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Chicoric Acid

PubChem CID: 5281764

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Compound Synonyms Chicoric acid, Cichoric Acid, L-Chicoric acid, 70831-56-0, 6537-80-0, (-)-Chicoric acid, dicaffeoyltartaric acid, (2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid, (-)-L-Chicoric acid, NSC 699173, Chicoric acid, (-)-, L-Cichoric acid, S4YY3V8YHD, L-DCTA, NSC699173, Dicaffeoyl-L-tartaric acid, trans-Caffeoyltartaric acid, NSC-699173, 2,3-Bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)butanedioic acid, (R-(R*,R*-(E,E)))-2,3-Bis((3-(3,4-dihydroxphenyl)-1-oxo-2-propenyl)oxy)butanedioic acid, CHEBI:3594, CHEMBL282731, CHICORIC ACID [USP-RS], DTXSID0033332, (2R,3R)-2,3-bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)succinic acid, NSC-99173, (2R,3R)-2,3-Bis[[(E)-3-(3,4-dihydroxyphenyl)acryloyl]oxy]succinic Acid, Butanedioic acid, 2,3-bis(((2E)-3-(3,4-dihydroxphenyl)-1-oxo-2-propenyl)oxy)-, (2R,3R)-, Butanedioic acid, 2,3-bis((3-(3,4-dihydroxphenyl)-1-oxo-2-propenyl)oxy)-, (R-(R*,R*-(E,E)))-, TARTARIC ACID, BIS(3,4-DIHYDROXYCINNAMATE), CHICORIC ACID (USP-RS), (2R,3R)-2,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid, Butanedioic acid, 2,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (R-(R*,R*))-, Butanedioic acid, 2,3-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (2R,3R)-, butanedioic acid, 2,3-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-, (2R,3R)-, UNII-S4YY3V8YHD, L-Chicoricacid, 1-chicoricacid, Cichoric-Acid, l-Chicoric-acid, (2R,3R)-2,3-bis(((E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy)butanedioic acid, GKP, (-)-Chicoric acid, trans-Caffeoyltartaric acid, L-CA, (-)-CICHORIC ACID, 2,3-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid, DTXCID8013332, SCHEMBL15532218, 2,3-Dicaffeoyl-L-tartaric acid, (2S,3S)-2,3-bis((((2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy))butanedioic acid, (2S,3S)-2,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioic acid, YDDGKXBLOXEEMN-IABMMNSOSA-N, GLXC-10979, Chicoric Acid, >=95% (HPLC), HY-N0457, Tox21_201055, BDBM50076273, MFCD00189418, s9133, AKOS000278435, CCG-269487, CS-4262, FC65730, (2R,3R)-2,3-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-butanedioic acid, ( -)-Chicoric acid, analytical standard, NCGC00091914-01, NCGC00091914-02, NCGC00091914-04, NCGC00258608-01, 1ST40121, AC-34315, AC-36990, AS-56447, DA-72145, DA-72146, CAS-70831-56-0, C3450, NS00037116, D78144, Q5119402, Chicoric Acid, United States Pharmacopeia (USP) Reference Standard, (2R,3R)-2,3-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)succinic acid, (2R,3R)-2,3-bis((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)succinic acid, (2R,3R)-2,3-Bis-[(E)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-succinic acid, (2R,3R)-2,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}succinic acid, (2R,3R)-2,3-bis{[3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid, [S-(R*,R*)]-2,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]butanedioic acid, 636-229-3, Butanedioic acid, 2,3-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (2R,3R)- (9CI), Butanedioic acid, 2,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, [R-[R*,R*-(E,E)]]-, CHICORIC ACID (CONSTITUENT OF ECHINACEA ANGUSTIFOLIA ROOT, ECHINACEA PALLIDA ROOT, ECHINACEA PURPUREA ROOT AND ECHINACEA PURPUREA AERIAL PARTS), NCGC00091914-04!(2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
Ghose Rule True
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 208.0
Hydrogen Bond Donor Count 6.0
Pfizer 3 75 Rule True
Scaffold Graph Level CC(CCCCC(C)CCC1CCCCC1)CCC1CCCCC1
Np Classifier Class Cinnamic acids and derivatives
Deep Smiles O=CO[C@H][C@H]C=O)O))OC=O)/C=C/cccccc6)O))O))))))))))C=O)O))))/C=C/cccccc6)O))O
Heavy Atom Count 34.0
Classyfire Class Carboxylic acids and derivatives
Scaffold Graph Node Level OC(CCC1CCCCC1)OCCOC(O)CCC1CCCCC1
Classyfire Subclass Tetracarboxylic acids and derivatives
Isotope Atom Count 0.0
Molecular Complexity 740.0
Database Name cmaup_ingredients;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 2.0
Uniprot Id Q7ZJM1, P06239, P12931, P42224, P40763, P51692, Q99714, Q9NUW8, P16050, P15917, P04637, Q13951, P10145, P51449, P27695, P0DTD1, n.a., P15273, Q16236
Iupac Name (2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
Prediction Hob 0.0
Class Carboxylic acids and derivatives
Veber Rule False
Classyfire Superclass Organic acids and derivatives
Target Id NPT149, NPT50, NPT792, NPT539
Xlogp 2.0
Superclass Organic acids and derivatives
Subclass Tetracarboxylic acids and derivatives
Gsk 4 400 Rule False
Molecular Formula C22H18O12
Scaffold Graph Node Bond Level O=C(C=Cc1ccccc1)OCCOC(=O)C=Cc1ccccc1
Prediction Swissadme 0.0
Inchi Key YDDGKXBLOXEEMN-IABMMNSOSA-N
Silicos It Class Soluble
Fcsp3 0.0909090909090909
Logs -3.503
Rotatable Bond Count 11.0
State Solid
Logd 3.427
Synonyms Chicate, Chicic acid, L-Chicoric acid, (-)-L-Chicoric acid, 2,3-Bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)butanedioic acid, (-)-Chicoric acid, Cichoric acid, Dicaffeoyltartaric acid, L-Chicate, L-Chicic acid, CICHate, CICHic acid, (2R,3R)-2,3-Bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioate, (2R,3R)-2,3-Bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]butanedioic acid, (2R,3R)-2,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]butanedioic acid, trans-Caffeoyltartaric acid, (2R,3R)-2,3-Bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-butanedioic acid, Chicoric acid, chicoric acid, chicoric-acid, cichoric acid, cichoric-acid
Esol Class Soluble
Functional Groups CC(=O)O, c/C=C/C(=O)OC, cO
Compound Name Chicoric Acid
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 474.08
Formal Charge 0.0
Monoisotopic Mass 474.08
Hydrogen Bond Acceptor Count 12.0
Molecular Weight 474.4
Gi Absorption False
Covalent Unit Count 1.0
Total Atom Stereocenter Count 2.0
Total Bond Stereocenter Count 2.0
Molecular Framework Aromatic homomonocyclic compounds
Lipinski Rule Of 5 True
Esol -3.5825952705882362
Inchi InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1
Smiles C1=CC(=C(C=C1/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC(=C(C=C2)O)O)C(=O)O)O)O
Nring 2.0
Np Classifier Biosynthetic Pathway Shikimates and Phenylpropanoids
Defined Bond Stereocenter Count 2.0
Egan Rule False
Taxonomy Direct Parent Tetracarboxylic acids and derivatives
Np Classifier Superclass Phenylpropanoids (C6-C3)

  • 1. Outgoing r'ship FOUND_IN to/from Agathosma Scaberula (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 2. Outgoing r'ship FOUND_IN to/from Balanophora Harlandii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 3. Outgoing r'ship FOUND_IN to/from Cichorium Endivia (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/16076140
  • 4. Outgoing r'ship FOUND_IN to/from Cichorium Glandulosum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 5. Outgoing r'ship FOUND_IN to/from Cichorium Intybus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 6. Outgoing r'ship FOUND_IN to/from Echinacea Angustifolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 7. Outgoing r'ship FOUND_IN to/from Echinacea Purpurea (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 8. Outgoing r'ship FOUND_IN to/from Equisetum Arvense (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/12875242
  • 9. Outgoing r'ship FOUND_IN to/from Euphorbia Biglandulosa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 10. Outgoing r'ship FOUND_IN to/from Isodon Rubescens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 11. Outgoing r'ship FOUND_IN to/from Lupinus Cosentinii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 12. Outgoing r'ship FOUND_IN to/from Ocimum Basilicum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 13. Outgoing r'ship FOUND_IN to/from Ocimum Gratissimum (Plant) Rel Props:Source_db:cmaup_ingredients
  • 14. Outgoing r'ship FOUND_IN to/from Polemonium Caeruleum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 15. Outgoing r'ship FOUND_IN to/from Pteridium Aquilinum (Plant) Rel Props:Reference:https://doi.org/10.15482/usda.adc/1239279
  • 16. Outgoing r'ship FOUND_IN to/from Strychnos Ledermannii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 17. Outgoing r'ship FOUND_IN to/from Taraxacum Borealisinense (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 18. Outgoing r'ship FOUND_IN to/from Taraxacum Coreanum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 19. Outgoing r'ship FOUND_IN to/from Taraxacum Mongolicum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 20. Outgoing r'ship FOUND_IN to/from Taraxacum Officinale (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 21. Outgoing r'ship FOUND_IN to/from Taraxacum Platycarpum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 22. Outgoing r'ship FOUND_IN to/from Viburnum Davidii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 23. Outgoing r'ship FOUND_IN to/from Youngia Japonica (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/19571418
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