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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:33:01 UTC
Update Date2020-02-26 21:44:34 UTC
HMDB IDHMDB0029846
Secondary Accession Numbers
  • HMDB29846
Metabolite Identification
Common NameNonivamide
DescriptionNonivamide, also known as pseudocapsaicin or hansaplast, 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. Nonivamide is an extremely weak basic (essentially neutral) compound (based on its pKa). Nonivamide is a bland and odorless tasting compound. Outside of the human body, Nonivamide is found, on average, in the highest concentration within a few different foods, such as yellow bell peppers, red bell peppers, and pepper (c. frutescens) and in a lower concentration in pepper (c. annuum), orange bell peppers, and green bell peppers. Nonivamide has also been detected, but not quantified in, herbs and spices. This could make nonivamide a potential biomarker for the consumption of these foods. Limited information is available on pharmacokinetics and metabolism of nonivamide . Agonism of the VR1 (TRPV1) (vanilloid) receptor by Nonivamide was demonstrated to induce the release of Ca2+ from the endoplasmic reticulum (ER) of human lung cells, producing ER stress and cell death . The cardiovascular effects are partly explained by substance P release. Administered intraperitoneally, the LD50 in rats was measured to be about 90 mg/kg. Nonivamide has been shown to stimulate afferent neurons with about half the potency of .
Structure
Data?1582753474
Synonyms
ValueSource
Hydroxymethoxybenzyl pelargonamideChEBI
N-Nonanoyl vanillylamideChEBI
N-VanillylnonamideChEBI
N-VanillylpelargonamideChEBI
Pelargonyl vanillylamideChEBI
PseudocapsaicinChEBI
Vanillyl-N-nonylamideChEBI
Nonanoic acid vanillylamideKegg
HansaplastKegg
Nonanoate vanillylamideGenerator
4-Hydroxy-3-methoxy-N-(1-oxononyl)-benzamideHMDB
FEMA 2787HMDB
HH 50HMDB
N-((4-Hydroxy-3-methoxyphenyl)methyl)-nonanamideHMDB
N-((4-Hydroxy-3-methoxyphenyl)methyl)nonanamideHMDB
N-((Hydroxy-3-methoxyphenyl)methyl)4-nonanamideHMDB
N-(4-Hydroxy-3-methoxybenzyl)nonanamideHMDB
N-Vanillyl nonanamideHMDB
N-Vanillyl-nonanamideHMDB
N-Vanillylnonanamide, 8ciHMDB
N-[(4-Hydroxy-3-methoxyphenyl)methyl]-nonanamideHMDB
N-[(4-Hydroxy-3-methoxyphenyl)methyl]nonanamide, 9ciHMDB
Nonanoyl 4-hydroxy-3-methoxybenzylamideHMDB
Nonanoyl vanillylamideHMDB
Nonoyl vanillylamideHMDB
Nonylic acid vanillylamideHMDB
NonylvanylamideHMDB
Pelargonic acid vanillylamideHMDB
Pelargonoyl vanillylamideHMDB
PSVAHMDB
Synthetic capsaicinHMDB
Vanillyl N-nonoylamideHMDB
Vanillyl pelargonic amideHMDB
VanillylnonanamideMeSH
N-VanillylnonanamideMeSH
Chemical FormulaC17H27NO3
Average Molecular Weight293.4012
Monoisotopic Molecular Weight293.199093735
IUPAC NameN-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
Traditional Namenonivamide
CAS Registry Number2444-46-4
SMILES
CCCCCCCCC(=O)NCC1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20)
InChI KeyRGOVYLWUIBMPGK-UHFFFAOYSA-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
  • Carboximidic acid
  • Carboximidic acid derivative
  • Ether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP4.05ALOGPS
logP3.82ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.93ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.56 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity84.65 m³·mol⁻¹ChemAxon
Polarizability35.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0900000000-6f2029bbeaa0669340a0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0900000000-6f2029bbeaa0669340a0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-7920000000-cd906e25cbbe33ac1d90Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-9483000000-60843c2f864991f329cfSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-3900000000-0e1c18bae04636c6203eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0900000000-8458eb835ff534a3139bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0950000000-67e561ae29f2afb29778Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-22d461bcbb8449562ea6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-5900000000-0d2b494b9af632d043d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0390000000-ec9c31843d3afbcd0939Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0k9f-0940000000-709a4f4d48c16fcf8747Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052o-7900000000-f49d6bc681a0fe7bb4acSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDDB11324
Phenol Explorer Compound IDNot Available
FooDB IDFDB001066
KNApSAcK IDNot Available
Chemspider ID2891
KEGG Compound IDNot Available
BioCyc IDCPD-9183
BiGG IDNot Available
Wikipedia LinkNonivamide
METLIN IDNot Available
PubChem Compound2998
PDB IDNot Available
ChEBI ID46936
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .