Dicaffeic acid






Names

    • J-003723
    • AKOS015912727
    • 30964-13-7
    • (1R,3R,4S,5R)-1,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxycyclohexane-1-carboxylic acid
    • CHEBI:520
    • Q1763092
    • SCHEMBL42528
    • Cyclohexanecarboxylic acid,1,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-4,5-dihydroxy-,(1R,3R,4S,5R)-
    • DTXSID0050423
    • Cyclohexanecarboxylic acid, 1,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-4,5-dihydroxy-
    • Cynaricine
    • Cynarine [INN:WHO-DD]
    • 212891-05-9
    • HY-N0359R
    • Cynarin (Standard)
    • (1R,3R,4S,5R)-1,3-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexanecarboxylic acid
    • BCP29379
    • 1,5-DQA
    • 85D81U9JAV
    • Cynarin
    • DA-52251
    • Dicaffeic acid
    • CHEMBL487258
    • Chinasaeure-1,3-dikaffeesaeureester
    • DTXSID301309674
    • Cynarine
    • s3301
    • Cynarine [MART.]
    • Cynarin (1,3-Dicaffeoylquinic acid)
    • (1R,3R,4S,5R)-1,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-4,5-dihydroxycyclohexanecarboxylic acid
    • CS-6280
    • 1884-23-7
    • (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
    • 1,5-Dicaffeoyl quinic acid
    • MFCD11112054
    • 1-O,3-O-Bis(3,4-dihydroxycinnamoyl)chinasaeure
    • Phemocil
    • Q-100389
    • AS-74959
    • (1R-(1alpha,3alpha,4alpha,5beta))-1,3-Bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-4,5-dihydroxycyclohexanecarboxylic acid
    • AC-6022
    • Caffeic acid 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene ester
    • Listrocol
    • NS00007039
    • 1,5-di-O-Caffeoylquinic acid
    • NCGC00274085-01
    • Cynarine [MI]
    • (1R,3R,4S,5R)-1,3-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexanecarboxylicacid
    • UNII-85D81U9JAV
    • (1R,3R,4S,5R)-1,3-Bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-4,5-dihydroxycyclohexanecarboxylic acid
    • Cynarine (MART.)
    • DTXCID9029805
    • 1,3-Dicqa
    • (1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
    • Cinarin
    • HY-N0359
    • Cynarine;1,3-Dicaffeoylquinic acid;1,5-DQA;1,5-Dicaffeoylquinic acid
    • cynarinum
    • 1,3-Dicaffeoylquinic acid (constituent of echinacea angustifolia root, echinacea pallida root, echinacea purpurea root and echinacea purpurea aerial parts)
    • 3,4-Dihydroxycinnamic acid 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene ester
    • (1R,3R,4S,5R)-1,3-bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexane-1-carboxylic acid
    • Tox21_111176
    • Quinic acid 1,5-dicaffeic ester
    • 1_5_dihydrocaffeoylquinic_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)-
    • CAS-30964-13-7
    • 1,5-Dicaffeoylqunic acid
    • Plemocil
    • DA-49032
    • Cinarine
    • (1R,3R,4S,5R)-1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid
    • Tox21_111176_1
    • 1,3-Dicaffeoylquinic acid, >=98% (HPLC)
    • YDDUMTOHNYZQPO-RVXRWRFUSA-N
    • 3,4-Dihydroxycinnamic acid, 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene ester
    • Cynarine [WHO-DD]
    • BDBM50369484
    • 1,5-Dicaffeoylquinic acid
    • 1-carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate)
    • Cynarine [INN]
    • Cynarin, analytical standard
    • 1,3-Dicaffeoylquinic acid

Attributes

  • Canonical 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

  • 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

  • Molecule Class: Flavonoids
  • TPSA: 211.27999999999997
  • #RotBonds: 7
  • MW: 516.4550000000002
  • HBD: 7
  • HBA: 11
  • logP: 1.0295999999999994
  • Chemical Formula: C25H24O12


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. heyneana India 2563820 -

External Databases


References

  • Simultaneous Extraction Optimization and Analysis of Flavonoids from the Flowers of Tabernaemontana heyneana by High Performance Liquid Chromatography Coupled to Diode Array Detector and Electron Spray Ionization/Mass Spectrometry. ISRN Biotechnol, 2013 (PMID 25969771).

Compound-Protein Relationships

Compound Activities

    • Antithrombogenic
    • Antiviral
    • Antimicrobial
    • Antioxidant
    • Antihypercholesterolemic

Predicted NMR Spectral Data


Predicted MS Fragmentation Pattern

    N.B.: It is recommended to zoom in on a specific area of an MS plot before hovering on a peak.


Predicted ADMET Properties

    Property Model Name Predicted Value

    Absorption Caco-2 (logPaap) -6.78
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.13
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.18

    Distribution Blood-Brain Barrier (Central Nervous System) -2.95
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.9
    Plasma Protein Binding 88.97
    Steady State Volume of Distribution 0.65

    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Non-Substrate
    OATP1B1 Inhibitor
    OATP1B3 Non-Inhibitor

    Excretion Clearance 9.86
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life >= 3hs

    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Safe
    Bioconcentration Factor -1.88
    Biodegradation Toxic
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 0.72
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.02
    Micronucleos Toxic
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Safe
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis -469.53
    Rat (Acute) 2.18
    Rat (Chronic Oral) 3.49
    Fathead Minnow 3.91
    Respiratory Disease Safe
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe

    General Properties Boiling Point 578.4
    Hydration Free Energy -3.07
    Log(D) at pH=7.4 0.14
    Log(P) 1.19
    Log S -2.69
    Log(Vapor Pressure) -14.65
    Melting Point 231.95
    pKa Acid 5.27
    pKa Basic 5.51