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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:42:14 UTC
Update Date2022-03-07 02:54:14 UTC
HMDB IDHMDB0034780
Secondary Accession Numbers
  • HMDB34780
Metabolite Identification
Common NameCapsiate
DescriptionCapsiate, also known as capsiic acid, 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. Capsiate has been detected, but not quantified in, several different foods, such as orange bell peppers (Capsicum annuum), red bell peppers (Capsicum annuum), yellow bell peppers (Capsicum annuum), italian sweet red peppers (Capsicum annuum), and green bell peppers (Capsicum annuum). This could make capsiate a potential biomarker for the consumption of these foods. Capsiate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Capsiate.
Structure
Data?1563862617
Synonyms
ValueSource
Vanillyl (6E)-8-methylnon-6-enoateChEBI
Vanillyl (6E)-8-methylnon-6-enoic acidGenerator
Capsiic acidGenerator
4-Hydroxy-3-methoxybenzyl 8-methyl-6-nonenoateHMDB
DihydrocapsiateMeSH, HMDB
Nonanoic acid, 8-methyl-, (4-hydroxy-3-methoxyphenyl)methyl esterMeSH
Chemical FormulaC18H26O4
Average Molecular Weight306.3966
Monoisotopic Molecular Weight306.18310932
IUPAC Name(4-hydroxy-3-methoxyphenyl)methyl (6E)-8-methylnon-6-enoate
Traditional Name(4-hydroxy-3-methoxyphenyl)methyl (6E)-8-methylnon-6-enoate
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(COC(=O)CCCC\C=C\C(C)C)=C1
InChI Identifier
InChI=1S/C18H26O4/c1-14(2)8-6-4-5-7-9-18(20)22-13-15-10-11-16(19)17(12-15)21-3/h6,8,10-12,14,19H,4-5,7,9,13H2,1-3H3/b8-6+
InChI KeyZICNYIDDNJYKCP-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
  • Benzyloxycarbonyl
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Alkyl aryl ether
  • Fatty acyl
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point421.27 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.53 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.515 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP4.5ALOGPS
logP4.48ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.91ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity88.37 m³·mol⁻¹ChemAxon
Polarizability35.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+175.89831661259
DarkChem[M-H]-173.57631661259
DeepCCS[M+H]+192.78830932474
DeepCCS[M-H]-190.4330932474
DeepCCS[M-2H]-223.31730932474
DeepCCS[M+Na]+198.88130932474
AllCCS[M+H]+176.832859911
AllCCS[M+H-H2O]+173.832859911
AllCCS[M+NH4]+179.632859911
AllCCS[M+Na]+180.432859911
AllCCS[M-H]-178.532859911
AllCCS[M+Na-2H]-179.232859911
AllCCS[M+HCOO]-180.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CapsiateCOC1=C(O)C=CC(COC(=O)CCCC\C=C\C(C)C)=C13690.2Standard polar33892256
CapsiateCOC1=C(O)C=CC(COC(=O)CCCC\C=C\C(C)C)=C12283.3Standard non polar33892256
CapsiateCOC1=C(O)C=CC(COC(=O)CCCC\C=C\C(C)C)=C12301.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Capsiate,1TMS,isomer #1COC1=CC(COC(=O)CCCC/C=C/C(C)C)=CC=C1O[Si](C)(C)C2422.4Semi standard non polar33892256
Capsiate,1TBDMS,isomer #1COC1=CC(COC(=O)CCCC/C=C/C(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2658.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Capsiate GC-MS (Non-derivatized) - 70eV, Positivesplash10-055u-5920000000-60d000d43b1f9096c1922017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Capsiate GC-MS (1 TMS) - 70eV, Positivesplash10-01t9-7965000000-9061c1d933cf836a3a4c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Capsiate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Capsiate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsiate 10V, Positive-QTOFsplash10-0a4r-0915000000-d19997b754042e7519cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsiate 20V, Positive-QTOFsplash10-000i-2900000000-f589d122afe9d7c95df22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsiate 40V, Positive-QTOFsplash10-052r-8900000000-45c9e4b9e1a49bb886d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsiate 10V, Negative-QTOFsplash10-0pb9-0908000000-d0650030a37b0e1edd5f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsiate 20V, Negative-QTOFsplash10-0uxr-0901000000-41bf8df5d7f9f5c0de1d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsiate 40V, Negative-QTOFsplash10-0k9f-3900000000-ea96ed7aae0cb04b66492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsiate 10V, Negative-QTOFsplash10-014i-0900000000-3af65de2869b973825d62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsiate 20V, Negative-QTOFsplash10-0v6r-1900000000-973956f425d4207c35592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsiate 40V, Negative-QTOFsplash10-0udi-3912000000-fa5e9b2552f99de0f2772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsiate 10V, Positive-QTOFsplash10-052r-0900000000-7fa0654d4ef4c85920a22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsiate 20V, Positive-QTOFsplash10-0a4r-1900000000-f6058625f5a778bf72992021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsiate 40V, Positive-QTOFsplash10-052r-3900000000-97d9169adb4f26f974b82021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013333
KNApSAcK IDC00053980
Chemspider ID8015237
KEGG Compound IDC20203
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9839519
PDB IDNot Available
ChEBI ID134190
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1679241
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Macho A, Sancho R, Minassi A, Appendino G, Lawen A, Munoz E: Involvement of reactive oxygen species in capsaicinoid-induced apoptosis in transformed cells. Free Radic Res. 2003 Jun;37(6):611-9. [PubMed:12868488 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .