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Cynarine

PubChem CID: 5281769

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Compound Synonyms Cynarin, Cynarine, 30964-13-7, Cinarine, Cinarin, 1,5-Dicaffeoylquinic acid, Plemocil, 1,3-Dicaffeoylquinic acid, Cynarine [INN], 212891-05-9, Listrocol, 1,3-Dicqa, 1,5-Dicaffeoylqunic acid, UNII-85D81U9JAV, Cynarine [MI], 85D81U9JAV, Cynarine [MART.], Cynarine [WHO-DD], Quinic acid 1,5-dicaffeic ester, (1R,3R,4S,5R)-1,3-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexanecarboxylic acid, CHEBI:520, 1,5-di-O-Caffeoylquinic acid, Caffeic acid 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene ester, 1-carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate), Cynarine (MART.), (1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid, Cyclohexanecarboxylic acid,1,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-4,5-dihydroxy-,(1R,3R,4S,5R)-, 3,4-Dihydroxycinnamic acid 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene ester, 3,4-Dihydroxycinnamic acid, 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene ester, (1R,3R,4S,5R)-1,3-Bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-4,5-dihydroxycyclohexanecarboxylic acid, Cyclohexanecarboxylic acid, 1,3-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-4,5-dihydroxy-, (1R,3R,4S,5R)-, 1884-23-7, DTXCID9029805, 1,5-DQA, Phemocil, (1R,3R,4S,5R)-1,3-bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexane-1-carboxylic acid, (1R,3R,4S,5R)-1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid, (1R,3R,4S,5R)-1,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-4,5-dihydroxycyclohexanecarboxylic acid, (1R-(1alpha,3alpha,4alpha,5beta))-1,3-Bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-4,5-dihydroxycyclohexanecarboxylic acid, Cyclohexanecarboxylic acid, 1,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-4,5-dihydroxy-, CAS-30964-13-7, DTXSID0050423, cynarinum, Cynaricine, Chinasaeure-1,3-dikaffeesaeureester, Cynarin (Standard), MFCD11112054, 1-O,3-O-Bis(3,4-dihydroxycinnamoyl)chinasaeure, Cynarine [INN:WHO-DD], Cynarin, analytical standard, 1,5-Dicaffeoyl quinic acid, SCHEMBL42528, 1_5_dihydrocaffeoylquinic_acid, CHEMBL487258, HY-N0359R, YDDUMTOHNYZQPO-RVXRWRFUSA-N, DTXSID301309674, BCP29379, HY-N0359, Tox21_111176, BDBM50369484, s3301, Cynarin (1,3-Dicaffeoylquinic acid), AKOS015912727, Tox21_111176_1, AC-6022, CS-6280, NCGC00274085-01, AS-74959, DA-49032, DA-52251, FD157793, FD157794, NS00007039, 1,3-Dicaffeoylquinic acid, >=98% (HPLC), Q1763092, Cynarine, 1,3-Dicaffeoylquinic acid, 1,5-DQA, 1,5-Dicaffeoylquinic acid, (1R,3R,4S,5R)-1,3-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexanecarboxylicacid, (1R,3R,4S,5R)-1,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxycyclohexane-1-carboxylic acid, (1R-(1.ALPHA.,3.ALPHA.,4.ALPHA.,5.BETA.))-1,3-BIS((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-4,5-DIHYDROXYCYCLOHEXANECARBOXYLIC ACID, 1,3-Dicaffeoylquinic acid (constituent of echinacea angustifolia root, echinacea pallida root, echinacea purpurea root and echinacea purpurea aerial parts), Cinarine, (1R,3R,4S,5R)-1,3-bis[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-4,5-dihydroxy-cyclohexanecarboxylic acid
Topological Polar Surface Area 211.0
Hydrogen Bond Donor Count 7.0
Heavy Atom Count 37.0
Description Cynarine is a hydroxycinnamic acid and a biologically active chemical constituent of artichoke. Chemically, it is an ester formed from quinic acid and two units of caffeic acid. 1,5-Dicaffeoylquinic acid is found in cardoon, globe artichoke, and fennel.
Isotope Atom Count 0.0
Molecular Complexity 887.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;npass_chem_all;pubchem
Defined Atom Stereocenter Count 4.0
Uniprot Id Q7ZJM1, P24298, P06239, P12931, P42224, P40763, P51692, P11344, n.a.
Iupac Name (1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
Prediction Hob 0.0
Class Alcohols and polyols
Xlogp 1.5
Superclass Organooxygen compounds
Subclass Cyclic alcohols and derivatives
Molecular Formula C25H24O12
Prediction Swissadme 0.0
Inchi Key YDDUMTOHNYZQPO-RVXRWRFUSA-N
Fcsp3 0.24
Logs -2.03
Rotatable Bond Count 9.0
Logd 0.345
Synonyms 1,5-Di-O-caffeoylquinic acid, Cinarine, Cynarin, Cynarine, 1,5-Dicaffeoylquinate, 1,3-Dicaffeoylquinate, Cinarin, Cynarix, Listrocol, Phemocil, 1,5-Dicaffeoylquinic acid, Nivellipid, Cinarina, Cynarin, (1alpha,3alpha,4alpha,5beta)-isomer, 1-Carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate), Cynarex, Listricol
Substituent Name Quinic acid, Cinnamic acid ester, Hydroxycinnamic acid or derivatives, Coumaric acid or derivatives, Cinnamic acid or derivatives, Tricarboxylic acid or derivatives, Phenylpropene, Styrene, 1,2-diphenol, Phenol, Fatty acid ester, Cyclohexanol, Fatty acyl, Benzenoid, Monocyclic benzene moiety, Alpha,beta-unsaturated carboxylic ester, Enoate ester, Secondary alcohol, Carboxylic acid ester, 1,2-diol, Ether, Carboxylic acid, Carboxylic acid derivative, Hydrocarbon derivative, Carbonyl group, Aromatic homomonocyclic compound
Compound Name Cynarine
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 516.127
Formal Charge 0.0
Monoisotopic Mass 516.127
Hydrogen Bond Acceptor Count 12.0
Molecular Weight 516.4
Covalent Unit Count 1.0
Total Atom Stereocenter Count 4.0
Total Bond Stereocenter Count 2.0
Molecular Framework Aromatic homomonocyclic compounds
Esol -3.645621000000002
Inchi InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
Smiles C1[C@H]([C@@H]([C@@H](C[C@]1(C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)O)O
Nring 3.0
Defined Bond Stereocenter Count 2.0
Taxonomy Direct Parent Quinic acids and derivatives

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