IMPPAT Phytochemical information: 
Benzenepropanoic acid, alpha,3,4-trihydroxy-, (aS)-

Benzenepropanoic acid, alpha,3,4-trihydroxy-, (aS)-
Summary

SMILES: OC(=O)[C@H](Cc1ccc(c(c1)O)O)O
InChI: InChI=1S/C9H10O5/c10-6-2-1-5(3-7(6)11)4-8(12)9(13)14/h1-3,8,10-12H,4H2,(H,13,14)/t8-/m0/s1
InChIKey: PAFLSMZLRSPALU-QMMMGPOBSA-N
DeepSMILES: OC=O)[C@H]Ccccccc6)O))O))))))O
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: CC(=O)O; cO; 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:
3-34-dihydroxyphenyllactic acid
External chemical identifiers:
CID:CID_179536; ZINC:ZINC000000895534; SureChEMBL:SCHEMBL5691448
Chemical structure download


Benzenepropanoic acid, alpha,3,4-trihydroxy-, (aS)-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 198.17
Log P RDKit 0.09
Topological polar surface area (Å2) RDKit 97.99
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 9
Number of heavy atoms RDKit 14
Number of heteroatoms RDKit 5
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 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


Benzenepropanoic acid, alpha,3,4-trihydroxy-, (aS)-
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 0.52


Benzenepropanoic acid, alpha,3,4-trihydroxy-, (aS)-
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 -7.65
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


Benzenepropanoic acid, alpha,3,4-trihydroxy-, (aS)-
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000216117HMOX1800
ENSP00000361850PLAU800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.