IMPPAT Phytochemical information: 
Harmine
Harmine
Summary

SMILES: COc1ccc2c(c1)[nH]c1c2ccnc1C
InChI: InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3
InChIKey: BXNJHAXVSOCGBA-UHFFFAOYSA-N
DeepSMILES: COcccccc6)[nH]cc5ccnc6C
Scaffold Graph/Node/Bond level: c1ccc2c(c1)[nH]c1cnccc12
Scaffold Graph/Node level: C1CCC2C(C1)NC1CNCCC12
Scaffold Graph level: C1CCC2C(C1)CC1CCCCC12
Functional groups: c[nH]c; cOC; cnc
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:
harmine, Harmine, Harminc
External chemical identifiers:
CID:CID_5280953; ChEMBL:CHEMBL269538; ChEBI:CHEBI:28121; ZINC:ZINC000018847046; FDASRS:4FHH5G48T7; SureChEMBL:SCHEMBL292955
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Harmine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 212.25
Log P RDKit 3.03
Topological polar surface area (Å2) RDKit 37.91
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 13
Number of heavy atoms RDKit 16
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 2
Shape complexity RDKit 0.15
Number of rotatable bonds RDKit 1
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
Harmine
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 0.672864
Harmine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -4.94
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 Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
Harmine
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_001796ENSG00000089022MAPKAPK58550ChEMBL, NPASS
TAR_EXP_001236ENSG00000185386MAPK115600ChEMBL, NPASS
TAR_EXP_001237ENSG00000050748MAPK95601ChEMBL, NPASS
TAR_EXP_001238ENSG00000109339MAPK105602ChEMBL, NPASS
TAR_EXP_001239ENSG00000156711MAPK135603ChEMBL, NPASS
TAR_EXP_001240ENSG00000169032MAP2K15604ChEMBL, NPASS
TAR_EXP_001253ENSG00000169035KLK75650BindingDB
TAR_EXP_000920ENSG00000065534MYLK4638ChEMBL, NPASS
TAR_EXP_000772ENSG00000184216IRAK13654ChEMBL, NPASS
TAR_EXP_000959ENSG00000117650NEK24751ChEMBL, NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL, NPASS
TAR_EXP_001235ENSG00000107643MAPK85599ChEMBL, NPASS
TAR_EXP_001075ENSG00000061273HDAC751564ChEMBL
TAR_EXP_001286ENSG00000101349PAK557144ChEMBL, NPASS
TAR_EXP_001295ENSG00000113240CLK457396BindingDB, ChEMBL, NPASS
TAR_EXP_001375ENSG00000067900ROCK16093BindingDB, ChEMBL
TAR_EXP_001429ENSG00000281877RPS6KA16195ChEMBL, NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000822ENSG00000182866LCK3932NPASS
TAR_EXP_001431ENSG00000177189RPS6KA36197ChEMBL, NPASS
TAR_EXP_001931ENSG00000165304MELK9833ChEMBL, NPASS
TAR_EXP_001930ENSG00000170312CDK1983BindingDB, ChEMBL
TAR_EXP_001432ENSG00000108443RPS6KB16198ChEMBL, NPASS
TAR_EXP_001272ENSG00000137843PAK656924NPASS
TAR_EXP_001467ENSG00000188130MAPK126300ChEMBL, NPASS
TAR_EXP_001231ENSG00000102882MAPK35595ChEMBL, NPASS
TAR_EXP_001227ENSG00000067606PRKCZ5590ChEMBL, NPASS
TAR_EXP_000842ENSG00000254087LYN4067BindingDB, NPASS
TAR_EXP_000845ENSG00000166949SMAD34088NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL, NPASS
TAR_EXP_000852ENSG00000069535MAOB4129NPASS
TAR_EXP_001222ENSG00000147099HDAC855869ChEMBL
TAR_EXP_001223ENSG00000184304PRKD15587ChEMBL, NPASS
TAR_EXP_001225ENSG00000268089GABRQ55879ChEMBL
TAR_EXP_000706ENSG00000291796APEX1328ChEMBL, NPASS
TAR_EXP_000855ENSG00000075413MARK34140ChEMBL, NPASS
TAR_EXP_000858ENSG00000198355PIM3415116BindingDB, ChEMBL, NPASS
TAR_EXP_001230ENSG00000100030MAPK15594BindingDB, ChEMBL, NPASS
TAR_EXP_000881ENSG00000087085ACHE43BindingDB, ChEMBL, NPASS
TAR_EXP_000728ENSG00000135312HTR1B3351BindingDB, ChEMBL, NPASS
TAR_EXP_000729ENSG00000179546HTR1D3352BindingDB, ChEMBL, NPASS
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL, NPASS
TAR_EXP_000734ENSG00000147246HTR2C3358BindingDB, ChEMBL, NPASS
TAR_EXP_000735ENSG00000166736HTR3A3359ChEMBL
TAR_EXP_000737ENSG00000157219HTR5A3361ChEMBL, NPASS
TAR_EXP_000738ENSG00000158748HTR63362BindingDB, ChEMBL, NPASS
TAR_EXP_000739ENSG00000148680HTR73363BindingDB, ChEMBL, NPASS
TAR_EXP_000755ENSG00000104365IKBKB3551ChEMBL, NPASS
TAR_EXP_001226ENSG00000065675PRKCQ5588NPASS
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL, NPASS
TAR_EXP_001795ENSG00000147082CCNB385417ChEMBL
TAR_EXP_001928ENSG00000068024HDAC49759ChEMBL
TAR_EXP_001911ENSG00000134318ROCK29475BindingDB, ChEMBL, NPASS
TAR_EXP_001843ENSG00000145386CCNA2890ChEMBL, NPASS
TAR_EXP_001834ENSG00000176749CDK5R18851BindingDB, ChEMBL, NPASS
TAR_EXP_001710ENSG00000114738MAPKAPK37867ChEMBL, NPASS
TAR_EXP_001087ENSG00000140992PDPK15170ChEMBL, NPASS
TAR_EXP_001831ENSG00000171720HDAC38841ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001723ENSG00000166908PIP4K2C79837ChEMBL, NPASS
TAR_EXP_001726ENSG00000163517HDAC1179885ChEMBL
TAR_EXP_001760ENSG00000177602HASPIN83903BindingDB, ChEMBL, NPASS
TAR_EXP_001761ENSG00000100429HDAC1083933ChEMBL, NPASS
TAR_EXP_001844ENSG00000133101CCNA18900ChEMBL, NPASS
TAR_EXP_001823ENSG00000010219DYRK48798BindingDB, ChEMBL, NPASS
TAR_EXP_001772ENSG00000143479DYRK38444BindingDB, ChEMBL, NPASS
TAR_EXP_001775ENSG00000127334DYRK28445BindingDB, ChEMBL, NPASS
TAR_EXP_001793ENSG00000134072CAMK18536ChEMBL, NPASS
TAR_EXP_001116ENSG00000078142PIK3C35289ChEMBL, NPASS
TAR_EXP_001119ENSG00000137193PIM15292ChEMBL, NPASS
TAR_EXP_001121ENSG00000105851PIK3CG5294ChEMBL, NPASS
TAR_EXP_001124ENSG00000143393PI4KB5298ChEMBL, NPASS
TAR_EXP_001139ENSG00000166851PLK15347ChEMBL, NPASS
TAR_EXP_001198ENSG00000288516PRKACA5566ChEMBL, NPASS
TAR_EXP_001801ENSG00000079277MKNK18569ChEMBL, NPASS
TAR_EXP_001768ENSG00000004660CAMKK184254ChEMBL, NPASS
TAR_EXP_001926ENSG00000048052HDAC99734ChEMBL
TAR_EXP_001845ENSG00000134057CCNB1891ChEMBL
TAR_EXP_001859ENSG00000134480CCNH902BindingDB, ChEMBL
TAR_EXP_001906ENSG00000118777ABCG29429BindingDB, ChEMBL, NPASS
TAR_EXP_001890ENSG00000081320STK17B9262ChEMBL, NPASS
TAR_EXP_001889ENSG00000162889MAPKAPK29261ChEMBL, NPASS
TAR_EXP_001887ENSG00000100784RPS6KA59252ChEMBL, NPASS
