NP-MRD: Showing NP-Card for 3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid (NP0240224)

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Record Information

Version

2.0

Created at

2022-09-06 23:59:34 UTC

Updated at

2022-09-06 23:59:34 UTC

NP-MRD ID

NP0240224

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

Description

(1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1. 3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid is found in Acer truncatum, Ageratina adenophora, Andrographis paniculata, Anethum graveolens, Antonia ovata, Sorbus aria, Artemisia armeniaca, Artemisia capillaris, Asimina triloba, Aster koraiensis, Aster scaber, Astragalus asper, Astragalus onobrychis, Astragalus saganlugensis, Athyrium filix-femina, Baccharis ochracea, Berberis vulgaris, Brunfelsia grandiflora, Cacalia hastata, Camellia crassicolumna, Camellia oleifera, Campanula glomerata, Caragana spinosa, Carallia brachiata, Castanopsis fissa, Centaurea cyanus, Centaurea deflexa, Centaurea jacea, Centaurea pseudoscabiosa, Centella asiatica, Cephalaria gigantea, Chaerophyllum hirsutum, Chimarrhis turbinata, Tanacetum coccineum, Chrysanthemum morifolium, Leucanthemum vulgare, Cichorium glandulosum, Corchorus olitorius, Coriandrum sativum, Cota altissima, Cotoneaster simonsii, Crataegus viridis, Cussonia arborea, Cyclocarya paliurus, Cydonia oblonga, Cymbopogon citratus, Vincetoxicum hirundinaria, Dactylis glomerata, Duhaldea cappa, Echinacea pallida, Eleutherococcus senticosus, Epimedium sagittatum, Eremochloa ophiuroides, Erigeron canadensis, Eriobotrya japonica, Eucalyptus cypellocarpa, Eucalyptus globulus, Eucommia ulmoides, Euonymus alatus, Eupatorium perfoliatum, Euphorbia tirucalli, Ferula elaeochytris, Forsythia europaea, Galium verum, Glehnia littoralis, Glycine max, Hamamelis virginiana, Hedeoma drummondii, Sorbus thuringiaca, Helichrysum italicum, Helichrysum stoechas, Hieracium gymnocephalum, Hydrangea macrophylla, Hypericum aucheri, Hypericum japonicum, Hypericum perforatum, Hypericum sikokumontanum, Ilex paraguariensis, Ipomoea batatas, Ipomoea nil, Isodon japonicus, Kandelia candel, Lactuca indica, Lamium album, Laserpitium latifolium, Lasthenia californica, Leontopodium alpinum, Lonicera bournei, Loropetalum chinense, Marrubium velutinum, Matteuccia struthiopteris, Molineria capitulata, Morus nigra, Myosotis krylovii, Oenothera speciosa, Onobrychis viciifolia, Ophiorrhiza liukiuensis, Ophiorrhiza pumila, Origanum vulgare, Panzerina lanata, Paronychia kapela, Pelargonium incrassatum, Petasites japonicus, Peucedanum japonicum, Phacelia campanularia, Plantago bellardii, Plantago depressa, Plantago major, Potentilla erecta, Prunus cerasus, Prunus domestica, Prunus padus, Pteridium esculentum, Pyrus calleryana, Reseda muricata, Sida hermaphrodita, Salvia fruticosa, Sambucus ebulus, Sargentodoxa cuneata, Sinoadina racemosa, Smallanthus sonchifolius, Solanum incanum, Solanum lycocarpum, Solanum melongena, Solanum neorickii, Solanum nigrum, Solidago canadensis, Sorbaria sorbifolia, Sorbus tianschanica, Sorbus torminalis, Spinacia oleracea, Spondias mombin, Stachys byzantina, Stenostomum acreanum, Symphytum officinale, Tanacetum balsamita, Trachelospermum jasminoides, Trifolium alpestre, Tropaeolum majus, Uncaria hirsuta, Vaccinium arctostaphylos, Vaccinium dunalianum, Vaccinium myrtillus, Valeriana amurensis, Valeriana prionophylla, Viburnum dilatatum, Vigna radiata, Vinca major, Viscum album, Werneria nubigena, Xanthium strumarium, Youngia japonica and Zanthoxylum piperitum. Based on a literature review very few articles have been published on (1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072201592D          

 25 26  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 O   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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    0.6817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946    1.7435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2481    2.2322    0.0000 O   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
    1.4289    0.8250    0.0000 C   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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.5601   -1.7413    1.8591 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1619   -1.0133    1.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6126   -1.1945    1.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3140   -0.4110    0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7499   -0.5014    0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4622   -1.4277    0.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8508   -1.4874    0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4840   -0.6204   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8684   -0.7369   -0.2703 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7807    0.3299   -0.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4486    1.1953   -1.7578 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4098    0.3579   -0.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946   -0.0489    0.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8956    0.0842    0.4523 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5195   -0.0142   -0.9138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0008   -0.1677   -0.7052 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6101    0.1882   -1.9391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3403   -1.5990   -0.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0398   -2.2116   -1.2875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118   -2.2718    0.7009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5235    0.6848    0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6613    1.8155    0.8323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8050    2.9216   -0.0001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2043    1.4794    0.9526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7329    1.5494    2.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694   -1.9440    1.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7939    0.3667   -0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0104   -2.1388    1.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4188   -2.2152    1.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3378   -0.1008   -0.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8797    1.8626   -2.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8416    1.1017   -1.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3595   -0.6186    1.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3733    0.9705   -1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0958   -0.8468   -1.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4142   -0.5730   -2.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3583   -2.1962    1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8059    0.0312    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4936    1.1256    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0080    2.1303    1.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7207    3.2954    0.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.1656    0.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9899    2.4246    2.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 21  1  0
 21 16  1  0
 16 17  1  6
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13  2  1  0
  2  1  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
 14 24  1  0
 24 25  1  0
 16 18  1  0
 18 20  1  0
 18 19  2  0
 24 22  1  0
 12  5  1  0
 23 41  1  0
 22 40  1  1
 21 38  1  0
 21 39  1  0
 17 36  1  0
 15 34  1  0
 15 35  1  0
 14 33  1  1
  3 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 24 42  1  6
 25 43  1  0
 20 37  1  0
M  END


  Mrv1652309072201592D          

 25 26  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 O   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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    0.6817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946    1.7435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2481    2.2322    0.0000 O   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
    1.4289    0.8250    0.0000 C   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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0240224

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC(O)(CC(OC(=O)C=CC2=CC=C(O)C(O)=C2)C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)

> <INCHI_KEY>
CWVRJTMFETXNAD-UHFFFAOYSA-N

> <FORMULA>
C16H18O9

> <MOLECULAR_WEIGHT>
354.311

> <EXACT_MASS>
354.09508216

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.30700698134429

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

> <JCHEM_LOGP>
-0.26852975799999984

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.20854914523281

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3338531471838464

> <JCHEM_PKA_STRONGEST_BASIC>
-3.231823980915407

> <JCHEM_POLAR_SURFACE_AREA>
164.75

> <JCHEM_REFRACTIVITY>
83.23470000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   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       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.517   1.273   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.527   2.987   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.043   3.255   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.463   4.167   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   21                                             
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   14   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
(1S,3R,4R,5R)-3-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylate	Generator
3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate	HMDB

Chemical Formula

C₁₆H₁₈O₉

Average Mass

354.3110 Da

Monoisotopic Mass

354.09508 Da

IUPAC Name

3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

Traditional Name

3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC1CC(O)(CC(OC(=O)C=CC2=CC=C(O)C(O)=C2)C1O)C(O)=O

InChI Identifier

InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)

InChI Key

CWVRJTMFETXNAD-UHFFFAOYSA-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 truncatum	LOTUS Database	35616633
Ageratina adenophora	LOTUS Database	35616633
Andrographis paniculata	LOTUS Database	35616633
Anethum graveolens	LOTUS Database	35616633
Antonia ovata	LOTUS Database	35616633
Aria edulis	LOTUS Database	35616633
Artemisia armeniaca	LOTUS Database	35616633
Artemisia capillaris	LOTUS Database	35616633
Asimina triloba	LOTUS Database	35616633
Aster koraiensis	LOTUS Database	35616633
Aster scaber	LOTUS Database	35616633
Astragalus asper	LOTUS Database	35616633
Astragalus onobrychis	LOTUS Database	35616633
Astragalus saganlugensis	LOTUS Database	35616633
Athyrium filix-femina	LOTUS Database	35616633
Baccharis ochracea	LOTUS Database	35616633
Berberis vulgaris	LOTUS Database	35616633
Brunfelsia grandiflora	LOTUS Database	35616633
Cacalia hastata	LOTUS Database	35616633
Camellia crassicolumna	LOTUS Database	35616633
Camellia oleifera	LOTUS Database	35616633
Campanula glomerata	LOTUS Database	35616633
Caragana spinosa	LOTUS Database	35616633
Carallia brachiata	LOTUS Database	35616633
Castanopsis fissa	LOTUS Database	35616633
Centaurea cyanus	LOTUS Database	35616633
Centaurea deflexa	LOTUS Database	35616633
Centaurea jacea	LOTUS Database	35616633
Centaurea pseudoscabiosa	LOTUS Database	35616633
Centella asiatica	LOTUS Database	35616633
Cephalaria gigantea	LOTUS Database	35616633
Chaerophyllum hirsutum	LOTUS Database	35616633
Chimarrhis turbinata	LOTUS Database	35616633
Chrysanthemum coccineum	LOTUS Database	35616633
Chrysanthemum morifolium	LOTUS Database	35616633
Chrysanthemum vulgare	LOTUS Database	35616633
Cichorium glandulosum	LOTUS Database	35616633
Corchorus olitorius	LOTUS Database	35616633
Coriandrum sativum	LOTUS Database	35616633
Cota altissima	LOTUS Database	35616633
Cotoneaster simonsii	LOTUS Database	35616633
Crataegus viridis	LOTUS Database	35616633
Cussonia arborea	LOTUS Database	35616633
Cyclocarya paliurus	LOTUS Database	35616633
Cydonia oblonga	LOTUS Database	35616633
Cymbopogon citratus	LOTUS Database	35616633
Cynanchum vincetoxicum	LOTUS Database	35616633
Dactylis glomerata	LOTUS Database	35616633
Duhaldea cappa	LOTUS Database	35616633
Echinacea pallida	LOTUS Database	35616633
Eleutherococcus senticosus	LOTUS Database	35616633
Epimedium sagittatum	LOTUS Database	35616633
Eremochloa ophiuroides	LOTUS Database	35616633
Erigeron canadensis	LOTUS Database	35616633
Eriobotrya japonica	LOTUS Database	35616633
Eucalyptus cypellocarpa	LOTUS Database	35616633
Eucalyptus globulus	LOTUS Database	35616633
Eucommia ulmoides	LOTUS Database	35616633
Euonymus alatus	LOTUS Database	35616633
Eupatorium perfoliatum	LOTUS Database	35616633
Euphorbia tirucalli	LOTUS Database	35616633
Ferula elaeochytris	LOTUS Database	35616633
Forsythia europaea	LOTUS Database	35616633
Galium verum	LOTUS Database	35616633
Glehnia littoralis	LOTUS Database	35616633
Glycine max	LOTUS Database	35616633
Hamamelis virginiana	LOTUS Database	35616633
Hedeoma drummondii	LOTUS Database	35616633
Hedlundia x thuringiaca	LOTUS Database	35616633
Helichrysum italicum	LOTUS Database	35616633
Helichrysum stoechas	LOTUS Database	35616633
Hieracium gymnocephalum	LOTUS Database	35616633
Hydrangea macrophylla	LOTUS Database	35616633
Hypericum aucheri	LOTUS Database	35616633
Hypericum japonicum	LOTUS Database	35616633
Hypericum perforatum	LOTUS Database	35616633
Hypericum sikokumontanum	LOTUS Database	35616633
Ilex paraguariensis	LOTUS Database	35616633
Ipomoea batatas	LOTUS Database	35616633
Ipomoea nil	LOTUS Database	35616633
Isodon japonicus	LOTUS Database	35616633
Kandelia candel	LOTUS Database	35616633
Lactuca indica	LOTUS Database	35616633
Lamium album	LOTUS Database	35616633
Laserpitium latifolium	LOTUS Database	35616633
Lasthenia californica	LOTUS Database	35616633
Leontopodium alpinum	LOTUS Database	35616633
Lonicera bournei Hemsl.	LOTUS Database	35616633
Loropetalum chinense	LOTUS Database	35616633
Marrubium velutinum	LOTUS Database	35616633
Matteuccia struthiopteris	LOTUS Database	35616633
Molineria capitulata	LOTUS Database	35616633
Morus nigra	LOTUS Database	35616633
Myosotis krylovii	LOTUS Database	35616633
Oenothera speciosa	LOTUS Database	35616633
Onobrychis viciifolia	LOTUS Database	35616633
Ophiorrhiza liukiuensis	LOTUS Database	35616633
Ophiorrhiza pumila	LOTUS Database	35616633
Origanum vulgare	LOTUS Database	35616633
Panzerina lanata	LOTUS Database	35616633
Paronychia kapela	LOTUS Database	35616633
Pelargonium incrassatum	LOTUS Database	35616633
Petasites japonicus	LOTUS Database	35616633
Peucedanum japonicum	LOTUS Database	35616633
Phacelia campanularia	LOTUS Database	35616633
Plantago bellardii	LOTUS Database	35616633
Plantago depressa	LOTUS Database	35616633
Plantago major	LOTUS Database	35616633
Potentilla erecta	LOTUS Database	35616633
Prunus cerasus	LOTUS Database	35616633
Prunus domestica	LOTUS Database	35616633
Prunus padus	LOTUS Database	35616633
Pteridium esculentum	LOTUS Database	35616633
Pyrus kawakamii	LOTUS Database	35616633
Reseda muricata	LOTUS Database	35616633
Ripariosida hermaphrodita	LOTUS Database	35616633
Salvia fruticosa	LOTUS Database	35616633
Sambucus ebulus	LOTUS Database	35616633
Sargentodoxa cuneata	LOTUS Database	35616633
Sinoadina racemosa	LOTUS Database	35616633
Smallanthus sonchifolius	LOTUS Database	35616633
Solanum incanum	LOTUS Database	35616633
Solanum lycocarpum	LOTUS Database	35616633
Solanum melongena	LOTUS Database	35616633
Solanum neorickii	LOTUS Database	35616633
Solanum nigrum	LOTUS Database	35616633
Solidago canadensis	LOTUS Database	35616633
Sorbaria sorbifolia	LOTUS Database	35616633
Sorbus tianschanica	LOTUS Database	35616633
Sorbus torminalis	LOTUS Database	35616633
Spinacia oleracea	LOTUS Database	35616633
Spondias mombin	LOTUS Database	35616633
Stachys byzantina	LOTUS Database	35616633
Stenostomum acreanum	LOTUS Database	35616633
Symphytum officinale	LOTUS Database	35616633
Tanacetum balsamita	LOTUS Database	35616633
Trachelospermum jasminoides	LOTUS Database	35616633
Trifolium alpestre	LOTUS Database	35616633
Tropaeolum majus	LOTUS Database	35616633
Uncaria hirsuta	LOTUS Database	35616633
Vaccinium arctostaphylos	LOTUS Database	35616633
Vaccinium dunalianum	LOTUS Database	35616633
Vaccinium myrtillus	LOTUS Database	35616633
Valeriana amurensis	LOTUS Database	35616633
Valeriana prionophylla	LOTUS Database	35616633
Viburnum dilatatum	LOTUS Database	35616633
Vigna radiata	LOTUS Database	35616633
Vinca major	LOTUS Database	35616633
Viscum album	LOTUS Database	35616633
Werneria nubigena	LOTUS Database	35616633
Xanthium strumarium	LOTUS Database	35616633
Youngia japonica	LOTUS Database	35616633
Zanthoxylum piperitum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Fatty acid ester
Phenol
Fatty acyl
Hydroxy acid
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha-hydroxy acid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	-0.27	ChemAxon
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.23 m³·mol⁻¹	ChemAxon
Polarizability	33.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0242450

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

308990

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

348159

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid (NP0240224)

MOL for NP0240224 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid)

3D MOL for NP0240224 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid)

3D SDF for NP0240224 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid)

3D-SDF for NP0240224 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid)

PDB for NP0240224 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid)

3D PDB for NP0240224 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid)

SMILES for NP0240224 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid)

INCHI for NP0240224 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid)

Structure for NP0240224 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid)

3D Structure for NP0240224 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid)