IMPPAT Phytochemical information: 
3,8-Dimethyl-3-(4-methylpent-3-en-1-yl)-3,11-dihydropyrano[3,2-a]carbazol-9-ol
3,8-Dimethyl-3-(4-methylpent-3-en-1-yl)-3,11-dihydropyrano[3,2-a]carbazol-9-ol
Summary

SMILES: CC(=CCCC1(C)C=Cc2c(O1)ccc1c2[nH]c2c1cc(c(c2)O)C)C
InChI: InChI=1S/C23H25NO2/c1-14(2)6-5-10-23(4)11-9-17-21(26-23)8-7-16-18-12-15(3)20(25)13-19(18)24-22(16)17/h6-9,11-13,24-25H,5,10H2,1-4H3
InChIKey: WWXYBSVWYPHUPZ-UHFFFAOYSA-N
DeepSMILES: CC=CCCCC)C=CccO6)cccc6[nH]cc5cccc6)O))C))))))))))))))))))C
Scaffold Graph/Node/Bond level: C1=Cc2c(ccc3c2[nH]c2ccccc23)OC1
Scaffold Graph/Node level: C1CCC2C(C1)NC1C3CCCOC3CCC21
Scaffold Graph level: C1CCC2C(C1)CC1C3CCCCC3CCC21
Functional groups: CC=C(C)C; cC=CC; cOC; c[nH]c; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Carbazoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carbazole alkaloids
Synonymous chemical names:
Isomahanine, isomahanine
External chemical identifiers:
CID:CID_375148; ChEMBL:CHEMBL498436; SureChEMBL:SCHEMBL13142235; MolPort-001-740-435
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
3,8-Dimethyl-3-(4-methylpent-3-en-1-yl)-3,11-dihydropyrano[3,2-a]carbazol-9-ol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 347.46
Log P RDKit 6.25
Topological polar surface area (Å2) RDKit 45.25
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.04
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.3
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4
3,8-Dimethyl-3-(4-methylpent-3-en-1-yl)-3,11-dihydropyrano[3,2-a]carbazol-9-ol
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.55035
3,8-Dimethyl-3-(4-methylpent-3-en-1-yl)-3,11-dihydropyrano[3,2-a]carbazol-9-ol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -3.97
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
3,8-Dimethyl-3-(4-methylpent-3-en-1-yl)-3,11-dihydropyrano[3,2-a]carbazol-9-ol
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_001468ENSG00000204842ATXN26311NPASS
TAR_EXP_000853ENSG00000276155MAPT4137NPASS
TAR_EXP_000845ENSG00000166949SMAD34088NPASS
TAR_EXP_000818ENSG00000187258NPSR1387129NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001551ENSG00000145335SNCA6622NPASS
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001230ENSG00000100030MAPK15594NPASS
TAR_EXP_000747ENSG00000138413IDH13417NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_000604ENSG00000112164GLP1R2740NPASS
TAR_EXP_000519ENSG00000171298GAA2548NPASS
TAR_EXP_000475ENSG00000120948TARDBP23435NPASS
TAR_EXP_000433ENSG00000168496FEN12237NPASS
TAR_EXP_000083ENSG00000135346CGA1081NPASS
TAR_EXP_000053ENSG00000079337RAPGEF310411NPASS
TAR_EXP_001923ENSG00000066135KDM4A9682ChEMBL, NPASS
TAR_EXP_001728ENSG00000176208ATAD579915NPASS
TAR_EXP_001630ENSG00000074319TSG1017251NPASS
TAR_EXP_000674ENSG00000123636BAZ2B29994NPASS
TAR_EXP_000947ENSG00000149311ATM472NPASS