General Information of the Compound
Compound ID
CP0047227
Compound Name
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
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Synonyms
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
(E)-3-(3,4-dihydroxyphenyl)acrylic acid
2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-
3,4-Dihydroxy-trans-cinnamate
3,4-Dihydroxybenzeneacrylic acid
3,4-Dihydroxycinnamic Acid
3,4-Dihydroxycinnamic acid
3-(3,4-Dihydroxyphenyl)-2-propenoic acid
3-(3,4-Dihydroxyphenyl)propenoic acid
3-(3,4-dihydroxyphenyl)acrylic acid
331-39-5
4-(2-Carboxyethenyl)-1,2-dihydroxybenzene
501-16-6
Caffeic acid
Cinnamic acid, 3,4-dihydroxy-
UNII-U2S3A33KVM
caffeic acid
trans-Caffeate
trans-caffeic acid
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Structure
Formula
C9H8O4
Molecular Weight
180.159
Canonical SMILES
OC(=O)\C=C\c1ccc(O)c(O)c1
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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+
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InChIKey
QAIPRVGONGVQAS-DUXPYHPUSA-N
CAS
71693-97-5
501-16-6
Physicochemical Property
logP
1.1956
Rotatable Bonds
2
Heavy Atom Count
13
Polar Areas
77.76
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
3
Complexity
13

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 689043
SID: 22395875
ChEMBL ID
CHEMBL145
DrugBank ID
DB01880
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT01242, Polyunsaturated fatty acid 5-lipoxygenase
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293
 Cell Line Info 
Homo sapiens (Human)  1
1
IC50 = 25000 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 8500 nM
2 IC50 = 16700 nM
Protein ID: PT01743, Polyunsaturated fatty acid 5-lipoxygenase
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000194 RBL-1
 Cell Line Info 
Rattus norvegicus (Rat)  1
1
IC50 = 43000 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( 3,4-Dihydroxycinnamic Acid )
Drug Name 3,4-Dihydroxycinnamic Acid
Indication
Thrombocytopenia
Phase 4
Target(s)
Macrophage migration inhibitory factor (MIF)
 Target Info 
Inhibitor
Arachidonate 5-lipoxygenase (5-LOX)
 Target Info 
Inhibitor