IMPPAT Phytochemical information: 
Desacetoxyvindorosine

Desacetoxyvindorosine
Summary

SMILES: COC(=O)[C@@]1(O)C[C@]2(CC)C=CC[NH+]3[C@@H]2[C@@]2(C1N(C)c1c2cccc1)CC3
InChI: InChI=1S/C22H28N2O3/c1-4-20-10-7-12-24-13-11-21(17(20)24)15-8-5-6-9-16(15)23(2)18(21)22(26,14-20)19(25)27-3/h5-10,17-18,26H,4,11-14H2,1-3H3/p+1/t17-,18?,20-,21+,22+/m0/s1
InChIKey: VCANAWRETHJMLW-CTILAWNOSA-O
DeepSMILES: COC=O)[C@@]O)C[C@]CC))C=CC[NH+][C@@H]6[C@@]C%10NC)cc5cccc6))))))))CC5
Scaffold Graph/Node/Bond level: C1=CC2CCC3Nc4ccccc4C34CC[NH+](C1)C24
Scaffold Graph/Node level: C1CCC2C(C1)NC1CCC3CCCN4CCC12C34
Scaffold Graph level: C1CCC2C(C1)CC1CCC3CCCC4CCC12C34
Functional groups: COC(C)=O; CO; CC=CC; C[NH+](C)C; cN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Plumeran-type alkaloids
Synonymous chemical names:
vindolidine
External chemical identifiers:
CID:CID_129320390
Chemical structure download


Desacetoxyvindorosine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 369.49
Log P RDKit 0.67
Topological polar surface area (Å2) RDKit 54.21
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 5
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 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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


Desacetoxyvindorosine
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 Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.59


Desacetoxyvindorosine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.57
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 No
P-glycoprotein substrate SwissADME Yes