IMPPAT Phytochemical information: 
Harmol
Harmol
Summary

SMILES: O=c1ccc2c(c1)[nH]c1c2cc[nH]c1C
InChI: InChI=1S/C12H10N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-6,13-14H,1H3
InChIKey: LBBJNGFCXDOYMQ-UHFFFAOYSA-N
DeepSMILES: O=cccccc6)[nH]cc5cc[nH]c6C
Scaffold Graph/Node/Bond level: O=c1ccc2c(c1)[nH]c1c[nH]ccc12
Scaffold Graph/Node level: OC1CCC2C(C1)NC1CNCCC12
Scaffold Graph level: CC1CCC2C(C1)CC1CCCCC12
Functional groups: c=O; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Harmala alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carboline alkaloids
Synonymous chemical names:
harmol, 7-hydroxy-1-methyl-beta-carboline, Harmol
External chemical identifiers:
CID:CID_68094; ChEMBL:CHEMBL486817; ChEBI:CHEBI:95347; ZINC:ZINC000100076738; SureChEMBL:SCHEMBL10024119
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Harmol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 198.23
Log P RDKit 2.32
Topological polar surface area (Å2) RDKit 48.65
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 15
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 2
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 11
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.08
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 2
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
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 3
Harmol
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.571826
Harmol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.98
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
Harmol
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_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_001621ENSG00000141510TP537157NPASS
TAR_EXP_001549ENSG00000166311SMPD16609NPASS
TAR_EXP_001522ENSG00000158517NCF1653361BindingDB
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000271ENSG00000165841CYP2C191557NPASS
TAR_EXP_001775ENSG00000127334DYRK28445ChEMBL, NPASS
TAR_EXP_000650ENSG00000161800RACGAP129127ChEMBL, NPASS
TAR_EXP_000593ENSG00000102393GLA2717NPASS
TAR_EXP_000567ENSG00000177628GBA12629NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000392ENSG00000157554ERG2078NPASS
TAR_EXP_000331ENSG00000157540DYRK1A1859BindingDB, ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_001810ENSG00000067955CBFB865NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559NPASS
TAR_EXP_000083ENSG00000135346CGA1081NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000032ENSG00000164885CDK51020ChEMBL, NPASS
TAR_EXP_000027ENSG00000123374CDK21017ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_001728ENSG00000176208ATAD579915NPASS
TAR_EXP_001760ENSG00000177602HASPIN83903BindingDB, ChEMBL, NPASS
TAR_EXP_001771ENSG00000085999RAD54L8438ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_001150ENSG00000070501POLB5423NPASS
TAR_EXP_000766ENSG00000131203IDO13620BindingDB, NPASS
TAR_EXP_000747ENSG00000138413IDH13417NPASS