IMPPAT Phytochemical information: 
Vingramine
Vingramine
Summary

SMILES: C/C=C/1\CN2CC[C@]34[C@@H]([C@H]1CC[C@]23Nc1c4cc(c(c1C)c1cc2c3[C@H](C(=O)OC)[C@@H]4[C@@H]5CN([C@H](c3n(c2cc1OC)C)[C@H]4O[C@H]5C)C(=O)C(C)C)OC)C(=O)OC
InChI: InChI=1S/C46H56N4O8/c1-11-24-19-49-15-14-45-29-17-32(55-8)33(22(4)38(29)47-46(45,49)13-12-25(24)37(45)44(53)57-10)27-16-26-30(18-31(27)54-7)48(6)39-34(26)36(43(52)56-9)35-28-20-50(42(51)21(2)3)40(39)41(35)58-23(28)5/h11,16-18,21,23,25,28,35-37,40-41,47H,12-15,19-20H2,1-10H3/b24-11+/t23-,25-,28+,35-,36-,37-,40+,41-,45-,46-/m0/s1
InChIKey: OZBMAEUURAGYOB-NUPMTUBOSA-N
DeepSMILES: C/C=C\CNCC[C@][C@@H][C@H]\8CC[C@]96Ncc9cccc6C))cccc[C@H]C=O)OC)))[C@@H][C@@H]CN[C@H]c8nc%11cc%15OC)))))C)))[C@H]6O[C@H]7C)))))C=O)CC)C)))))))))))))OC)))))))))))C=O)OC
Scaffold Graph/Node/Bond level: C=C1CN2CCC34CC1CCC23Nc1cc(-c2ccc3[nH]c5c(c3c2)CC2C3CNC5C2OC3)ccc14
Scaffold Graph/Node level: CC1CN2CCC34CC1CCC23NC1CC(C2CCC3NC5C(CC6C7CNC5C6OC7)C3C2)CCC14
Scaffold Graph level: CC1CC2CCC34CC1CCC23CC1CC(C2CCC3CC5C(CC6C7CCC6C5CC7)C3C2)CCC14
Functional groups: CC(=O)N(C)C; C/C=C(\C)C; cN[C@](C)(C)N(C)C; cn(C)c; cOC; COC; COC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Carbazoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
vingramine
External chemical identifiers:
CID:CID_100933831
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Vingramine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 792.97
Log P RDKit 6.22
Topological polar surface area (Å2) RDKit 120.8
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 46
Number of heavy atoms RDKit 58
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 27
Shape complexity RDKit 0.59
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 6
Number of aliphatic rings RDKit 8
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 11
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 5
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 11
Vingramine
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 4
Ghose rule RDKit Failed
Veber rule RDKit Good
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 0.23
Vingramine
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 -7.59
Number of PAINS structural alerts SwissADME 2
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes