NPs Basic Information

Name
Caffeic Acid
Molecular Formula C9H8O4
IUPAC Name*
(E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
SMILES
C1=CC(=C(C=C1/C=C/C(=O)O)O)O
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+
InChIKey
QAIPRVGONGVQAS-DUXPYHPUSA-N
Synonyms
caffeic acid; 3,4-Dihydroxycinnamic acid; 331-39-5; trans-caffeic acid; 501-16-6; 3,4-Dihydroxybenzeneacrylic acid; 3-(3,4-dihydroxyphenyl)acrylic acid; (E)-3-(3,4-dihydroxyphenyl)acrylic acid; (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid; Caffeicacid; Cinnamic acid, 3,4-dihydroxy-; 3-(3,4-Dihydroxyphenyl)-2-propenoic acid; (E)-3,4-dihydroxycinnamic acid; 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-; trans-Caffeate; 4-(2-Carboxyethenyl)-1,2-dihydroxybenzene; 3,4-Dihydroxy-trans-cinnamate; 3-(3,4-Dihydroxyphenyl)propenoic acid; 4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene; NSC 57197; Caffeate; 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, (E)-; 3-(3,4-Dihydroxy phenyl)-2-propenoic acid; NSC-57197; 71693-97-5; CHEMBL145; NSC-623438; U2S3A33KVM; (E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid; AI3-63211; MLS000069738; CHEBI:16433; trans-3,4-Dihydroxycinnamic Acid; NSC57197; 331-89-5; SMR000058214; (2E)-3-(3,4-dihydroxyphenyl)acrylic acid; 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, (2E)-; MFCD00004392; Caffeic acid - Natural; CCRIS 847; 3-(3,4-dihydroxyphenyl)prop-2-enoic acid; HSDB 7088; SR-01000000203; EINECS 206-361-2; UNII-U2S3A33KVM; CHEBI:36281; caffeic-acid; Caffeic acid pure; Caffeic acid, 1; Caffeic acid 1000 microg/mL in Acetone; 3,4-dihydroxycinnamic acid (caffeic acid); Caffeic Acid,(S); Caffeic acid, trans-; 3,4-dihydroxycinnamate; CAFFEIC ACID natural; Opera_ID_1700; CAFFEIC ACID [MI]; CAFFEIC ACID [DSC]; Cinnamic acid,4-dihydroxy-; 3,4-Dihydroxycinnamic acid, predominantly trans; CAFFEIC ACID [HSDB]; CAFFEIC ACID [IARC]; CAFFEIC ACID [INCI]; 3,4-Dihydroxybenzeneacrylate; SCHEMBL23358; MLS001076493; MLS002207132; MLS002222302; MLS006011849; BIDD:ER0456; SPECTRUM1503987; CAFFEIC ACID [WHO-DD]; 2-Propenoic acid,3-(3,4-dihydroxyphenyl)-, (2E)-; 3,4-Dihydroxycinnamate, XVII; BDBM4375; cid_689043; GTPL5155; ZINC58172; AMY3943; DTXSID901316055; HMS2235G09; HMS3260J17; HMS3649O17; BCP28271; HY-N0172; Tox21_500208; BBL012113; Caffeic Acid - CAS 331-39-5; CCG-38895; NSC623438; s2277; STK397812; Caffeic acid, >=98.0% (HPLC); 2-Propenoic acid,4-dihydroxyphenyl)-; AKOS000144463; AC-8006; CS-8205; DB01880; LP00208; SDCCGMLS-0002982.P003; SDCCGSBI-0050196.P004; NCGC00017364-04; NCGC00017364-05; NCGC00017364-06; NCGC00017364-07; NCGC00017364-08; NCGC00017364-09; NCGC00017364-10; NCGC00017364-11; NCGC00017364-12; NCGC00017364-13; NCGC00017364-22; NCGC00022654-03; NCGC00022654-04; NCGC00022654-05; NCGC00022654-06; NCGC00022654-07; NCGC00022654-08; NCGC00022654-09; NCGC00260893-01; (E)-3-(3,4-dihydroxyphenyl)acrylicacid; AS-10895; BP-30112; SMR004703501; XC164210; Caffeic acid, purum, >=95.0% (HPLC); AB00490047; EU-0100208; SW197202-3; 2-Morpholin-4-yl-isonicotinicacidhydrochloride; (E)-3-(3,4-dihydroxyphenyl)prop-2-enoicacid; C 0625; C-1500; C01197; C01481; EN300-1067793; (2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid; 331C395; A851723; Q414116; SR-01000000203-2; SR-01000000203-6; SR-01000000203-7; SR-01000000203-8; BRD-K09900591-001-06-9; SR-01000000203-13; CAFFEIC ACID (CONSTITUENT OF BLACK COHOSH) [DSC]; F3096-1708; Z240113804; 8B3E4DA7-F3B0-4972-A315-2E387071737F; trans-Caffeic acid, certified reference material, TraceCERT(R); Caffeic acid, matrix substance for MALDI-MS, >=99.0% (HPLC); Caffeic acid, United States Pharmacopeia (USP) Reference Standard; Caffeic acid, matrix substance for MALDI-MS, >=99.0% (HPLC), powder, light beige
CAS 331-39-5
PubChem CID 689043
ChEMBL ID CHEMBL145
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Phenylpropanoids and poly
      • Class: Cinnamic acids and deriva
        • Subclass: Hydroxycinnamic acids and
          • Direct Parent: Hydroxycinnamic acids

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference
Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference

NPs Content

*Note: The vaules in Content Percentage are calculated by dividing the content value by the maximum content value in NP Content.
**Note: The units with different NP content, due to their incomparable values, are separated into different tables.

NPs Biological Activity

Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name
Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name

NPs Physi-Chem Properties

Molecular Weight: 180.16 ALogp: 1.2
HBD: 3 HBA: 4
Rotatable Bonds: 2 Lipinski's rule of five: Accepted
Polar Surface Area: 77.8 Aromatic Rings: 1
Heavy Atoms: 13 QED Weighted: 0.477

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -5.22 MDCK Permeability: 0.00001100
Pgp-inhibitor: 0 Pgp-substrate: 0.024
Human Intestinal Absorption (HIA): 0.009 20% Bioavailability (F20%): 0.009
30% Bioavailability (F30%): 0.454

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.119 Plasma Protein Binding (PPB): 87.70%
Volume Distribution (VD): 0.37 Fu: 11.07%

ADMET: Metabolism

CYP1A2-inhibitor: 0.048 CYP1A2-substrate: 0.069
CYP2C19-inhibitor: 0.036 CYP2C19-substrate: 0.046
CYP2C9-inhibitor: 0.27 CYP2C9-substrate: 0.231
CYP2D6-inhibitor: 0.014 CYP2D6-substrate: 0.164
CYP3A4-inhibitor: 0.043 CYP3A4-substrate: 0.038

ADMET: Excretion

Clearance (CL): 10.973 Half-life (T1/2): 0.93

ADMET: Toxicity

hERG Blockers: 0.018 Human Hepatotoxicity (H-HT): 0.73
Drug-inuced Liver Injury (DILI): 0.365 AMES Toxicity: 0.183
Rat Oral Acute Toxicity: 0.833 Maximum Recommended Daily Dose: 0.049
Skin Sensitization: 0.942 Carcinogencity: 0.233
Eye Corrosion: 0.602 Eye Irritation: 0.972
Respiratory Toxicity: 0.422
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

Similar NPs Similar Drugs
NPs ID NPs 2D Structure Similarity Score TTD ID Drug 2D Structure Similarity Score
ENC001101 0.659 D0V9EN 1.000
ENC000002 0.561 D08HVR 0.469
ENC001420 0.545 D0I3RO 0.451
ENC000035 0.523 D0BA6T 0.451
ENC001547 0.478 D01ZJK 0.435
ENC004024 0.473 D0P7JZ 0.426
ENC000127 0.469 D07MOX 0.396
ENC001543 0.457 D0C4YC 0.391
ENC001917 0.457 D0U0OT 0.389
ENC001471 0.457 D0T7OW 0.383
*Note: the compound similarity was calculated by RDKIT.