IMPPAT Phytochemical information: 
Capsaicin
Capsaicin
Summary

SMILES: COc1cc(CNC(=O)CCCC/C=C/C(C)C)ccc1O
InChI: InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+
InChIKey: YKPUWZUDDOIDPM-SOFGYWHQSA-N
DeepSMILES: COcccCNC=O)CCCC/C=C/CC)C)))))))))))ccc6O
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: C/C=C/C; CNC(C)=O; cO; cOC
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:
capsaicin, capsidol
External chemical identifiers:
CID:1548943; ChEMBL:CHEMBL294199; ChEBI:3374; ZINC:ZINC000001530575; FDASRS:S07O44R1ZM; SureChEMBL:SCHEMBL8085; MolPort-001-742-263
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Capsaicin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit
Capsaicin
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 0.54
Capsaicin
ADMET 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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.62
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
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
Capsaicin
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000159060NOX3829
ENSP00000162749TNFRSF1A824
ENSP00000212015SIRT1800
ENSP00000215832MAPK1700
ENSP00000216117HMOX1824
ENSP00000216629BDKRB1865
ENSP00000216797NFKBIA700
ENSP00000217244CSNK2A1700
ENSP00000225577RPS6KB1700
ENSP00000226730IL2800
ENSP00000241261TNFSF10700
ENSP00000252809GDF15938
ENSP00000256383EIF2S1700
ENSP00000258743IL6952
ENSP00000260682CYP2C9700
ENSP00000261740TRPV4893
ENSP00000262209TRPA1794
ENSP00000262461SLC12A2814
ENSP00000262999UCP1800
ENSP00000263025MAPK3780
ENSP00000263341IL1B736
ENSP00000264634WNT5A800
ENSP00000264657STAT3745
ENSP00000264708POMC840
ENSP00000265310TRPV5702
ENSP00000265643GAL830
ENSP00000269305TP53943
ENSP00000270202AKT1742
ENSP00000275493EGFR722
ENSP00000275525IGFBP1800
ENSP00000278616ATM938
ENSP00000283916TMPRSS11D786
ENSP00000286122BANP800
ENSP00000287820PPARG733
ENSP00000297494NOS3736
ENSP00000303522TACR1926
ENSP00000304592FASN800
ENSP00000304845UGT1A1700
ENSP00000306245FOS987
ENSP00000306512IL8955
ENSP00000309629CFL1700
ENSP00000311032CASP3953
ENSP00000313420PRKDC700
ENSP00000318822BID700
ENSP00000320171PKM819
ENSP00000321106TAC1988
ENSP00000323926TRPM8845
ENSP00000324173HSPA5700
ENSP00000327251NOS2709
ENSP00000329357SP1700
ENSP00000329623BCL2743
ENSP00000330237CASP9700
ENSP00000331358GAST819
ENSP00000331746CALCA756
ENSP00000335657CCK873
ENSP00000337146ENOX2973
ENSP00000337459NOS1853
ENSP00000337915CYP3A4700
ENSP00000342007CYP1A2728
ENSP00000342222TRPV2905
ENSP00000343204JAK1700
ENSP00000343838UGT1A10700
ENSP00000344352ATF3833
ENSP00000344460CBS821
ENSP00000346017CALCB700
ENSP00000346768UGT1A9700
ENSP00000347379OCLN800
ENSP00000350941SRC728
ENSP00000351273CASP8700
ENSP00000352358TRPV6880
ENSP00000353483MAPK8945
ENSP00000353820CYP2D6700
ENSP00000354394STAT1800
ENSP00000354558MTOR700
ENSP00000355759PARP1700
ENSP00000356436PLA2G4A700
ENSP00000356438PTGS2830
ENSP00000358327CASP7700
ENSP00000358335MAP3K7700
ENSP00000358511CNR1751
ENSP00000360372CYP2C19700
ENSP00000361125VEGFA943
ENSP00000361405MMP9838
ENSP00000362403TACR2827
ENSP00000362525UGT1A7700
ENSP00000362549UGT1A8700
ENSP00000364310H2AFX700
ENSP00000365025CSNK2B700
ENSP00000368683EDN1753
ENSP00000368686E2F4800
ENSP00000380252NFE2L2700
ENSP00000382659TRPV1999
ENSP00000384273RELA700
ENSP00000387230UPP2850
ENSP00000387662GCG818
ENSP00000388566CASP4700
ENSP00000389338MAPK9722
ENSP00000398698TNF742
ENSP00000417229EIF2A700
ENSP00000431418NTRK1935
ENSP00000435591MUC5AC700
ENSP00000436812MUC5B700
ENSP00000447803DDIT3824
ENSP00000459962999
ENSP00000461518TRPV3859
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.