IMPPAT Phytochemical information: 
beta-Belladonnine

beta-Belladonnine
Summary

SMILES: CN1C2CCC1CC(C2)OC(=O)[C@@H]1CCC(c2c1cccc2)(C(=O)OC1CC2CCC(C1)N2C)c1ccccc1
InChI: InChI=1S/C34H42N2O4/c1-35-23-12-13-24(35)19-27(18-23)39-32(37)30-16-17-34(22-8-4-3-5-9-22,31-11-7-6-10-29(30)31)33(38)40-28-20-25-14-15-26(21-28)36(25)2/h3-11,23-28,30H,12-21H2,1-2H3/t23?,24?,25?,26?,27?,28?,30-,34?/m1/s1
InChIKey: GERIGMSHTUAXSI-KUONIBBMSA-N
DeepSMILES: CNCCCC5CCC7)OC=O)[C@@H]CCCcc6cccc6))))))C=O)OCCCCCCC7)N5C))))))))))cccccc6
Scaffold Graph/Node/Bond level: O=C(OC1CC2CCC(C1)N2)C1CCC(C(=O)OC2CC3CCC(C2)N3)(c2ccccc2)c2ccccc21
Scaffold Graph/Node level: OC(OC1CC2CCC(C1)N2)C1CCC(C2CCCCC2)(C(O)OC2CC3CCC(C2)N3)C2CCCCC12
Scaffold Graph level: CC(CC1CC2CCC(C2)C1)C1CCC(C(C)CC2CC3CCC(C3)C2)(C2CCCCC2)C2CCCCC12
Functional groups: CN(C)C; COC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Naphthalenes
ClassyFire Subclass: Naphthalenecarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Tropane alkaloids
Synonymous chemical names:
beta belladonine
External chemical identifiers:
CID:CID_101614998
Chemical structure download


beta-Belladonnine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 542.72
Log P RDKit 5.19
Topological polar surface area (Å2) RDKit 59.08
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 34
Number of heavy atoms RDKit 40
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 20
Shape complexity RDKit 0.59
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7


beta-Belladonnine
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 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 0.49


beta-Belladonnine
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.37
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No