IMPPAT Phytochemical information: 
Veneserpine
Veneserpine
Summary

SMILES: COc1ccc2c(c1)[nH]c1c2CCN2[C@@H]1C[C@H]1[C@@H](C2)C[C@H]([C@@H]([C@H]1C(=O)OC)OC)OC(=O)c1cc(OC)c2c(c1)OCO2
InChI: InChI=1S/C32H36N2O9/c1-37-18-5-6-19-20-7-8-34-14-17-11-26(43-31(35)16-9-24(38-2)29-25(10-16)41-15-42-29)30(39-3)27(32(36)40-4)21(17)13-23(34)28(20)33-22(19)12-18/h5-6,9-10,12,17,21,23,26-27,30,33H,7-8,11,13-15H2,1-4H3/t17-,21+,23-,26-,27+,30+/m1/s1
InChIKey: NNFNBOIIPVQUQN-AROYDKDISA-N
DeepSMILES: COcccccc6)[nH]cc5CCN[C@@H]6C[C@H][C@@H]C6)C[C@H][C@@H][C@H]6C=O)OC))))OC)))OC=O)cccOC))ccc6)OCO5
Scaffold Graph/Node/Bond level: O=C(OC1CCC2CC3c4[nH]c5ccccc5c4CCN3CC2C1)c1ccc2c(c1)OCO2
Scaffold Graph/Node level: OC(OC1CCC2CC3C4NC5CCCCC5C4CCN3CC2C1)C1CCC2OCOC2C1
Scaffold Graph level: CC(CC1CCC2CC3C(CCC4C5CCCCC5CC34)CC2C1)C1CCC2CCCC2C1
Functional groups: cOC; c[nH]c; c1cOCO1; CN(C)C; COC(C)=O; COC; cC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Yohimbine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Yohimbine-like alkaloids
Synonymous chemical names:
veneserpine
External chemical identifiers:
CID:CID_101297737; ZINC:ZINC000238734448
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Veneserpine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 592.65
Log P RDKit 3.88
Topological polar surface area (Å2) RDKit 117.78
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 43
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Veneserpine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
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 0.42
Veneserpine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.14
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes