Caffeic acid






Names

    • CAFFEIC ACID (CONSTITUENT OF BLACK COHOSH)
    • CHEMBL145
    • 2-Propenoic acid,3-(3,4-dihydroxyphenyl)-, (2E)-
    • CCRIS 847
    • HSDB 7088
    • Z240113804', "2',3-DIHYDROXY-4,4',6'-TRIMETHOXYCHALCONE_met021", "2',4-DIHYDROXY-3,4',6'-TRIMETHOXYCHALCONE_met023", '8B3E4DA7-F3B0-4972-A315-2E387071737F
    • trans-3,4-Dihydroxycinnamic Acid
    • SPECTRUM1503987
    • 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-
    • DTXSID5020231
    • AC-8006
    • MLS000069738
    • CAFFEIC ACID natural
    • NCGC00017364-10
    • EU-0100208
    • 331-89-5
    • Caffeic acid - Natural
    • SR-01000000203-8
    • 331-39-5
    • caffeic-acid
    • NCGC00017364-11
    • NSC-623438
    • Q414116
    • NCGC00017364-22
    • trans-Caffeate
    • CAFFEIC ACID (CONSTITUENT OF BLACK COHOSH) [DSC]
    • SCHEMBL23358
    • CAFFEIC ACID [IARC]
    • 3,4-Dihydroxycinnamic acid, predominantly trans
    • MLS002207132
    • cid_689043
    • InChI=1/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2
    • 3,4-Dihydroxycinnamic acid
    • AI3-63211
    • C 0625
    • NCGC00260893-01
    • Cinnamic acid, 3,4-dihydroxy-
    • NS00010313
    • trans-Caffeic acid, certified reference material, TraceCERT(R)
    • NCGC00258202-01
    • EINECS 206-361-2
    • (E)-3,4-dihydroxycinnamic acid
    • NCGC00022654-03
    • BRD-K09900591-001-26-7
    • MLS001076493
    • NSC57197
    • Caffeic Acid,(S)
    • caffeic acid
    • STK397812
    • NCGC00022654-09
    • Caffeic acid, matrix substance for MALDI-MS, >=99.0% (HPLC)
    • NCGC00017364-04
    • NCGC00022654-05
    • C-1500
    • CHEBI:16433
    • AR-360/40806927
    • 3-(3,4-Dihydroxyphenyl)propenoic acid
    • NSC623438
    • DB01880
    • NCGC00022654-07
    • BDBM4375
    • Caffeic acid
    • HY-N0172
    • HMS2235G09
    • (E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
    • C01197
    • Tox21_200648
    • SMR004703501
    • Caffeate
    • 3-(3,4-Dihydroxyphenyl)-2-propenoic acid
    • DB-321780
    • Caffeic Acid1507
    • 501-16-6
    • 3-(3,4-dihydroxyphenyl)prop-2-enoic acid
    • CAFFEIC ACID [WHO-DD]
    • 3,4-Dihydroxy-trans-cinnamate
    • Opera_ID_1700
    • NCGC00017364-13
    • NCGC00017364-08
    • 3,4-Dihydroxybenzeneacrylate
    • Trans 3,4-Dihydroxycinnamic acid
    • F3096-1708
    • 3,4-dihydroxycinnamate
    • NCGC00017364-06
    • MFCD00004392
    • HMS3649O17
    • CAS-331-39-5
    • GTPL5155
    • CAFFEIC ACID [MI]
    • (2E)-3-(3,4-dihydroxyphenyl)acrylic acid
    • NCGC00017364-07
    • caffeic acid, (E)-isomer
    • 3,4-Dihydroxybenzeneacrylic acid
    • LP00208
    • NSC-57197
    • Caffeic acid, 1
    • 3-(3,4-dihydroxyphenyl)acrylic acid
    • s2277
    • (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
    • NSC 57197
    • CAFFEIC ACID [HSDB]
    • BP-30112
    • Caffeic acid, United States Pharmacopeia (USP) Reference Standard
    • (2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid
    • Cinnamic acid,4-dihydroxy-
    • AKOS000144463
    • MLS006011849
    • NCGC00017364-09
    • 3,4-Dihydroxycinnamate, XVII
    • Caffeic acid, trans-
    • CS-8205
    • 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, (2E)-
    • MLS002222302
    • NCGC00263641-01
    • SDCCGSBI-0050196.P004
    • CAFFEIC ACID [DSC]
    • 2-Propenoic acid,4-dihydroxyphenyl)-
    • NCGC00022654-04
    • XC164210', "4-(2'Carboxyvinyl)-1,2-dihydroxybenzene", 'Caffeic acid, purum, >=95.0% (HPLC)
    • U2S3A33KVM
    • HY-121231
    • Caffeic acid pure
    • BRD-K09900591-001-25-9
    • EN300-1067793
    • NCGC00022654-08
    • DTXCID10231
    • AS-10895
    • SR-01000000203-7
    • SR-01000000203-6
    • SR-01000000203-2
    • CHEBI:36281
    • BIDD:ER0456
    • (E)-3-(3,4-dihydroxyphenyl)prop-2-enoicacid
    • 2-Propenoic acid, 3-(3,4-dihdroxyphenyl)-
    • trans-caffeic acid
    • NCGC00022654-06
    • (E)-3-(3,4-dihydroxyphenyl)acrylic acid
    • SR-01000000203
    • CS-0081280
    • SW197202-3
    • BBL012113
    • CAFFEIC ACID (IARC)
    • SR-01000000203-13
    • 3,4-dihydroxycinnamic acid (caffeic acid)
    • HMS3260J17
    • Caffeic acid, >=98.0% (HPLC)
    • BRD-K09900591-001-06-9
    • AB00490047
    • DTXSID901316055
    • 71693-97-5
    • Caffeic acid, matrix substance for MALDI-MS, >=99.0% (HPLC), powder, light beige
    • Caffeicacid
    • NCGC00017364-12
    • Tox21_500208
    • 3-(3,4-Dihydroxy phenyl)-2-propenoic acid
    • UNII-U2S3A33KVM', "4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene", '2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, (E)-
    • 4-(2-Carboxyethenyl)-1,2-dihydroxybenzene
    • (E)-3-(3,4-dihydroxyphenyl)acrylicacid
    • SMR000058214
    • SDCCGMLS-0002982.P003
    • Caffeic acid 1000 microg/mL in Acetone
    • C01481
    • DB-318886
    • NCGC00017364-05
    • CCG-38895
    • Caffeic Acid - CAS 331-39-5
    • BCP28271

