IMPPAT Phytochemical information: 
Catechol

Catechol
Summary

SMILES: Oc1ccccc1O
InChI: InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
InChIKey: YCIMNLLNPGFGHC-UHFFFAOYSA-N
DeepSMILES: Occcccc6O
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenols
ClassyFire Subclass: Benzenediols
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
Synonymous chemical names:
catechol, Catechol, (+)-catechol, (+)-pyrocatechol, catechol(pyrocatechin), (+)catechol, pyrocatechol
External chemical identifiers:
CID:CID_289; ChEMBL:CHEMBL280998; ChEBI:CHEBI:18135; ZINC:ZINC000013512214; FDASRS:LF3AJ089DQ; SureChEMBL:SCHEMBL18351; MolPort-000-871-939
Chemical structure download


Catechol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 110.11
Log P RDKit 1.1
Topological polar surface area (Å2) RDKit 40.46
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 6
Number of heavy atoms RDKit 8
Number of heteroatoms RDKit 2
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 6
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 0
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


Catechol
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.490728


Catechol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.35
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


Catechol
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_000433ENSG00000168496FEN12237ChEMBL, NPASS
TAR_EXP_000461ENSG00000102755FLT12321ChEMBL
TAR_EXP_000492ENSG00000118298CA1423632BindingDB, ChEMBL, NPASS
TAR_EXP_000500ENSG00000275565ALOX5240ChEMBL, NPASS
TAR_EXP_000503ENSG00000161905ALOX15246ChEMBL, NPASS
TAR_EXP_000504ENSG00000179593ALOX15B247NPASS
TAR_EXP_000505ENSG00000198793MTOR2475ChEMBL, NPASS
TAR_EXP_000515ENSG00000010810FYN2534ChEMBL, NPASS
TAR_EXP_000539ENSG00000115828QPCT25797BindingDB, ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL, NPASS
TAR_EXP_000608ENSG00000115419GLS2744NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216ChEMBL, NPASS
TAR_EXP_001753ENSG00000137752CASP1834ChEMBL
TAR_EXP_001181ENSG00000166148AVPR1A552ChEMBL
TAR_EXP_001186ENSG00000138814PPP3CA5530ChEMBL
TAR_EXP_001811ENSG00000138735PDE5A8654ChEMBL
TAR_EXP_001837ENSG00000163394CCKAR886ChEMBL
TAR_EXP_001900ENSG00000123595RAB9A9367NPASS
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL
TAR_EXP_000701ENSG00000164120HPGD3248ChEMBL, NPASS
TAR_EXP_000559ENSG00000185513L3MBTL126013ChEMBL, NPASS
TAR_EXP_000397ENSG00000140009ESR22100ChEMBL
TAR_EXP_000357ENSG00000277571ELANE1991ChEMBL
TAR_EXP_000387ENSG00000141736ERBB22064ChEMBL
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL
TAR_EXP_000267ENSG00000188778ADRB3155ChEMBL
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL
TAR_EXP_000273ENSG00000138109CYP2C91559ChEMBL
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL
TAR_EXP_000277ENSG00000130649CYP2E11571ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000325ENSG00000149295DRD21813ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL, NPASS
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL
TAR_EXP_000261ENSG00000169252ADRB2154ChEMBL
TAR_EXP_000327ENSG00000069696DRD41815ChEMBL
TAR_EXP_000258ENSG00000043591ADRB1153ChEMBL
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL
TAR_EXP_000250ENSG00000100448CTSG1511ChEMBL
TAR_EXP_000332ENSG00000180772AGTR2186ChEMBL
TAR_EXP_000339ENSG00000151617EDNRA1909ChEMBL
TAR_EXP_000348ENSG00000146648EGFR1956ChEMBL, NPASS
TAR_EXP_000265ENSG00000255974CYP2A61548ChEMBL
TAR_EXP_001173ENSG00000196199MPHOSPH854737ChEMBL, NPASS
TAR_EXP_001117ENSG00000121879PIK3CA5290BindingDB, ChEMBL, NPASS
TAR_EXP_000233ENSG00000171873ADRA1D146ChEMBL
TAR_EXP_000862ENSG00000166603MC4R4160ChEMBL
TAR_EXP_000178ENSG00000160791CCR51234ChEMBL
TAR_EXP_000177ENSG00000183813CCR41233ChEMBL
TAR_EXP_000137ENSG00000184984CHRM51133ChEMBL
TAR_EXP_000134ENSG00000180720CHRM41132ChEMBL
TAR_EXP_000133ENSG00000133019CHRM31131ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000122ENSG00000169239CA5B11238BindingDB, ChEMBL, NPASS
TAR_EXP_000119ENSG00000101751POLI11201ChEMBL, NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_001727ENSG00000004948CALCR799ChEMBL
TAR_EXP_001691ENSG00000074410CA12771BindingDB, ChEMBL, NPASS
TAR_EXP_001690ENSG00000107159CA9768BindingDB, NPASS
TAR_EXP_001689ENSG00000168748CA7766BindingDB, NPASS
TAR_EXP_001688ENSG00000131686CA6765NPASS
TAR_EXP_001687ENSG00000174990CA5A763BindingDB, ChEMBL, NPASS
TAR_EXP_001686ENSG00000167434CA4762BindingDB, ChEMBL, NPASS
TAR_EXP_001685ENSG00000164879CA3761BindingDB, ChEMBL, NPASS
TAR_EXP_001684ENSG00000104267CA2760BindingDB, ChEMBL, NPASS
TAR_EXP_001683ENSG00000133742CA1759BindingDB, ChEMBL, NPASS
TAR_EXP_001678ENSG00000158125XDH7498ChEMBL, NPASS
TAR_EXP_000861ENSG00000124089MC3R4159ChEMBL
TAR_EXP_000081ENSG00000173198CYSLTR110800ChEMBL
TAR_EXP_000863ENSG00000176136MC5R4161ChEMBL
TAR_EXP_000867ENSG00000135679MDM24193BindingDB, ChEMBL, NPASS
TAR_EXP_000881ENSG00000087085ACHE43ChEMBL
TAR_EXP_000883ENSG00000196611MMP14312ChEMBL, NPASS
TAR_EXP_000222ENSG00000112062MAPK141432ChEMBL
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_000203ENSG00000128271ADORA2A135ChEMBL
TAR_EXP_000200ENSG00000163485ADORA1134ChEMBL
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL
TAR_EXP_001171ENSG00000132170PPARG5468NPASS
TAR_EXP_001170ENSG00000112033PPARD5467NPASS
TAR_EXP_001151ENSG00000170734POLH5429NPASS
TAR_EXP_001150ENSG00000070501POLB5423ChEMBL, NPASS
TAR_EXP_001141ENSG00000109099PMP225376NPASS
TAR_EXP_001125ENSG00000127445PIN15300NPASS
TAR_EXP_001923ENSG00000066135KDM4A9682ChEMBL, NPASS
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_001059ENSG00000122008POLK51426ChEMBL, NPASS
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001002ENSG00000082556OPRK14986ChEMBL
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL
TAR_EXP_000988ENSG00000185149NPY2R4887ChEMBL
TAR_EXP_000987ENSG00000164128NPY1R4886ChEMBL
TAR_EXP_000983ENSG00000141458NPC14864NPASS
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL, NPASS
TAR_EXP_000888ENSG00000100985MMP94318ChEMBL, NPASS
TAR_EXP_000887ENSG00000118113MMP84317ChEMBL, NPASS
TAR_EXP_000885ENSG00000149968MMP34314ChEMBL, NPASS
TAR_EXP_000884ENSG00000087245MMP24313ChEMBL, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001942ENSG00000012504NR1H49971NPASS
TAR_EXP_000041ENSG00000147955SIGMAR110280ChEMBL
TAR_EXP_000687ENSG00000100644HIF1A3091ChEMBL, NPASS
TAR_EXP_000738ENSG00000158748HTR63362ChEMBL
TAR_EXP_000734ENSG00000147246HTR2C3358ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL
TAR_EXP_000720ENSG00000106211HSPB13315NPASS
TAR_EXP_000715ENSG00000044574HSPA53309NPASS
TAR_EXP_000706ENSG00000291796APEX1328ChEMBL, NPASS
TAR_EXP_001458ENSG00000168398BDKRB2624ChEMBL
TAR_EXP_001378ENSG00000143365RORC6097ChEMBL, NPASS
TAR_EXP_001373ENSG00000239713APOBEC3G60489NPASS
TAR_EXP_001366ENSG00000117152RGS45999NPASS
TAR_EXP_001360ENSG00000004700RECQL5965ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001207ENSG00000154229PRKCA5578ChEMBL
TAR_EXP_001230ENSG00000100030MAPK15594ChEMBL
TAR_EXP_001231ENSG00000102882MAPK35595ChEMBL
TAR_EXP_001289ENSG00000169403PTAFR5724ChEMBL
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL
TAR_EXP_001300ENSG00000160801PTH1R5745NPASS
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000692ENSG00000113161HMGCR3156ChEMBL
TAR_EXP_001320ENSG00000262418PTPRC5788ChEMBL
TAR_EXP_000747ENSG00000138413IDH13417NPASS
TAR_EXP_000759ENSG00000169429CXCL83576NPASS
TAR_EXP_000704ENSG00000113749HRH23274ChEMBL
TAR_EXP_000761ENSG00000180871CXCR23579ChEMBL
TAR_EXP_001642ENSG00000121807CCR2729230ChEMBL
TAR_EXP_001607ENSG00000090534THPO7066NPASS
TAR_EXP_001592ENSG00000059377TBXAS16916ChEMBL
TAR_EXP_000760ENSG00000163464CXCR13577ChEMBL
TAR_EXP_001587ENSG00000115353TACR16869ChEMBL
TAR_EXP_001585ENSG00000075073TACR26865ChEMBL
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001485ENSG00000197299BLM641NPASS
TAR_EXP_001669ENSG00000114812VIPR17433ChEMBL
TAR_EXP_000786ENSG00000177606JUN3725NPASS
TAR_EXP_001468ENSG00000204842ATXN26311NPASS
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_000798ENSG00000055118KCNH23757ChEMBL
TAR_EXP_000819ENSG00000235268KDM4E390245ChEMBL, NPASS
TAR_EXP_000822ENSG00000182866LCK3932ChEMBL
TAR_EXP_000766ENSG00000131203IDO13620ChEMBL, NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000853ENSG00000276155MAPT4137NPASS
TAR_EXP_000833ENSG00000160789LMNA4000NPASS