IMPPAT Phytochemical information: 
Buchananine

Buchananine
Summary

SMILES: O[C@H]1O[C@H](COC(=O)c2cccnc2)[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C12H15NO7/c14-8-7(20-12(18)10(16)9(8)15)5-19-11(17)6-2-1-3-13-4-6/h1-4,7-10,12,14-16,18H,5H2/t7-,8-,9+,10-,12+/m1/s1
InChIKey: ASJDJBXXEHTEBW-GPTQDWHKSA-N
DeepSMILES: O[C@H]O[C@H]COC=O)ccccnc6)))))))))[C@H][C@@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(OCC1CCCCO1)c1cccnc1
Scaffold Graph/Node level: OC(OCC1CCCCO1)C1CCCNC1
Scaffold Graph level: CC(CCC1CCCCC1)C1CCCCC1
Functional groups: CO[C@H](O)C; cC(=O)OC; cnc; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Pyridines and derivatives
ClassyFire Subclass: Pyridinecarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Nicotinic acid alkaloids
NP Classifier Class: Pyridine alkaloids
Synonymous chemical names:
pyridine alkaloid buchananine, buchananine
External chemical identifiers:
CID:CID_442629; ChEBI:CHEBI:3202; ZINC:ZINC000004098573
Chemical structure download


Buchananine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 285.25
Log P RDKit -1.96
Topological polar surface area (Å2) RDKit 129.34
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.42
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Buchananine
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 1
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.47


Buchananine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.45
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No