IMPPAT Phytochemical information: 
Dihydrocapsaicin

Dihydrocapsaicin
Summary

SMILES: COc1cc(CNC(=O)CCCCCCC(C)C)ccc1O
InChI: InChI=1S/C18H29NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21)
InChIKey: XJQPQKLURWNAAH-UHFFFAOYSA-N
DeepSMILES: COcccCNC=O)CCCCCCCC)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:
dihydrocapsaicin
External chemical identifiers:
CID:CID_107982; ChEMBL:CHEMBL311158; ChEBI:CHEBI:46932; ZINC:ZINC000002522581; FDASRS:W9BV32M08A; SureChEMBL:SCHEMBL119080; MolPort-001-742-258
Chemical structure download


Dihydrocapsaicin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 307.43
Log P RDKit 4.01
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 18
Number of heavy atoms RDKit 22
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 11
Shape complexity RDKit 0.61
Number of rotatable bonds RDKit 10
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


Dihydrocapsaicin
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.641999


Dihydrocapsaicin
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 -5.02
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 No
P-glycoprotein substrate SwissADME No


Dihydrocapsaicin
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL, NPASS
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL, NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559ChEMBL, NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000324ENSG00000184845DRD11812NPASS
TAR_EXP_000053ENSG00000079337RAPGEF310411NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001125ENSG00000127445PIN15300NPASS
TAR_EXP_001141ENSG00000109099PMP225376NPASS
TAR_EXP_001150ENSG00000070501POLB5423NPASS
TAR_EXP_001173ENSG00000196199MPHOSPH854737NPASS
TAR_EXP_000798ENSG00000055118KCNH23757NPASS
TAR_EXP_000818ENSG00000187258NPSR1387129NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001485ENSG00000197299BLM641NPASS
TAR_EXP_001631ENSG00000165409TSHR7253ChEMBL, NPASS
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001670ENSG00000196689TRPV17442ChEMBL, NPASS
TAR_EXP_000567ENSG00000177628GBA12629NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS