia hylodendron, Tillandsia usneoides, Tovomita brasiliensis, Triadica sebifera, Tripetalum cymosum, Tripterygium wilfordii, Triumfetta rhomboidea, Ulmus davidiana, Ulmus pumila, Vaccinium bracteatum, Pentanema indicum, Viguiera decurrens, Vismia laurentii, Vitex peduncularis, Volkameria inermis, Xerosicyos danguyi, Xylosma longifolia, Zanthoxylum ailanthoides and Zanthoxylum schinifolium. (-)-friedelin was first documented in 2022 (PMID: 35965943). Based on a literature review a significant number of articles have been published on friedelin (PMID: 35889247) (PMID: 35997666) (PMID: 35889382) (PMID: 35678514) (PMID: 35631456) (PMID: 35624724).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032208062D          

 31 35  0  0  1  0            999 V2000
   -0.1105   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1105   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9337   -3.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8522   -3.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1895   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  7 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END

     RDKit          3D

 81 85  0  0  0  0  0  0  0  0999 V2000
    6.0090   -1.5284   -0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7323   -1.2303    0.4104 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9025   -0.8837    1.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2767   -1.7864    2.5823 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6617    0.4342    2.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6521    1.2657    1.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9758    0.3786    0.6992 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6741    0.9611    0.1325 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9351    2.2673   -0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8034    1.2062    1.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6548    1.1609    1.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1033   -0.0447    0.2856 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8122   -1.2637    1.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5695    0.1478   -0.0286 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3488    0.3333    1.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8401    0.2691    1.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4154    1.5278    0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4459    0.1538    2.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2874   -0.9413    0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1573   -1.7668   -0.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1172   -0.8902   -0.9742 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8889   -0.2500   -2.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0954   -1.8045   -1.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7470   -1.2683   -1.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488   -0.0358   -1.0243 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6120    1.1529   -1.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1209   -0.1104   -0.7394 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9874   -0.2826   -1.9405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3113   -0.8201   -1.4937 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9122   -0.1433   -0.3170 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9325    0.8545   -0.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0451   -1.0522   -1.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9059   -1.2849    0.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1085   -2.6346   -0.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0786   -2.1345    0.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6420    0.9520    2.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2872    0.3244    3.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8759    1.6776    2.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1958    2.1185    1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -0.5124    1.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0379    2.9307   -0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6325    2.8424    0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4022    2.2667   -1.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0208    2.2523    1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0972    0.5538    2.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1746    1.0780    2.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0416    2.1200    0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7205   -1.7238    1.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1359   -1.0462    1.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3369   -2.0968    0.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6405    1.1278   -0.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1367    1.3836    1.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0949   -0.3159    2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6239    2.2490    0.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1351    2.0403    1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9700    1.2665   -0.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4749    0.5695    2.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8475    0.8128    3.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4255   -0.8974    2.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9349   -0.6158   -0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9351   -1.6186    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7081   -2.4599    0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5906   -2.4032   -1.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8545   -0.7350   -2.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2960   -0.3771   -3.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9756    0.8479   -1.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892   -2.1655   -2.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0748   -2.7683   -0.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0049   -2.0910   -1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5585   -1.0503   -2.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0175    2.0352   -1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3237    1.5040   -2.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3097    0.9222   -2.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2595   -1.0808   -0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5103   -1.0871   -2.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1251    0.5744   -2.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1800   -1.9242   -1.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0082   -0.7615   -2.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6436    1.8954   -0.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1607    0.6831   -1.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9239    0.7462   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7 30  1  0
 30 31  1  6
 30 29  1  0
 29 28  1  0
 28 27  1  0
 27  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  6
 30  2  1  0
 25 27  1  0
  8  7  1  0
 25 12  1  0
 21 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  1
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  1
 31 79  1  0
 31 80  1  0
 31 81  1  0
 29 77  1  0
 29 78  1  0
 28 75  1  0
 28 76  1  0
 27 74  1  1
  9 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 13 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  6
 15 52  1  0
 15 53  1  0
 17 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  0
 18 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  0
 20 63  1  0
 22 64  1  0
 22 65  1  0
 22 66  1  0
 23 67  1  0
 23 68  1  0
 24 69  1  0
 24 70  1  0
 26 71  1  0
 26 72  1  0
 26 73  1  0
M  END


  Mrv1652309032208062D          

 31 35  0  0  1  0            999 V2000
   -0.1105   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1105   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9337   -3.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8522   -3.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1895   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  7 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0170040

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@@]2(C)CC[C@@]2(C)[C@@H]3CC(C)(C)CC[C@]3(C)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20,22-24H,9-19H2,1-8H3/t20-,22+,23-,24+,26+,27+,28-,29+,30-/m0/s1

> <INCHI_KEY>
OFMXGFHWLZPCFL-SVRPQWSVSA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.729

> <EXACT_MASS>
426.38616623

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
53.85442310218272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethyl-docosahydropicen-3-one

> <ALOGPS_LOGP>
6.66

> <JCHEM_LOGP>
8.116280839333331

> <ALOGPS_LOGS>
-7.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.416465990819413

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
130.20909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.01e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
friedlein

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.206 -11.137   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.746  -8.470   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.644  -7.136   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.076  -5.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.791  -6.610   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.574 -11.137   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   30                                                  
CONECT    8    7    9   10   27                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   25                                             
CONECT   13   12                                                            
CONECT   14   12   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   14   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   12   26   27                                             
CONECT   26   25                                                            
CONECT   27   25    8   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    7    2   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
(-)-Friedelin	ChEBI
D:A-friedooleanan-3-one	ChEBI
Friedelan-3-one	ChEBI
Friedeline	ChEBI
Friedelanone	MeSH

Chemical Formula

C₃₀H₅₀O

Average Mass

426.7290 Da

Monoisotopic Mass

426.38617 Da

IUPAC Name

(4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethyl-docosahydropicen-3-one

Traditional Name

friedlein

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@@]2(C)CC[C@@]2(C)[C@@H]3CC(C)(C)CC[C@]3(C)CC[C@]12C

InChI Identifier

InChI=1S/C30H50O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20,22-24H,9-19H2,1-8H3/t20-,22+,23-,24+,26+,27+,28-,29+,30-/m0/s1

InChI Key

OFMXGFHWLZPCFL-SVRPQWSVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acer mandshuricum	LOTUS Database	35616633
Adansonia digitata	LOTUS Database	35616633
Adenophora wawreana	LOTUS Database	35616633
Ageratina glechonophylla	LOTUS Database	35616633
Ageratum conyzoides	LOTUS Database	35616633
Aglaomorpha quercifolia	LOTUS Database	35616633
Alchornea latifolia	LOTUS Database	35616633
Alsophila podophylla	LOTUS Database	35616633
Anchietea pyrifolia	LOTUS Database	35616633
Anchietea salutaris	LOTUS Database	35616633
Ardisia japonica	LOTUS Database	35616633
Artemisia annua	LOTUS Database	35616633
Artemisia argyi	LOTUS Database	35616633
Artemisia feddei	LOTUS Database	35616633
Artemisia lancea	LOTUS Database	35616633
Artemisia roxburghiana	LOTUS Database	35616633
Aster indicus	LOTUS Database	35616633
Aster koraiensis	LOTUS Database	35616633
Aster poliothamnus	LOTUS Database	35616633
Aster tataricus	LOTUS Database	35616633
Atalantia racemosa	LOTUS Database	35616633
Athrixia elata	LOTUS Database	35616633
Aucuba japonica	LOTUS Database	35616633
Autonoe madeirensis	LOTUS Database	35616633
Baccharis boliviensis	LOTUS Database	35616633
Baccharis patagonica	LOTUS Database	35616633
Baccharis tricuneata	LOTUS Database	35616633
Balanops australiana	LOTUS Database	35616633
Bambusa chungii	LOTUS Database	35616633
Bazzania japonica	LOTUS Database	35616633
Bazzania tridens	LOTUS Database	35616633
Begonia malabarica	LOTUS Database	35616633
Bidens pilosa	LOTUS Database	35616633
Bischofia javanica	LOTUS Database	35616633
Bistorta officinalis	LOTUS Database	35616633
Bridelia ferruginea	LOTUS Database	35616633
Bridelia ovata	LOTUS Database	35616633
Bulbophyllum vaginatum	LOTUS Database	35616633
Caesalpinia minax	LOTUS Database	35616633
Callisthene major	LOTUS Database	35616633
Calophyllum brasiliense	LOTUS Database	35616633
Calophyllum gracilipes	LOTUS Database	35616633
Calophyllum inophyllum	LOTUS Database	35616633
Calophyllum soulattri	LOTUS Database	35616633
Calophyllum teysmannii	LOTUS Database	35616633
Calophyllum verticillatum	LOTUS Database	35616633
Cannabis sativa	LOTUS Database	35616633
Caraipa densifolia	LOTUS Database	35616633
Casearia membranacea	LOTUS Database	35616633
Castanopsis eyrei	LOTUS Database	35616633
Catha edulis	LOTUS Database	35616633
Celastrus hindsii	LOTUS Database	35616633
Celastrus hypoleucus	LOTUS Database	35616633
Cheiropleuria bicuspis	LOTUS Database	35616633
Cichorium intybus	LOTUS Database	35616633
Cissus quadrangularis	LOTUS Database	35616633
Citrus aurantium	LOTUS Database	35616633
Citrus maxima	LOTUS Database	35616633
Citrus medica	LOTUS Database	35616633
Citrus unshiu	LOTUS Database	35616633
Clematis montana	LOTUS Database	35616633
Clerodendrum bungei	LOTUS Database	35616633
Clerodendrum cyrtophyllum	LOTUS Database	35616633
Clerodendrum mandarinorum	LOTUS Database	35616633
Clusia multiflora	LOTUS Database	35616633
Clusia nemorosa	LOTUS Database	35616633
Clusia paralicola	LOTUS Database	35616633
Codonopsis pilosula	LOTUS Database	35616633
Combretum imberbe	LOTUS Database	35616633
Cornus capitata	LOTUS Database	35616633
Cratoxylum arborescens	LOTUS Database	35616633
Cratoxylum cochinchinense	LOTUS Database	35616633
Crossopetalum parviflorum	LOTUS Database	35616633
Cymbidium aloifolium	LOTUS Database	35616633
Cynanchum vincetoxicum	LOTUS Database	35616633
Dalbergia monetaria	LOTUS Database	35616633
Daldinia concentrica	LOTUS Database	35616633
Damnacanthus indicus	LOTUS Database	35616633
Dendrobium densiflorum	LOTUS Database	35616633
Dendropanax trifidus	LOTUS Database	35616633
Dialium excelsum	LOTUS Database	35616633
Dichrostachys cinerea	LOTUS Database	35616633
Dimocarpus longan	LOTUS Database	35616633
Diospyros buxifolia	LOTUS Database	35616633
Diospyros eriantha	LOTUS Database	35616633
Diospyros maritima	LOTUS Database	35616633
Diospyros virginiana	LOTUS Database	35616633
Diploknema butyracea	LOTUS Database	35616633
Dischidia formosana	LOTUS Database	35616633
Dittrichia viscosa	LOTUS Database	35616633
Drypetes gossweileri	LOTUS Database	35616633
Drypetes inaequalis	LOTUS Database	35616633
Drypetes laciniata	LOTUS Database	35616633
Drypetes roxburghii	LOTUS Database	35616633
Duhaldea cappa	LOTUS Database	35616633
Elliottia paniculata	LOTUS Database	35616633
Endodesmia calophylloides	LOTUS Database	35616633
Eremanthus veadeiroensis	LOTUS Database	35616633
Erica arborea	LOTUS Database	35616633
Erigeron canadensis	LOTUS Database	35616633
Erythrophleum fordii	LOTUS Database	35616633
Eschenbachia blinii	LOTUS Database	35616633
Eugenia uniflora	LOTUS Database	35616633
Euonymus alatus	LOTUS Database	35616633
Euonymus japonicus	LOTUS Database	35616633
Euphorbia drupifera	LOTUS Database	35616633
Euphorbia hirta	LOTUS Database	35616633
Euphorbia maculata	LOTUS Database	35616633
Euphorbia rothiana	LOTUS Database	35616633
Euphorbia sapinii	LOTUS Database	35616633
Euphorbia segetalis	LOTUS Database	35616633
Euphorbia tortilis	LOTUS Database	35616633
Evernia prunastri	LOTUS Database	35616633
Ferula jaeschkeana	LOTUS Database	35616633
Ficus benjamina	LOTUS Database	35616633
Ficus cordata	LOTUS Database	35616633
Ganoderma applanatum	LOTUS Database	35616633
Garcinia acuminata	LOTUS Database	35616633
Garcinia celebica	LOTUS Database	35616633
Garcinia dulcis	LOTUS Database	35616633
Garcinia intermedia	LOTUS Database	35616633
Garcinia macrophylla	LOTUS Database	35616633
Garcinia mangostana	LOTUS Database	35616633
Garcinia nigrolineata	LOTUS Database	35616633
Garcinia opaca	LOTUS Database	35616633
Garcinia prainiana	LOTUS Database	35616633
Garcinia smeathmannii	LOTUS Database	35616633
Garcinia speciosa	LOTUS Database	35616633
Garcinia spicata	LOTUS Database	35616633
Garcinia staudtii	LOTUS Database	35616633
Garcinia xanthochymus	LOTUS Database	35616633
Globba racemosa	LOTUS Database	35616633
Glochidion puberum	LOTUS Database	35616633
Glochidion zeylanicum	LOTUS Database	35616633
Glycydendron amazonicum	LOTUS Database	35616633
Goniothalamus thwaitesii	LOTUS Database	35616633
Guazuma ulmifolia	LOTUS Database	35616633
Guilandina bonduc	LOTUS Database	35616633
Gymnosporia cassinoides	LOTUS Database	35616633
Gynura japonica	LOTUS Database	35616633
Gyrinops walla	LOTUS Database	35616633
Haploclathra paniculata	LOTUS Database	35616633
Haplopappus foliosus	LOTUS Database	35616633
Harrisonia abyssinica	LOTUS Database	35616633
Harungana madagascariensis	LOTUS Database	35616633
Heliotropium ellipticum	LOTUS Database	35616633
Heliotropium marifolium	LOTUS Database	35616633
Hydrangea chinensis	LOTUS Database	35616633
Hypericum ascyron	LOTUS Database	35616633
Hyptis suaveolens	LOTUS Database	35616633
Isocoma wrightii	LOTUS Database	35616633
Jacobaea minuta	LOTUS Database	35616633
Jatropha curcas	LOTUS Database	35616633
Jatropha maheshwarii	LOTUS Database	35616633
Jungermannia subulata	LOTUS Database	35616633
Kielmeyera elata	LOTUS Database	35616633
Kielmeyera lathrophyton	LOTUS Database	35616633
Kielmeyera pumila	LOTUS Database	35616633
Kleinia galpinii	LOTUS Database	35616633
Larix kaempferi	LOTUS Database	35616633
Leucosyke quadrinervia	LOTUS Database	35616633
Ligularia dolichobotrys	LOTUS Database	35616633
Ligularia veitchiana	LOTUS Database	35616633
Linaria saxatilis	LOTUS Database	35616633
Lumnitzera racemosa	LOTUS Database	35616633
Lychnophora ericoides	LOTUS Database	35616633
Lydenburgia cassinoides	LOTUS Database	35616633
Macaranga tanarius	LOTUS Database	35616633
Machilus zuihoensis	LOTUS Database	35616633
Mallotus apelta	LOTUS Database	35616633
Mallotus macrostachyus	LOTUS Database	35616633
Mallotus pallidus	LOTUS Database	35616633
Mallotus philippensis	LOTUS Database	35616633
Mallotus repandus	LOTUS Database	35616633
Mammea africana	LOTUS Database	35616633
Mammea americana	LOTUS Database	35616633
Mangifera indica	LOTUS Database	35616633
Maytenus diversifolia	LOTUS Database	35616633
Maytenus rigida	LOTUS Database	35616633
Maytenus salicifolia	LOTUS Database	35616633
Mesua ferrea	LOTUS Database	35616633
Microtropis triflora	LOTUS Database	35616633
Mikania glomerata	LOTUS Database	35616633
Mikania triangularis	LOTUS Database	35616633
Monteverdia ilicifolia	LOTUS Database	35616633
Monteverdia robusta	LOTUS Database	35616633
Morella rubra	LOTUS Database	35616633
Morus alba	LOTUS Database	35616633
Murraya euchrestifolia	LOTUS Database	35616633
Myrianthus serratus	LOTUS Database	35616633
Nyctanthes arbor-tristis	LOTUS Database	35616633
Olearia paniculata	LOTUS Database	35616633
Ophiorrhiza japonica	LOTUS Database	35616633
Oreocnide frutescens	LOTUS Database	35616633
Orixa japonica	LOTUS Database	35616633
Ouratea castaneifolia	LOTUS Database	35616633
Pachysandra terminalis	LOTUS Database	35616633
Peltophorum dubium	LOTUS Database	35616633
Pentaclethra eetveldeana	LOTUS Database	35616633
Peritassa campestris	LOTUS Database	35616633
Peritassa laevigata	LOTUS Database	35616633
Phellinus pomaceus	LOTUS Database	35616633
Photinia lucida	LOTUS Database	35616633
Phyllanthus flexuosus	LOTUS Database	35616633
Phyllanthus reticulatus	LOTUS Database	35616633
Phyllanthus urinaria	LOTUS Database	35616633
Phyllostachys edulis	LOTUS Database	35616633
Picris hieracioides	LOTUS Database	35616633
Pinus luchuensis	LOTUS Database	35616633
Piper schmidtii	LOTUS Database	35616633
Piper umbellatum	LOTUS Database	35616633
Piranhea mexicana	LOTUS Database	35616633
Plenckia populnea	LOTUS Database	35616633
Pleopeltis polypodioides	LOTUS Database	35616633
Pleurostylia opposita	LOTUS Database	35616633
Plicanthus hirtellus	LOTUS Database	35616633
Polyporus umbellatus	LOTUS Database	35616633
Portulaca oleracea	LOTUS Database	35616633
Pourouma guianensis	LOTUS Database	35616633
Protium heptaphyllum	LOTUS Database	35616633
Prunus africana	LOTUS Database	35616633
Psorospermum tenuifolium	LOTUS Database	35616633
Pygeum topengii	LOTUS Database	35616633
Quercus glauca	LOTUS Database	35616633
Quercus suber	LOTUS Database	35616633
Raulinoa echinata	LOTUS Database	35616633
Rhododendron barbatum	LOTUS Database	35616633
Rhododendron chrysanthum	LOTUS Database	35616633
Rhododendron ferrugineum	LOTUS Database	35616633
Rhododendron formosanum	LOTUS Database	35616633
Rhododendron luteum	LOTUS Database	35616633
Rhododendron schlippenbachii	LOTUS Database	35616633
Rhodomyrtus tomentosa	LOTUS Database	35616633
Ruscus aculeatus	LOTUS Database	35616633
Salacia beddomei	LOTUS Database	35616633
Salacia chinensis	LOTUS Database	35616633
Salacia petenensis	LOTUS Database	35616633
Salvia fruticosa	LOTUS Database	35616633
Santiria trimera	LOTUS Database	35616633
Scolopia spinosa	LOTUS Database	35616633
Scoparia dulcis	LOTUS Database	35616633
Semialarium mexicanum	LOTUS Database	35616633
Senna obtusifolia	LOTUS Database	35616633
Senna siamea	LOTUS Database	35616633
Sorbus americana	LOTUS Database	35616633
Sorbus tianschanica	LOTUS Database	35616633
Sphagneticola trilobata	LOTUS Database	35616633
Spiraea formosana	LOTUS Database	35616633
Swertia corymbosa	LOTUS Database	35616633
Syzygium formosanum	LOTUS Database	35616633
Syzygium grande	LOTUS Database	35616633
Talipariti tiliaceum	LOTUS Database	35616633
Terminalia alata	LOTUS Database	35616633
Terminalia glabrescens	LOTUS Database	35616633
Terminalia hylodendron	LOTUS Database	35616633
Tillandsia usneoides	LOTUS Database	35616633
Tovomita brasiliensis	LOTUS Database	35616633
Triadica sebifera	LOTUS Database	35616633
Tripetalum cymosum	LOTUS Database	35616633
Tripterygium wilfordii	LOTUS Database	35616633
Triumfetta rhomboidea	LOTUS Database	35616633
Ulmus davidiana	LOTUS Database	35616633
Ulmus pumila	LOTUS Database	35616633
Vaccinium bracteatum	LOTUS Database	35616633
Vicoa indica	LOTUS Database	35616633
Viguiera decurrens	LOTUS Database	35616633
Vismia laurentii	LOTUS Database	35616633
Vitex peduncularis	LOTUS Database	35616633
Volkameria inermis	LOTUS Database	35616633
Xerosicyos danguyi	LOTUS Database	35616633
Xylosma longifolia	LOTUS Database	35616633
Zanthoxylum ailanthoides	LOTUS Database	35616633
Zanthoxylum schinifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

