IMPPAT Phytochemical information: 
Homodihydrocapsaicin

Homodihydrocapsaicin
Summary

SMILES: COc1cc(CNC(=O)CCCCCCCC(C)C)ccc1O
InChI: InChI=1S/C19H31NO3/c1-15(2)9-7-5-4-6-8-10-19(22)20-14-16-11-12-17(21)18(13-16)23-3/h11-13,15,21H,4-10,14H2,1-3H3,(H,20,22)
InChIKey: AKDLSISGGARWFP-UHFFFAOYSA-N
DeepSMILES: COcccCNC=O)CCCCCCCCC)C))))))))))))ccc6O
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: cOC; CNC(C)=O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenols
ClassyFire Subclass: Methoxyphenols
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Capsaicins and Capsaicinoids|Phenylalanine-derived alkaloids
Synonymous chemical names:
homodihydrocapsaicin
External chemical identifiers:
CID:CID_3084336; ChEBI:CHEBI:174344; ZINC:ZINC000013383221; FDASRS:QE35S0T20Z; SureChEMBL:SCHEMBL1870592; MolPort-044-726-990
Chemical structure download


Homodihydrocapsaicin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 321.46
Log P RDKit 4.4
Topological polar surface area (Å2) RDKit 58.56
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.63
Number of rotatable bonds RDKit 11
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1


Homodihydrocapsaicin
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 Bad
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 0.59


Homodihydrocapsaicin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.73
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No