Attributes

  • Canonical SMILES

    O=C(O)/C=C/C1=CC(O)=C(O)C=C1

  • InChI

    InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+

  • Molecule Class: Flavonoids
  • TPSA: 77.76
  • #RotBonds: 2
  • MW: 180.159
  • HBD: 3
  • HBA: 3
  • logP: 1.1956
  • Chemical Formula: C9H8O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862

External Databases


References

  • HPLC analysis and antimicrobial, antimycobacterial and antiviral activities of Tabernaemontana catharinensis A. DC Journal of Applied Biomedicine, 2015 (DOI).

Compound-Protein Relationships

Compound Activities

    • Antimycobacterial
    • Antiviral
    • Antiherpes
    • Antimicrobial
    • Antiherpetic
    • Cytotoxicity

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) -4.95
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.39
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.34

    Distribution Blood-Brain Barrier (Central Nervous System) -2.12
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.7
    Plasma Protein Binding 31.07
    Steady State Volume of Distribution 0.21

    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 Non-Inhibitor
    OATP1B3 Non-Inhibitor

    Excretion Clearance 9.38
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life >= 3hs

    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Safe
    Bioconcentration Factor -0.15
    Biodegradation Toxic
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Toxic
    Maximum Tolerated Dose 0.27
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 4.47
    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 3.11
    Rat (Acute) 1.78
    Rat (Chronic Oral) 2.91
    Fathead Minnow 4.01
    Respiratory Disease Safe
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe

    General Properties Boiling Point 356.62
    Hydration Free Energy -11.66
    Log(D) at pH=7.4 -1.56
    Log(P) 1.46
    Log S -1.63
    Log(Vapor Pressure) -6.19
    Melting Point 228.17
    pKa Acid 5.49
    pKa Basic 4.68