IMPPAT Phytochemical information: 
3-(3,4-Dihydroxyphenyl)propionic acid

3-(3,4-Dihydroxyphenyl)propionic acid
Summary

SMILES: OC(=O)CCc1ccc(c(c1)O)O
InChI: InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)
InChIKey: DZAUWHJDUNRCTF-UHFFFAOYSA-N
DeepSMILES: OC=O)CCcccccc6)O))O
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: CC(=O)O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Phenylpropanoic acids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
Synonymous chemical names:
3-(3,4-dihydroxyphenyl)propanoic acid, hydrocaffeic acid, dihydrocaffeic acid
External chemical identifiers:
CID:CID_348154; ChEMBL:CHEMBL136927; ChEBI:CHEBI:48400; ZINC:ZINC000000388044; FDASRS:MSW0228VUB; SureChEMBL:SCHEMBL245530; MolPort-001-790-947
Chemical structure download


3-(3,4-Dihydroxyphenyl)propionic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 182.18
Log P RDKit 1.12
Topological polar surface area (Å2) RDKit 77.76
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 9
Number of heavy atoms RDKit 13
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.22
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1


3-(3,4-Dihydroxyphenyl)propionic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.61


3-(3,4-Dihydroxyphenyl)propionic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.79
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


3-(3,4-Dihydroxyphenyl)propionic acid
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000263321TYR739
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.