TAR_EXP_001885ENSG00000178999AURKB9212ChEMBL, NPASS
TAR_EXP_001468ENSG00000204842ATXN26311NPASS
TAR_EXP_001492ENSG00000118515SGK16446ChEMBL, NPASS
TAR_EXP_001518ENSG00000103546SLC6A26530BindingDB, ChEMBL, NPASS
TAR_EXP_001520ENSG00000108576SLC6A46532BindingDB, ChEMBL, NPASS
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001855ENSG00000162302RPS6KA48986ChEMBL, NPASS
TAR_EXP_001549ENSG00000166311SMPD16609ChEMBL, NPASS
TAR_EXP_001572ENSG00000104375STK36788ChEMBL, NPASS
TAR_EXP_001575ENSG00000008086CDKL56792ChEMBL, NPASS
TAR_EXP_001578ENSG00000105146AURKC6795ChEMBL, NPASS
TAR_EXP_001880ENSG00000149305HTR3B9177ChEMBL
TAR_EXP_001875ENSG00000105204DYRK1B9149ChEMBL, NPASS
TAR_EXP_001872ENSG00000157456CCNB29133ChEMBL, NPASS
TAR_EXP_001863ENSG00000129315CCNT1904BindingDB, ChEMBL
TAR_EXP_001861ENSG00000291428BRSK29024ChEMBL, NPASS
TAR_EXP_001207ENSG00000154229PRKCA5578BindingDB, ChEMBL, NPASS
TAR_EXP_001604ENSG00000163513TGFBR27048ChEMBL, NPASS
TAR_EXP_001559ENSG00000096063SRPK16732ChEMBL, NPASS
TAR_EXP_001220ENSG00000065243PKN25586ChEMBL, NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000532ENSG00000163285GABRG12565ChEMBL
TAR_EXP_000308ENSG00000178084HTR3C170572ChEMBL, NPASS
TAR_EXP_000291ENSG00000167657DAPK31613ChEMBL, NPASS
TAR_EXP_000290ENSG00000196730DAPK11612ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL, NPASS
TAR_EXP_000261ENSG00000169252ADRB2154BindingDB, ChEMBL, NPASS
TAR_EXP_000258ENSG00000043591ADRB1153BindingDB, ChEMBL, NPASS
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL, NPASS
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL, NPASS
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL, NPASS
TAR_EXP_000239ENSG00000120907ADRA1A148BindingDB, ChEMBL, NPASS
TAR_EXP_000236ENSG00000170214ADRA1B147ChEMBL, NPASS
TAR_EXP_000234ENSG00000230700CSNK2B1460ChEMBL
TAR_EXP_000232ENSG00000070770CSNK2A21459ChEMBL, NPASS
TAR_EXP_000231ENSG00000101266CSNK2A11457ChEMBL, NPASS
TAR_EXP_000671ENSG00000103319EEF2K29904ChEMBL, NPASS
TAR_EXP_000134ENSG00000180720CHRM41132ChEMBL
TAR_EXP_000137ENSG00000184984CHRM51133ChEMBL, NPASS
TAR_EXP_000167ENSG00000013441CLK11195BindingDB, ChEMBL, NPASS
TAR_EXP_000533ENSG00000113327GABRG22566ChEMBL
TAR_EXP_000169ENSG00000179335CLK31198ChEMBL
TAR_EXP_000215ENSG00000151414NEK7140609ChEMBL, NPASS
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL, NPASS
TAR_EXP_000222ENSG00000112062MAPK141432ChEMBL, NPASS
TAR_EXP_000226ENSG00000113712CSNK1A11452ChEMBL, NPASS
TAR_EXP_000227ENSG00000141551CSNK1D1453ChEMBL, NPASS
TAR_EXP_000228ENSG00000213923CSNK1E1454ChEMBL, NPASS
TAR_EXP_000229ENSG00000133275CSNK1G21455ChEMBL, NPASS
TAR_EXP_000685ENSG00000196591HDAC23066ChEMBL
TAR_EXP_000684ENSG00000116478HDAC13065BindingDB, ChEMBL, NPASS
TAR_EXP_000225ENSG00000103653CSK1445ChEMBL, NPASS
TAR_EXP_000325ENSG00000149295DRD21813ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000327ENSG00000069696DRD41815ChEMBL
TAR_EXP_000525ENSG00000186297GABRA52558ChEMBL
TAR_EXP_000526ENSG00000145863GABRA62559ChEMBL
TAR_EXP_000527ENSG00000163288GABRB12560ChEMBL
TAR_EXP_000528ENSG00000145864GABRB22561ChEMBL
TAR_EXP_000529ENSG00000166206GABRB32562ChEMBL
TAR_EXP_000530ENSG00000187730GABRD2563ChEMBL
TAR_EXP_000524ENSG00000109158GABRA42557ChEMBL
TAR_EXP_000659ENSG00000105723GSK3A2931BindingDB, ChEMBL, NPASS
TAR_EXP_000634ENSG00000099875MKNK22872ChEMBL, NPASS
TAR_EXP_000624ENSG00000186038HTR3E285242ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000572ENSG00000108773KAT2A2648NPASS
TAR_EXP_000535ENSG00000094755GABRP2568ChEMBL
TAR_EXP_000534ENSG00000182256GABRG32567ChEMBL
TAR_EXP_000636ENSG00000064393HIPK228996ChEMBL, NPASS
TAR_EXP_000133ENSG00000133019CHRM31131ChEMBL
TAR_EXP_000523ENSG00000011677GABRA32556ChEMBL
TAR_EXP_000660ENSG00000082701GSK3B2932BindingDB, ChEMBL, NPASS
TAR_EXP_000328ENSG00000169676DRD51816ChEMBL
TAR_EXP_000331ENSG00000157540DYRK1A1859BindingDB, ChEMBL, NPASS
TAR_EXP_000362ENSG00000186090HTR3D200909ChEMBL
TAR_EXP_000380ENSG00000163349HIPK1204851ChEMBL, NPASS
TAR_EXP_000390ENSG00000142208AKT1207ChEMBL, NPASS
TAR_EXP_000393ENSG00000105221AKT2208ChEMBL, NPASS
TAR_EXP_000522ENSG00000151834GABRA22555ChEMBL
TAR_EXP_000411ENSG00000165092ALDH1A1216ChEMBL, NPASS
TAR_EXP_000437ENSG00000274205MAPK15225689ChEMBL, NPASS
TAR_EXP_000454ENSG00000155111CDK1923097ChEMBL, NPASS
TAR_EXP_000489ENSG00000035664DAPK223604ChEMBL, NPASS
TAR_EXP_000504ENSG00000179593ALOX15B247NPASS
TAR_EXP_000515ENSG00000010810FYN2534NPASS
TAR_EXP_000521ENSG00000022355GABRA12554ChEMBL
TAR_EXP_000433ENSG00000168496FEN12237NPASS
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000168ENSG00000176444CLK21196BindingDB, ChEMBL, NPASS
TAR_EXP_000027ENSG00000123374CDK21017BindingDB, ChEMBL, NPASS
TAR_EXP_000101ENSG00000102096PIM211040ChEMBL, NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000078ENSG00000119408NEK610783ChEMBL, NPASS
TAR_EXP_000067BUB1B-PAK6106821730ChEMBL
TAR_EXP_000064ENSG00000110931CAMKK210645ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000107ENSG00000149554CHEK11111ChEMBL, NPASS
TAR_EXP_000042ENSG00000130669PAK410298ChEMBL, NPASS
TAR_EXP_000037ENSG00000132964CDK81024ChEMBL, NPASS
TAR_EXP_000036ENSG00000277273CDK71022BindingDB, ChEMBL, NPASS
TAR_EXP_000032ENSG00000164885CDK51020BindingDB, ChEMBL, NPASS
TAR_EXP_000023ENSG00000110422HIPK310114ChEMBL, NPASS
TAR_EXP_000005ENSG00000108840HDAC510014ChEMBL
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000038ENSG00000136807CDK91025BindingDB, ChEMBL, NPASS
TAR_EXP_000108ENSG00000122966CIT11113ChEMBL, NPASS
TAR_EXP_000531ENSG00000102287GABRE2564ChEMBL
TAR_EXP_000118ENSG00000183765CHEK211200ChEMBL, NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000116ENSG00000010322NISCH11188ChEMBL, NPASS
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000120ENSG00000090376IRAK311213ChEMBL, NPASS
TAR_EXP_000687ENSG00000100644HIF1A3091NPASS