IMPPAT Phytochemical information: 
Harman
Harman
Summary

SMILES: Cc1nccc2c1[nH]c1c2cccc1
InChI: InChI=1S/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3
InChIKey: PSFDQSOCUJVVGF-UHFFFAOYSA-N
DeepSMILES: Ccncccc6[nH]cc5cccc6
Scaffold Graph/Node/Bond level: c1ccc2c(c1)[nH]c1cnccc12
Scaffold Graph/Node level: C1CCC2C(C1)NC1CNCCC12
Scaffold Graph level: C1CCC2C(C1)CC1CCCCC12
Functional groups: cnc; 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:
harman, Harman, passiflorine+, loturine, passiflorine, harmane
External chemical identifiers:
CID:CID_5281404; ChEMBL:CHEMBL12014; ChEBI:CHEBI:5623; ZINC:ZINC000006069162; FDASRS:82D6J0535P; SureChEMBL:SCHEMBL141723; MolPort-000-875-443
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Harman
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 182.23
Log P RDKit 3.02
Topological polar surface area (Å2) RDKit 28.68
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 14
Number of heteroatoms RDKit 2
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
Harman
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 0.568427
Harman
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 -5.08
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 Yes
Harman
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_001631ENSG00000165409TSHR7253NPASS
TAR_EXP_001710ENSG00000114738MAPKAPK37867ChEMBL, NPASS
TAR_EXP_001911ENSG00000134318ROCK29475ChEMBL, NPASS
TAR_EXP_001286ENSG00000101349PAK557144ChEMBL, NPASS
TAR_EXP_001796ENSG00000089022MAPKAPK58550ChEMBL, NPASS
TAR_EXP_001768ENSG00000004660CAMKK184254ChEMBL, NPASS
TAR_EXP_001772ENSG00000143479DYRK38444ChEMBL, NPASS
TAR_EXP_001775ENSG00000127334DYRK28445ChEMBL, NPASS
TAR_EXP_001793ENSG00000134072CAMK18536ChEMBL, NPASS
TAR_EXP_001801ENSG00000079277MKNK18569ChEMBL, NPASS
TAR_EXP_001728ENSG00000176208ATAD579915ChEMBL, NPASS
TAR_EXP_001771ENSG00000085999RAD54L8438ChEMBL, NPASS
TAR_EXP_001559ENSG00000096063SRPK16732ChEMBL, NPASS
TAR_EXP_001618ENSG00000198900TOP17150ChEMBL
TAR_EXP_001595ENSG00000262635TDO26999BindingDB, ChEMBL
TAR_EXP_001578ENSG00000105146AURKC6795ChEMBL, NPASS
TAR_EXP_001572ENSG00000104375STK36788ChEMBL, NPASS
TAR_EXP_001492ENSG00000118515SGK16446ChEMBL, NPASS
TAR_EXP_001485ENSG00000197299BLM641NPASS
TAR_EXP_001467ENSG00000188130MAPK126300ChEMBL, NPASS
TAR_EXP_001343ENSG00000114200BCHE590BindingDB, ChEMBL
TAR_EXP_001432ENSG00000108443RPS6KB16198ChEMBL, NPASS
TAR_EXP_001431ENSG00000177189RPS6KA36197ChEMBL, NPASS
TAR_EXP_001931ENSG00000165304MELK9833ChEMBL, NPASS
TAR_EXP_001429ENSG00000281877RPS6KA16195ChEMBL, NPASS
TAR_EXP_001366ENSG00000117152RGS45999NPASS
TAR_EXP_001306ENSG00000196396PTPN15770ChEMBL, NPASS
TAR_EXP_001272ENSG00000137843PAK656924NPASS
TAR_EXP_000437ENSG00000274205MAPK15225689ChEMBL, NPASS
TAR_EXP_001887ENSG00000100784RPS6KA59252ChEMBL, NPASS
TAR_EXP_000766ENSG00000131203IDO13620ChEMBL
TAR_EXP_001885ENSG00000178999AURKB9212ChEMBL, NPASS
TAR_EXP_000331ENSG00000157540DYRK1A1859BindingDB, ChEMBL, NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_001889ENSG00000162889MAPKAPK29261ChEMBL, NPASS
TAR_EXP_000390ENSG00000142208AKT1207ChEMBL, NPASS
TAR_EXP_000818ENSG00000187258NPSR1387129NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000853ENSG00000276155MAPT4137NPASS
TAR_EXP_000855ENSG00000075413MARK34140ChEMBL, NPASS
TAR_EXP_000858ENSG00000198355PIM3415116ChEMBL, NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000881ENSG00000087085ACHE43BindingDB, ChEMBL, NPASS
TAR_EXP_000393ENSG00000105221AKT2208ChEMBL, NPASS
TAR_EXP_000533ENSG00000113327GABRG22566ChEMBL
TAR_EXP_000532ENSG00000163285GABRG12565ChEMBL
TAR_EXP_000531ENSG00000102287GABRE2564ChEMBL
TAR_EXP_000530ENSG00000187730GABRD2563ChEMBL
TAR_EXP_000529ENSG00000166206GABRB32562ChEMBL
TAR_EXP_000527ENSG00000163288GABRB12560ChEMBL
TAR_EXP_000526ENSG00000145863GABRA62559ChEMBL, NPASS
TAR_EXP_000525ENSG00000186297GABRA52558ChEMBL
TAR_EXP_000755ENSG00000104365IKBKB3551ChEMBL, NPASS
TAR_EXP_000524ENSG00000109158GABRA42557ChEMBL
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_001861ENSG00000291428BRSK29024ChEMBL, NPASS
TAR_EXP_001844ENSG00000133101CCNA18900ChEMBL, NPASS
TAR_EXP_001843ENSG00000145386CCNA2890ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL, NPASS
TAR_EXP_000234ENSG00000230700CSNK2B1460ChEMBL
TAR_EXP_000232ENSG00000070770CSNK2A21459ChEMBL, NPASS
TAR_EXP_000231ENSG00000101266CSNK2A11457ChEMBL
TAR_EXP_000227ENSG00000141551CSNK1D1453ChEMBL, NPASS
TAR_EXP_000534ENSG00000182256GABRG32567ChEMBL
TAR_EXP_000225ENSG00000103653CSK1445ChEMBL, NPASS
TAR_EXP_000222ENSG00000112062MAPK141432ChEMBL, NPASS
TAR_EXP_000215ENSG00000151414NEK7140609ChEMBL, NPASS
TAR_EXP_000535ENSG00000094755GABRP2568ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000634ENSG00000099875MKNK22872ChEMBL, NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000118ENSG00000183765CHEK211200ChEMBL, NPASS
TAR_EXP_000107ENSG00000149554CHEK11111ChEMBL, NPASS
TAR_EXP_000636ENSG00000064393HIPK228996ChEMBL, NPASS
TAR_EXP_000660ENSG00000082701GSK3B2932ChEMBL, NPASS
TAR_EXP_000671ENSG00000103319EEF2K29904ChEMBL, NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000523ENSG00000011677GABRA32556ChEMBL
TAR_EXP_000528ENSG00000145864GABRB22561ChEMBL
TAR_EXP_000521ENSG00000022355GABRA12554ChEMBL
TAR_EXP_001223ENSG00000184304PRKD15587ChEMBL, NPASS
TAR_EXP_001225ENSG00000268089GABRQ55879ChEMBL
TAR_EXP_001227ENSG00000067606PRKCZ5590ChEMBL, NPASS
TAR_EXP_001230ENSG00000100030MAPK15594ChEMBL, NPASS
TAR_EXP_000027ENSG00000123374CDK21017ChEMBL, NPASS
TAR_EXP_000023ENSG00000110422HIPK310114ChEMBL, NPASS
TAR_EXP_000522ENSG00000151834GABRA22555ChEMBL
TAR_EXP_001220ENSG00000065243PKN25586ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_001235ENSG00000107643MAPK85599ChEMBL, NPASS
TAR_EXP_001236ENSG00000185386MAPK115600ChEMBL, NPASS
TAR_EXP_001237ENSG00000050748MAPK95601ChEMBL, NPASS
TAR_EXP_001238ENSG00000109339MAPK105602ChEMBL, NPASS
TAR_EXP_001239ENSG00000156711MAPK135603ChEMBL, NPASS
TAR_EXP_001240ENSG00000169032MAP2K15604ChEMBL, NPASS
TAR_EXP_000008ENSG00000153094BCL2L1110018BindingDB
TAR_EXP_001231ENSG00000102882MAPK35595ChEMBL, NPASS
TAR_EXP_000042ENSG00000130669PAK410298ChEMBL, NPASS
TAR_EXP_000032ENSG00000164885CDK51020ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_000101ENSG00000102096PIM211040ChEMBL, NPASS
TAR_EXP_000504ENSG00000179593ALOX15B247NPASS
TAR_EXP_000920ENSG00000065534MYLK4638ChEMBL, NPASS
TAR_EXP_000959ENSG00000117650NEK24751ChEMBL, NPASS
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_001207ENSG00000154229PRKCA5578ChEMBL, NPASS
TAR_EXP_001119ENSG00000137193PIM15292ChEMBL, NPASS
TAR_EXP_001139ENSG00000166851PLK15347ChEMBL, NPASS
TAR_EXP_001087ENSG00000140992PDPK15170ChEMBL, NPASS
TAR_EXP_000067BUB1B-PAK6106821730ChEMBL
TAR_EXP_000064ENSG00000110931CAMKK210645ChEMBL, NPASS
TAR_EXP_001198ENSG00000288516PRKACA5566ChEMBL, NPASS
TAR_EXP_000078ENSG00000119408NEK610783ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS