IMPPAT Phytochemical information: 
3,4-Dihydroxyphenylacetic acid

3,4-Dihydroxyphenylacetic acid
Summary

SMILES: OC(=O)Cc1ccc(c(c1)O)O
InChI: InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
InChIKey: CFFZDZCDUFSOFZ-UHFFFAOYSA-N
DeepSMILES: OC=O)Ccccccc6)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: Phenols
ClassyFire Subclass: Benzenediols
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenolic acids (C6-C1)
NP Classifier Class: Simple phenolic acids
Synonymous chemical names:
homoprotocatechuic acid
External chemical identifiers:
CID:CID_547; ChEMBL:CHEMBL1284; ChEBI:CHEBI:41941; ZINC:ZINC000000388555; FDASRS:KEX5N0R4N5; SureChEMBL:SCHEMBL36348; MolPort-001-790-954
Chemical structure download


3,4-Dihydroxyphenylacetic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 168.15
Log P RDKit 0.72
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 8
Number of heavy atoms RDKit 12
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 1
Shape complexity RDKit 0.12
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


3,4-Dihydroxyphenylacetic 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 0
Ghose filter RDKit Passed
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 0.568512


3,4-Dihydroxyphenylacetic 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 -6.63
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


3,4-Dihydroxyphenylacetic 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_001726ENSG00000163517HDAC1179885ChEMBL
TAR_EXP_001631ENSG00000165409TSHR7253NPASS
TAR_EXP_001926ENSG00000048052HDAC99734ChEMBL
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000612ENSG00000127955GNAI12770NPASS
TAR_EXP_000608ENSG00000115419GLS2744NPASS
TAR_EXP_000551ENSG00000236398TAS2R39259285ChEMBL, NPASS
TAR_EXP_000519ENSG00000171298GAA2548NPASS
TAR_EXP_000510ENSG00000163286ALPG251BindingDB, NPASS
TAR_EXP_000507ENSG00000162551ALPL249BindingDB, NPASS
TAR_EXP_001761ENSG00000100429HDAC1083933ChEMBL, NPASS
TAR_EXP_000506ENSG00000163295ALPI248BindingDB, NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000005ENSG00000108840HDAC510014ChEMBL
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_001831ENSG00000171720HDAC38841ChEMBL
TAR_EXP_001923ENSG00000066135KDM4A9682ChEMBL, NPASS
TAR_EXP_000433ENSG00000168496FEN12237NPASS
TAR_EXP_000685ENSG00000196591HDAC23066ChEMBL
TAR_EXP_000684ENSG00000116478HDAC13065ChEMBL
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_001607ENSG00000090534THPO7066NPASS
TAR_EXP_001485ENSG00000197299BLM641NPASS
TAR_EXP_001368ENSG00000159788RGS126002NPASS
TAR_EXP_001366ENSG00000117152RGS45999NPASS
TAR_EXP_001222ENSG00000147099HDAC855869ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001173ENSG00000196199MPHOSPH854737NPASS
TAR_EXP_001150ENSG00000070501POLB5423NPASS
TAR_EXP_001141ENSG00000109099PMP225376NPASS
TAR_EXP_000687ENSG00000100644HIF1A3091NPASS
TAR_EXP_001928ENSG00000068024HDAC49759ChEMBL
TAR_EXP_001075ENSG00000061273HDAC751564ChEMBL
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_000853ENSG00000276155MAPT4137NPASS
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245ChEMBL, NPASS
TAR_EXP_000706ENSG00000291796APEX1328ChEMBL, NPASS