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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:33:01 UTC
Update Date2021-10-13 06:03:32 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 odorless and a bland tasting compound. 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 Capsaicin (PMID:6202305 ).
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
N-VanillylnonanamideMeSH
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point124.00 to 128.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point492.00 to 493.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP3.202 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP10(4.05) g/LALOGPS
logP10(3.82) g/LChemAxon
logS10(-4.1) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+174.49131661259
DarkChem[M-H]-173.47831661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nonivamide,1TMS,#1CCCCCCCCC(=O)NCC1=CC=C(O[Si](C)(C)C)C(OC)=C12604.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Nonivamide,1TMS,#2CCCCCCCCC(=O)N(CC1=CC=C(O)C(OC)=C1)[Si](C)(C)C2458.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Nonivamide,1TBDMS,#1CCCCCCCCC(=O)NCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C12862.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Nonivamide,1TBDMS,#2CCCCCCCCC(=O)N(CC1=CC=C(O)C(OC)=C1)[Si](C)(C)C(C)(C)C2704.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Nonivamide EI-B (Non-derivatized)splash10-000i-0900000000-6f2029bbeaa0669340a02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Nonivamide EI-B (Non-derivatized)splash10-000i-0900000000-6f2029bbeaa0669340a02018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nonivamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-7920000000-cd906e25cbbe33ac1d902017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nonivamide GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-9483000000-60843c2f864991f329cf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nonivamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Nonivamide , positive-QTOFsplash10-000i-3900000000-0e1c18bae04636c6203e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nonivamide LC-ESI-QFT , positive-QTOFsplash10-000i-0900000000-8458eb835ff534a3139b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nonivamide 90V, Positive-QTOFsplash10-0076-9700000000-2a59478a1e48f1fb682f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nonivamide 75V, Positive-QTOFsplash10-0079-3900000000-d2e771312ae8b15c0eb82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nonivamide 15V, Negative-QTOFsplash10-0a4i-0900000000-36905c7dcb78a52a01de2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nonivamide 30V, Negative-QTOFsplash10-0a4i-0900000000-d045e39cc84e57890cb72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nonivamide 60V, Positive-QTOFsplash10-000i-1900000000-9648421277a046c73ead2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nonivamide 45V, Positive-QTOFsplash10-000i-0900000000-13d27fcfbe7bec7313742021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nonivamide 15V, Positive-QTOFsplash10-000i-0900000000-7d5ea4adf9a443e85cfa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nonivamide 30V, Positive-QTOFsplash10-000i-0900000000-89b62e29d94cae1578482021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nonivamide 60V, Negative-QTOFsplash10-0a4i-0900000000-bea368f052fc74b2e53a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nonivamide 45V, Negative-QTOFsplash10-0a4i-0900000000-831a7310ced159f2faad2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nonivamide 35V, Positive-QTOFsplash10-000i-0900000000-c1069887607603f3585a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonivamide 10V, Positive-QTOFsplash10-0006-0950000000-67e561ae29f2afb297782015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonivamide 20V, Positive-QTOFsplash10-000i-1900000000-22d461bcbb8449562ea62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonivamide 40V, Positive-QTOFsplash10-000i-5900000000-0d2b494b9af632d043d12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonivamide 10V, Negative-QTOFsplash10-0006-0390000000-ec9c31843d3afbcd09392015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonivamide 20V, Negative-QTOFsplash10-0k9f-0940000000-709a4f4d48c16fcf87472015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonivamide 40V, Negative-QTOFsplash10-052o-7900000000-f49d6bc681a0fe7bb4ac2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonivamide 10V, Negative-QTOFsplash10-0a4l-0940000000-5c718c68d8c6654171322021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonivamide 20V, Negative-QTOFsplash10-0a4i-4900000000-326a985c62c83a12039a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonivamide 40V, Negative-QTOFsplash10-0006-9100000000-d2ec78d0636bf28260d42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonivamide 10V, Positive-QTOFsplash10-000l-0950000000-d3e4a41c8ad8728aabf12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonivamide 20V, Positive-QTOFsplash10-000i-0900000000-1c17ee8d9e776e99b7222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonivamide 40V, Positive-QTOFsplash10-000i-2900000000-1c8124772393ecc8fd3d2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 IDC00054000
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 IDNot Available
Good Scents IDrw1033291
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Skofitsch G, Donnerer J, Lembeck F: Comparison of nonivamide and capsaicin with regard to their pharmacokinetics and effects on sensory neurons. Arzneimittelforschung. 1984;34(2):154-6. [PubMed:6202305 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .