IMPPAT Phytochemical information: 
Bassianin
Bassianin
Summary

SMILES: CCC(/C=C(/C=C/C=C/C(=O)c1c(O)c(cn(c1=O)O)c1ccc(cc1)O)\C)C
InChI: InChI=1S/C23H25NO5/c1-4-15(2)13-16(3)7-5-6-8-20(26)21-22(27)19(14-24(29)23(21)28)17-9-11-18(25)12-10-17/h5-15,25,27,29H,4H2,1-3H3/b7-5+,8-6+,16-13+
InChIKey: LJUJZTYMRBJWDZ-ZDNNFFFZSA-N
DeepSMILES: CCC/C=C/C=C/C=C/C=O)ccO)ccnc6=O))O)))cccccc6))O)))))))))))))\C)))C
Scaffold Graph/Node/Bond level: O=c1ccc(-c2ccccc2)c[nH]1
Scaffold Graph/Node level: OC1CCC(C2CCCCC2)CN1
Scaffold Graph level: CC1CCC(C2CCCCC2)CC1
Functional groups: cC(=O)/C=C/C=C/C(C)=C/C; cO; cn(O)c; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Pyridines and derivatives
ClassyFire Subclass: Phenylpyridines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Nicotinic acid alkaloids
NP Classifier Class: Pyridine alkaloids
Synonymous chemical names:
bassianin, bassianin (yielding bassic acid arabinose,glucose, rhamnose, xylose, protobassic acid)
External chemical identifiers:
CID:CID_54714264
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Bassianin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 395.46
Log P RDKit 4.45
Topological polar surface area (Å2) RDKit 99.76
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 6
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 18
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.22
Number of rotatable bonds RDKit 7
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 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2
Bassianin
Drug-likeness properties
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.278305
Bassianin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.47
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No