IMPPAT Phytochemical information: 
Citbismine A
Citbismine A
Summary

SMILES: COc1cc2[nH]c3c(OC)c(OC)ccc3c(=O)c2c(c1C1c2c(OC1C(O)(C)C)cc(c1c2n(C)c2c(c1=O)cccc2O)O)O
InChI: InChI=1S/C35H32N2O10/c1-35(2,43)34-26(24-21(47-34)13-18(39)23-29(24)37(3)28-15(31(23)41)8-7-9-17(28)38)25-20(45-5)12-16-22(32(25)42)30(40)14-10-11-19(44-4)33(46-6)27(14)36-16/h7-13,26,34,38-39,42-43H,1-6H3,(H,36,40)
InChIKey: FTTSBKFANOKIKQ-UHFFFAOYSA-N
DeepSMILES: COccc[nH]ccOC))cOC))ccc6c=O)c%10cc%14CccOC5CO)C)C))))cccc6nC)ccc6=O))cccc6O))))))))))O)))))))O
Scaffold Graph/Node/Bond level: O=c1c2ccccc2[nH]c2ccc(C3COc4ccc5c(=O)c6ccccc6[nH]c5c43)cc12
Scaffold Graph/Node level: OC1C2CCCCC2NC2CCC(C3COC4CCC5C(O)C6CCCCC6NC5C43)CC21
Scaffold Graph level: CC1C2CCCCC2CC2CCC(C3CCC4CCC5C(C)C6CCCCC6CC5C43)CC21
Functional groups: cOC; cn(C)c; c[nH]c; c=O; cO; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Benzoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Anthranilic acid alkaloids
NP Classifier Class: Acridone alkaloids
Synonymous chemical names:
citbismine a
External chemical identifiers:
CID:CID_131753020
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Citbismine A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 640.65
Log P RDKit 4.49
Topological polar surface area (Å2) RDKit 172.7
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 35
Number of heavy atoms RDKit 47
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 26
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.26
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 6
Total number of rings RDKit 7
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 7
Citbismine A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.17
Citbismine A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -6.25
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No