IMPPAT Phytochemical information: 
Venoxidine
Venoxidine
Summary

SMILES: COC(=O)[C@@H]1[C@H](O)CC[C@H]2[C@@H]1C[C@@H]1c3[nH]c4c(c3CC[N+]1(C2)[O-])c(OC)ccc4
InChI: InChI=1S/C22H28N2O5/c1-28-18-5-3-4-15-19(18)13-8-9-24(27)11-12-6-7-17(25)20(22(26)29-2)14(12)10-16(24)21(13)23-15/h3-5,12,14,16-17,20,23,25H,6-11H2,1-2H3/t12-,14+,16-,17-,20+,24?/m1/s1
InChIKey: SANIGXXUGRLAGR-BXUFFXRESA-N
DeepSMILES: COC=O)[C@@H][C@H]O)CC[C@H][C@@H]6C[C@@H]c[nH]ccc5CC[N+]9C%13)[O-])))))cOC))ccc6
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)C1CC2CCCCC2C[NH+]1CC3
Scaffold Graph/Node level: C1CCC2CN3CCC4C5CCCCC5NC4C3CC2C1
Scaffold Graph level: C1CCC2CC3C(CCC4C5CCCCC5CC34)CC2C1
Functional groups: COC(C)=O; CO; c[nH]c; C[N+]([O-])(C)C; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Yohimbine alkaloids
Synonymous chemical names:
venoxidine, venoxidine(venenatine-nb-oxide), Venoxidine
External chemical identifiers:
CID:CID_12444713; ZINC:ZINC000238785134
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Venoxidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 400.48
Log P RDKit 2.67
Topological polar surface area (Å2) RDKit 94.61
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.59
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
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 5
Venoxidine
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 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.46
Venoxidine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.03
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes