IMPPAT Phytochemical information: 
2-(4-Hydroxyphenyl)propanoic acid

2-(4-Hydroxyphenyl)propanoic acid
Summary

SMILES: OC(=O)C(c1ccc(cc1)O)C
InChI: InChI=1S/C9H10O3/c1-6(9(11)12)7-2-4-8(10)5-3-7/h2-6,10H,1H3,(H,11,12)
InChIKey: ZHMMPVANGNPCBW-UHFFFAOYSA-N
DeepSMILES: OC=O)Ccccccc6))O)))))C
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:
2-(4-hydroxyphenyl)propionic acid
External chemical identifiers:
CID:CID_102526; ChEMBL:CHEMBL188281; ChEBI:CHEBI:1868; FDASRS:55FH3476SI; SureChEMBL:SCHEMBL288003; MolPort-004-946-886
Chemical structure download


2-(4-Hydroxyphenyl)propanoic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 166.18
Log P RDKit 1.58
Topological polar surface area (Å2) RDKit 57.53
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 9
Number of heavy atoms RDKit 12
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.11
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 2
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


2-(4-Hydroxyphenyl)propanoic 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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.7


2-(4-Hydroxyphenyl)propanoic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.20
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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