IMPPAT Phytochemical information: 
9H-Pyrido[3,4-B]indole
9H-Pyrido[3,4-B]indole
Summary

SMILES: c1ccc2c(c1)[nH]c1c2ccnc1
InChI: InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H
InChIKey: AIFRHYZBTHREPW-UHFFFAOYSA-N
DeepSMILES: cccccc6)[nH]cc5ccnc6
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: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Pyridoindoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carboline alkaloids
Synonymous chemical names:
β-carboline, harman, nor, norharmane, Norharmane, Norharman, beta-carboline, 9h-pyrido[3,4-b]indole, norharman
External chemical identifiers:
CID:CID_64961; ChEMBL:CHEMBL275224; ChEBI:CHEBI:109895; ZINC:ZINC000000066039; FDASRS:94HMA1I78O; SureChEMBL:SCHEMBL25834; MolPort-000-141-389
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
9H-Pyrido[3,4-B]indole
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 168.2
Log P RDKit 2.72
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 11
Number of heavy atoms RDKit 13
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 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 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
9H-Pyrido[3,4-B]indole
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 0.548949
9H-Pyrido[3,4-B]indole
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
9H-Pyrido[3,4-B]indole
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_001200ENSG00000142875PRKACB5567ChEMBL
TAR_EXP_001198ENSG00000288516PRKACA5566BindingDB, ChEMBL
TAR_EXP_001119ENSG00000137193PIM15292ChEMBL, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_000852ENSG00000069535MAOB4129ChEMBL, NPASS
TAR_EXP_000881ENSG00000087085ACHE43BindingDB, ChEMBL
TAR_EXP_001201ENSG00000165059PRKACG5568ChEMBL, NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL, NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000786ENSG00000177606JUN3725NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_001207ENSG00000154229PRKCA5578BindingDB, ChEMBL
TAR_EXP_001216ENSG00000163558PRKCI5584ChEMBL
TAR_EXP_001212ENSG00000163932PRKCD5580ChEMBL
TAR_EXP_001213ENSG00000171132PRKCE5581ChEMBL
TAR_EXP_001214ENSG00000126583PRKCG5582ChEMBL
TAR_EXP_001215ENSG00000027075PRKCH5583ChEMBL
TAR_EXP_000766ENSG00000131203IDO13620BindingDB, ChEMBL, NPASS
TAR_EXP_001223ENSG00000184304PRKD15587ChEMBL
TAR_EXP_001225ENSG00000268089GABRQ55879ChEMBL
TAR_EXP_001226ENSG00000065675PRKCQ5588ChEMBL, NPASS
TAR_EXP_001227ENSG00000067606PRKCZ5590ChEMBL
TAR_EXP_001343ENSG00000114200BCHE590BindingDB, ChEMBL
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001574ENSG00000087586AURKA6790ChEMBL, NPASS
TAR_EXP_001595ENSG00000262635TDO26999BindingDB, ChEMBL
TAR_EXP_001618ENSG00000198900TOP17150ChEMBL
TAR_EXP_001209ENSG00000166501PRKCB5579ChEMBL
TAR_EXP_000755ENSG00000104365IKBKB3551ChEMBL, NPASS
TAR_EXP_000534ENSG00000182256GABRG32567ChEMBL
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_000027ENSG00000123374CDK21017ChEMBL, NPASS
TAR_EXP_000032ENSG00000164885CDK51020ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000157ENSG00000213341CHUK1147BindingDB, ChEMBL, NPASS
TAR_EXP_000231ENSG00000101266CSNK2A11457ChEMBL
TAR_EXP_000232ENSG00000070770CSNK2A21459ChEMBL, NPASS
TAR_EXP_000234ENSG00000230700CSNK2B1460ChEMBL
TAR_EXP_000331ENSG00000157540DYRK1A1859BindingDB, ChEMBL
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000496ENSG00000115825PRKD323683ChEMBL
TAR_EXP_000521ENSG00000022355GABRA12554ChEMBL
TAR_EXP_000522ENSG00000151834GABRA22555ChEMBL
TAR_EXP_000523ENSG00000011677GABRA32556ChEMBL
TAR_EXP_000524ENSG00000109158GABRA42557ChEMBL
TAR_EXP_000525ENSG00000186297GABRA52558ChEMBL
TAR_EXP_000526ENSG00000145863GABRA62559ChEMBL, NPASS
TAR_EXP_000527ENSG00000163288GABRB12560ChEMBL
TAR_EXP_000528ENSG00000145864GABRB22561ChEMBL
TAR_EXP_000529ENSG00000166206GABRB32562ChEMBL
TAR_EXP_000530ENSG00000187730GABRD2563ChEMBL
TAR_EXP_000531ENSG00000102287GABRE2564ChEMBL
TAR_EXP_000532ENSG00000163285GABRG12565ChEMBL
TAR_EXP_000533ENSG00000113327GABRG22566ChEMBL
TAR_EXP_001728ENSG00000176208ATAD579915NPASS
TAR_EXP_000535ENSG00000094755GABRP2568ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000720ENSG00000106211HSPB13315NPASS
TAR_EXP_001911ENSG00000134318ROCK29475BindingDB
TAR_EXP_001170ENSG00000112033PPARD5467NPASS