Showing metabocard for Capsaicin (BMDB0002227)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:52:56 UTC
Update Date2020-04-22 15:10:17 UTC
BMDB IDBMDB0002227
Secondary Accession Numbers
  • BMDB02227
Metabolite Identification
Common NameCapsaicin
DescriptionCapsaicin, also known as zostrix or axsain, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Thus, capsaicin is considered to be a fatty amide. Based on a literature review very few articles have been published on Capsaicin.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(e)-8-Methyl-N-vanillyl-6-nonenamideChEBI
Isodecenoic acid vanillylamideChEBI
trans-8-Methyl-N-vanillyl-6-nonenamideChEBI
ZostrixChEBI
Isodecenoate vanillylamideGenerator
(e)-8-Methyl-N-vanillyl-6-nonenamide(8CL)HMDB
(e)8-Methyl-N-vanillyl-6-nonenamideHMDB
AxsainHMDB
e-CapsaicinHMDB
epsilon-CapsaicinHMDB
IsodecenoateHMDB
Isodecenoic acidHMDB
N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-trans-6-enamideHMDB
StyptysatHMDB
TransacinHMDB
GelcenHMDB
Link brand OF capsaicinHMDB
8 Methyl N vanillyl 6 nonenamideHMDB
Capsicum farmayaHMDB
CapzasinHMDB
Flemming brand OF capsaicinHMDB
8-Methyl-N-vanillyl-6-nonenamideHMDB
CapsinHMDB
KatrumHMDB
Medicis brand OF capsaicinHMDB
Smaller brand OF capsaicinHMDB
Thompson brand OF capsaicinHMDB
Vinas brand OF capsaicinHMDB
Alacan brand OF capsaicinHMDB
Antiphlogistine rub a-535 capsaicinHMDB
CapsaicineHMDB
CapsidolHMDB
Carter horner brand OF capsaicinHMDB
Centrum brand OF capsaicinHMDB
Elan brand OF capsaicinHMDB
ZacinHMDB
Chemical FormulaC18H27NO3
Average Molecular Weight305.4119
Monoisotopic Molecular Weight305.199093735
IUPAC Name(6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
Traditional Namecapsaicin
CAS Registry Number404-86-4
SMILES
COC1=C(O)C=CC(CNC(=O)CCCC\C=C\C(C)C)=C1
InChI Identifier
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+
InChI KeyYKPUWZUDDOIDPM-SOFGYWHQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Fatty acyl
  • Fatty amide
  • N-acyl-amine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Ether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point65 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.8ALOGPS
logP3.75ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.93ChemAxon
pKa (Strongest Basic)-0.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.56 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity90.32 m³·mol⁻¹ChemAxon
Polarizability36.32 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052o-9860000000-4151cd60d08276e5122aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03mi-9576000000-fb9f159d71790f546865View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0901000000-adba1bb6f254087febe8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , negativesplash10-014i-0900000000-5be0e66854b20d7a5a03View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-4337ff26dcbd2a77725eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-c94a246143850aa73e44View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014r-0950000000-3d145ef428e054b3e535View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014r-0950000000-c3ca097a6480ab798ff3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-4e8f98d1f848f30117d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-58fab2fdd15893ea71e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-296a0cb1555da4f1ccd7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0209000000-a91e6403d5a0c0b67c2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0209000000-dd0879d3f4f3a8b022c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0149000000-d6a9f6e70ae7cd7aec38View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0149000000-6fcf63c3bf44a4efc5bdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-06sl-0075690000-b562b766019cc7cbd98fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-01x3-0094560000-f354077f4cd51e45b945View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0002900000-ce1ea9819252343543cdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0002911000-6c37470f794c89a66410View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-00619747b8012ce6aa64View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-3ca73f5212a7643b45d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0912000000-95e090cebb8f95d7fe89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-6fb8b34936b848190c39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-4900000000-ade1e8ba842adf972c83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0419000000-80bfd538da9be3f08fe0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0922000000-00b0b7b3e9df2464d425View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-7900000000-8b112ae03b8d84d338f3View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002227
DrugBank IDDB06774
Phenol Explorer Compound ID712
FooDB IDFDB012411
KNApSAcK IDC00052221
Chemspider ID1265957
KEGG Compound IDC06866
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCapsaicin
METLIN IDNot Available
PubChem Compound1548943
PDB IDNot Available
ChEBI ID3374
References
Synthesis ReferenceGannett, Peter M.; Nagel, Donald L.; Reilly, Pam J.; Lawson, Terence; Sharpe, Jody; Toth, Bela. Capsaicinoids: their separation, synthesis, and mutagenicity. Journal of Organic Chemistry (1988), 53(5), 1064-71.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available