IMPPAT Phytochemical information: 
3,4-Dihydroxybenzoic acid
3,4-Dihydroxybenzoic acid
Summary

SMILES: OC(=O)c1ccc(c(c1)O)O
InChI: InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
InChIKey: YQUVCSBJEUQKSH-UHFFFAOYSA-N
DeepSMILES: OC=O)cccccc6)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: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Benzoic acids and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenolic acids (C6-C1)
NP Classifier Class: Simple phenolic acids
Synonymous chemical names:
3,4-dihydroxybenzoic-acid, protocatehuic acid, Protocatechuic acid, protacatechuic, protocatechuate, proto-catechuic acid, protocatechuic, protocatechuic acid, protocatechuic-acid, 3,4-dihydroxybenzoic acid
External chemical identifiers:
CID:CID_72; ChEMBL:CHEMBL37537; ChEBI:CHEBI:36062; ZINC:ZINC000000013246; FDASRS:36R5QJ8L4B; SureChEMBL:SCHEMBL39435; MolPort-000-881-444
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
3,4-Dihydroxybenzoic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 154.12
Log P RDKit 0.8
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 7
Number of heavy atoms RDKit 11
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 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 1
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
3,4-Dihydroxybenzoic acid
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.522491
3,4-Dihydroxybenzoic 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 -6.42
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 Yes
P-glycoprotein substrate SwissADME No
3,4-Dihydroxybenzoic acid
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000285ENSG00000137869CYP19A11588ChEMBL, NPASS
TAR_EXP_000253ENSG00000135047CTSL1514BindingDB, NPASS
TAR_EXP_000231ENSG00000101266CSNK2A11457ChEMBL, NPASS
TAR_EXP_000166ENSG00000163297ANTXR2118429NPASS
TAR_EXP_000500ENSG00000275565ALOX5240ChEMBL, NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000519ENSG00000171298GAA2548ChEMBL, NPASS
TAR_EXP_000492ENSG00000118298CA1423632BindingDB, ChEMBL, NPASS
TAR_EXP_000551ENSG00000236398TAS2R39259285ChEMBL, NPASS
TAR_EXP_000559ENSG00000185513L3MBTL126013NPASS
TAR_EXP_000608ENSG00000115419GLS2744NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000853ENSG00000276155MAPT4137NPASS
TAR_EXP_000883ENSG00000196611MMP14312ChEMBL, NPASS
TAR_EXP_000884ENSG00000087245MMP24313ChEMBL, NPASS
TAR_EXP_000885ENSG00000149968MMP34314ChEMBL, NPASS
TAR_EXP_000887ENSG00000118113MMP84317ChEMBL, NPASS
TAR_EXP_000888ENSG00000100985MMP94318ChEMBL, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_000053ENSG00000079337RAPGEF310411NPASS
TAR_EXP_001150ENSG00000070501POLB5423ChEMBL, NPASS
TAR_EXP_001299ENSG00000073756PTGS25743BindingDB, ChEMBL
TAR_EXP_001481ENSG00000007908SELE6401ChEMBL, NPASS
TAR_EXP_001482ENSG00000188404SELL6402ChEMBL, NPASS
TAR_EXP_001483ENSG00000174175SELP6403NPASS
TAR_EXP_001683ENSG00000133742CA1759BindingDB, ChEMBL, NPASS
TAR_EXP_001684ENSG00000104267CA2760BindingDB, ChEMBL, NPASS
TAR_EXP_001688ENSG00000131686CA6765ChEMBL, NPASS
TAR_EXP_001689ENSG00000168748CA7766BindingDB, ChEMBL, NPASS
TAR_EXP_000456ENSG00000085662AKR1B1231ChEMBL, NPASS
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL, NPASS
TAR_EXP_001690ENSG00000107159CA9768BindingDB, ChEMBL, NPASS
TAR_EXP_001691ENSG00000074410CA12771BindingDB, ChEMBL, NPASS
TAR_EXP_001810ENSG00000067955CBFB865NPASS
TAR_EXP_001273ENSG00000100804PSMB55693ChEMBL, NPASS
TAR_EXP_001686ENSG00000167434CA4762BindingDB, ChEMBL, NPASS