IMPPAT Phytochemical information: 
Bruceolline B
Bruceolline B
Summary

SMILES: OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3cc4nccc5c4n(c3=O)c3ccccc53)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C26H28N2O12/c29-8-15-18(30)20(32)22(34)25(39-15)37-9-16-19(31)21(33)23(35)26(40-16)38-14-7-12-17-11(5-6-27-12)10-3-1-2-4-13(10)28(17)24(14)36/h1-7,15-16,18-23,25-26,29-35H,8-9H2/t15-,16-,18-,19-,20+,21+,22-,23-,25-,26-/m1/s1
InChIKey: VNELTEBGMWTQED-NXEOTYAVSA-N
DeepSMILES: OC[C@H]O[C@@H]OC[C@H]O[C@@H]Occcncccc6nc%10=O))cccccc96))))))))))))))))[C@@H][C@H][C@@H]6O))O))O)))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1c(OC2CCCC(COC3CCCCO3)O2)cc2nccc3c4ccccc4n1c23
Scaffold Graph/Node level: OC1C(OC2CCCC(COC3CCCCO3)O2)CC2NCCC3C4CCCCC4N1C23
Scaffold Graph level: CC1C(CC2CCCC(CCC3CCCCC3)C2)CC2CCCC3C4CCCCC4C1C23
Functional groups: CO; CO[C@@H](C)OC; cO[C@@H](C)OC; cnc; cn(c)c; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Indolonaphthyridine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carboline alkaloids
Synonymous chemical names:
bruceacanthinoside
External chemical identifiers:
CID:CID_190940; ZINC:ZINC000141224676
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Bruceolline B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 560.51
Log P RDKit -2.56
Topological polar surface area (Å2) RDKit 212.9
Number of hydrogen bond acceptors RDKit 14
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 40
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.38
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.46
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 3
Number of aromatic rings RDKit 4
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Bruceolline B
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.13
Bruceolline B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.90
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 Yes