IMPPAT Phytochemical information: 
Caffeic acid
Caffeic acid
Summary

SMILES: OC(=O)/C=C/c1ccc(c(c1)O)O
InChI: InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
InChIKey: QAIPRVGONGVQAS-DUXPYHPUSA-N
DeepSMILES: OC=O)/C=C/cccccc6)O))O
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: c/C=C/C(=O)O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Cinnamic acids and derivatives
ClassyFire Subclass: Hydroxycinnamic acids and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acids and derivatives
Synonymous chemical names:
34-dihydroxycinnamic acid, caffeic acids, 3,4-dihydroxycinnamic-acid, 3,4-dihydroxycinnamic acid, caffeic, caffeic acid, caffeic-acid, 3-34-dihydroxyphenyl-2-propenoic acid
External chemical identifiers:
CID:CID_689043; ChEMBL:CHEMBL145; ChEBI:CHEBI:16433; ZINC:ZINC000000058172; FDASRS:U2S3A33KVM; SureChEMBL:SCHEMBL23358; MolPort-000-742-954
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Caffeic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 180.16
Log P RDKit 1.2
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 9
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
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
Caffeic 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 0.471621
Caffeic 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 -6.58
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
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
Caffeic 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_000500ENSG00000275565ALOX5240BindingDB, ChEMBL, NPASS
TAR_EXP_000519ENSG00000171298GAA2548ChEMBL, NPASS
TAR_EXP_000456ENSG00000085662AKR1B1231ChEMBL, NPASS
TAR_EXP_000491ENSG00000186318BACE123621BindingDB, ChEMBL
TAR_EXP_000492ENSG00000118298CA1423632BindingDB, ChEMBL, NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL, NPASS
TAR_EXP_000322ENSG00000197635DPP41803BindingDB, ChEMBL, NPASS
TAR_EXP_000330ENSG00000144891AGTR1185BindingDB, ChEMBL
TAR_EXP_000329ENSG00000108861DUSP31845BindingDB, ChEMBL, NPASS
TAR_EXP_000298ENSG00000151632AKR1C21646ChEMBL, NPASS
TAR_EXP_000297ENSG00000187134AKR1C11645ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576NPASS
TAR_EXP_000166ENSG00000163297ANTXR2118429NPASS
TAR_EXP_000122ENSG00000169239CA5B11238BindingDB, ChEMBL, NPASS
TAR_EXP_000104ENSG00000198610AKR1C41109ChEMBL, NPASS
TAR_EXP_000551ENSG00000236398TAS2R39259285ChEMBL, NPASS
TAR_EXP_000348ENSG00000146648EGFR1956BindingDB, NPASS
TAR_EXP_000593ENSG00000102393GLA2717NPASS
TAR_EXP_000881ENSG00000087085ACHE43BindingDB, ChEMBL, NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000888ENSG00000100985MMP94318BindingDB, ChEMBL, NPASS
TAR_EXP_000894ENSG00000103152MPG4350ChEMBL, NPASS
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_001059ENSG00000122008POLK51426NPASS
TAR_EXP_001075ENSG00000061273HDAC751564ChEMBL
TAR_EXP_001141ENSG00000109099PMP225376NPASS
TAR_EXP_001150ENSG00000070501POLB5423NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_000884ENSG00000087245MMP24313ChEMBL, NPASS
TAR_EXP_001222ENSG00000147099HDAC855869ChEMBL
TAR_EXP_001280ENSG00000198074AKR1B1057016ChEMBL, NPASS
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL, NPASS
TAR_EXP_001299ENSG00000073756PTGS25743BindingDB, ChEMBL, NPASS
TAR_EXP_001306ENSG00000196396PTPN15770BindingDB, ChEMBL, NPASS
TAR_EXP_001312ENSG00000143851PTPN75778BindingDB, ChEMBL, NPASS
TAR_EXP_001609ENSG00000151090THRB7068NPASS
TAR_EXP_001636ENSG00000118271TTR7276ChEMBL, NPASS
TAR_EXP_001647ENSG00000077498TYR7299ChEMBL, NPASS
TAR_EXP_001230ENSG00000100030MAPK15594NPASS
TAR_EXP_000883ENSG00000196611MMP14312ChEMBL, NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000853ENSG00000276155MAPT4137NPASS
TAR_EXP_000635ENSG00000167701GPT2875ChEMBL, NPASS
TAR_EXP_000674ENSG00000123636BAZ2B29994NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000684ENSG00000116478HDAC13065BindingDB, ChEMBL
TAR_EXP_000685ENSG00000196591HDAC23066ChEMBL
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_000722ENSG00000080824HSP90AA13320BindingDB
TAR_EXP_000723ENSG00000096384HSP90AB13326NPASS
TAR_EXP_000740ENSG00000114378HYAL13373BindingDB, NPASS
TAR_EXP_000743ENSG00000182782HCAR2338442ChEMBL, NPASS
TAR_EXP_000752ENSG00000142192APP351BindingDB, ChEMBL, NPASS
TAR_EXP_000798ENSG00000055118KCNH23757NPASS
TAR_EXP_000814ENSG00000108424KPNB13837NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245ChEMBL, NPASS
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000846ENSG00000100299ARSA410NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000852ENSG00000069535MAOB4129ChEMBL
TAR_EXP_000608ENSG00000115419GLS2744NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_001683ENSG00000133742CA1759BindingDB, ChEMBL, NPASS
TAR_EXP_000017ENSG00000169371SNUPN10073NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000005ENSG00000108840HDAC510014ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000076ENSG00000117139KDM5B10765ChEMBL
TAR_EXP_001678ENSG00000158125XDH7498ChEMBL, NPASS
TAR_EXP_001684ENSG00000104267CA2760BindingDB, ChEMBL, NPASS
TAR_EXP_001685ENSG00000164879CA3761BindingDB, ChEMBL, NPASS
TAR_EXP_001686ENSG00000167434CA4762BindingDB, ChEMBL, NPASS
TAR_EXP_001928ENSG00000068024HDAC49759ChEMBL
TAR_EXP_001688ENSG00000131686CA6765ChEMBL, NPASS
TAR_EXP_001689ENSG00000168748CA7766BindingDB, ChEMBL, NPASS
TAR_EXP_001687ENSG00000174990CA5A763BindingDB, ChEMBL, NPASS
TAR_EXP_001831ENSG00000171720HDAC38841ChEMBL
TAR_EXP_001690ENSG00000107159CA9768BindingDB, ChEMBL, NPASS
TAR_EXP_001691ENSG00000074410CA12771BindingDB, ChEMBL, NPASS
TAR_EXP_001726ENSG00000163517HDAC1179885ChEMBL
TAR_EXP_001761ENSG00000100429HDAC1083933ChEMBL, NPASS
TAR_EXP_001807ENSG00000196139AKR1C38644ChEMBL, NPASS
TAR_EXP_001926ENSG00000048052HDAC99734ChEMBL
TAR_EXP_001923ENSG00000066135KDM4A9682NPASS