pentacyclic triterpenoid (CHEBI:5171 )
cyclic terpene ketone (CHEBI:5171 )
Hopanes (C08626 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.66	ALOGPS
logP	8.12	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	130.21 m³·mol⁻¹	ChemAxon
Polarizability	53.85 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Friedelin

METLIN ID

Not Available

PubChem Compound

91472

PDB ID

Not Available

ChEBI ID

5171

Good Scents ID

rw1247531

References

General References

Sang YL, Dai L, Wang P, Chen LJ, Jiao ML, Liu JY, Zhang NZ, Fan GW, Hao YJ, Wang XL: Investigation of insecticidal activity of two Rhododendron species on stored-product insects. J Plant Dis Prot (2006). 2022 Aug 9:1-12. doi: 10.1007/s41348-022-00654-z. [PubMed:35965943 ]
Sultana A, Hossain MJ, Kuddus MR, Rashid MA, Zahan MS, Mitra S, Roy A, Alam S, Sarker MMR, Naina Mohamed I: Ethnobotanical Uses, Phytochemistry, Toxicology, and Pharmacological Properties of Euphorbia neriifolia Linn. against Infectious Diseases: A Comprehensive Review. Molecules. 2022 Jul 8;27(14):4374. doi: 10.3390/molecules27144374. [PubMed:35889247 ]
Lizazman MA, Jong VYM, Chua P, Lim WK, Karunakaran T: Phytochemicals from Calophyllum canum Hook f. ex T. Anderson and their neuroprotective effects. Nat Prod Res. 2023 Jun;37(12):2043-2048. doi: 10.1080/14786419.2022.2116021. Epub 2022 Aug 23. [PubMed:35997666 ]
Sandhu M, Irfan HM, Shah SA, Ahmed M, Naz I, Akram M, Fatima H, Farooq AS: Friedelin Attenuates Neuronal Dysfunction and Memory Impairment by Inhibition of the Activated JNK/NF-kappaB Signalling Pathway in Scopolamine-Induced Mice Model of Neurodegeneration. Molecules. 2022 Jul 14;27(14):4513. doi: 10.3390/molecules27144513. [PubMed:35889382 ]
Essombe Malolo FA, Bellier Tabekoueng G, Dongmo Tekapi Tsopgni W, Nguemdjo Chimeze VW, Kenmogne Kouam A, Mas-Claret E, Langat MK, Ndom JC, Frese M, Sewald N, Duplex Wansi J: Chemical Constituents of the Stem Bark of the Hybrid Plant Citrus x paradisi Macfad. (Rutaceae). Chem Biodivers. 2022 Jul;19(7):e202101033. doi: 10.1002/cbdv.202101033. Epub 2022 Jun 9. [PubMed:35678514 ]
Falev DI, Ovchinnikov DV, Voronov IS, Faleva AV, Ul'yanovskii NV, Kosyakov DS: Supercritical Fluid Chromatography-Tandem Mass Spectrometry for Rapid Quantification of Pentacyclic Triterpenoids in Plant Extracts. Pharmaceuticals (Basel). 2022 May 20;15(5):629. doi: 10.3390/ph15050629. [PubMed:35631456 ]
Ferrini F, Donati Zeppa S, Fraternale D, Carrabs V, Annibalini G, Verardo G, Gorassini A, Albertini MC, Ismail T, Fimognari C, Sestili P: Characterization of the Biological Activity of the Ethanolic Extract from the Roots of Cannabis sativa L. Grown in Aeroponics. Antioxidants (Basel). 2022 Apr 27;11(5):860. doi: 10.3390/antiox11050860. [PubMed:35624724 ]
Li P, Fang X, Liang X: The complete chloroplast genome of Crepis rigescens (Cichorioideae), a traditional Chinese medicinal plant. Mitochondrial DNA B Resour. 2022 May 2;7(5):729-731. doi: 10.1080/23802359.2022.2068978. eCollection 2022. [PubMed:35528249 ]
Jiang H, Lin X, Liang W, Li Y, Yu X: Friedelin Alleviates the Pathogenesis of Collagenase-Induced Tendinopathy in Mice by Promoting the Selective Autophagic Degradation of p65. Nutrients. 2022 Apr 18;14(8):1673. doi: 10.3390/nu14081673. [PubMed:35458235 ]
LOTUS database [Link]

Showing NP-Card for (-)-friedelin (NP0170040)

MOL for NP0170040 ((-)-friedelin)

3D MOL for NP0170040 ((-)-friedelin)

3D SDF for NP0170040 ((-)-friedelin)

3D-SDF for NP0170040 ((-)-friedelin)

PDB for NP0170040 ((-)-friedelin)

3D PDB for NP0170040 ((-)-friedelin)

SMILES for NP0170040 ((-)-friedelin)

INCHI for NP0170040 ((-)-friedelin)

Structure for NP0170040 ((-)-friedelin)

3D Structure for NP0170040 ((-)-friedelin)