IMPPAT Phytochemical information: 
(+/-)-Karachine
(+/-)-Karachine
Summary

SMILES: COc1ccc2c(c1OC)C1CC3(C2C2(N1CCc1c2cc2OCOc2c1)CC(=O)C3)C
InChI: InChI=1S/C26H27NO5/c1-25-10-15(28)11-26-17-9-21-20(31-13-32-21)8-14(17)6-7-27(26)18(12-25)22-16(24(25)26)4-5-19(29-2)23(22)30-3/h4-5,8-9,18,24H,6-7,10-13H2,1-3H3
InChIKey: CFSSZVBJSHOACV-UHFFFAOYSA-N
DeepSMILES: COcccccc6OC)))CCCC6CN6CCcc6ccOCOc5c9))))))))))))CC=O)C6)))))C
Scaffold Graph/Node/Bond level: O=C1CC2CC3c4ccccc4C2C2(C1)c1cc4c(cc1CCN32)OCO4
Scaffold Graph/Node level: OC1CC2CC3C4CCCCC4C2C2(C1)C1CC4OCOC4CC1CCN32
Scaffold Graph level: CC1CC2CC3C4CCCCC4C2C2(C1)C1CC4CCCC4CC1CCC32
Functional groups: cOC; CN(C)C; c1cOCO1; CC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Protoberberine alkaloids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Protoberberine alkaloids
Synonymous chemical names:
karachine
External chemical identifiers:
CID:CID_630739
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(+/-)-Karachine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 433.5
Log P RDKit 4.1
Topological polar surface area (Å2) RDKit 57.23
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 8
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
(+/-)-Karachine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.71
(+/-)-Karachine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.81
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No