Record Information
Version1.0
Creation date2010-04-08 22:04:49 UTC
Update date2018-05-28 22:37:22 UTC
Primary IDFDB001066
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNonivamide
DescriptionAlkaloid from Capsicum subspecies Flavouring ingredient Nonivamide is an organic compound and a capsaicinoid. It is an amide of pelargonic acid and vanillylamine. It is present in chili peppers, but is commonly manufactured synthetically. It is more heat-stable than capsaicin. Nonivamide is found in many foods, some of which are yellow bell pepper, pepper (c. frutescens), orange bell pepper, and herbs and spices.
CAS Number2444-46-4
Structure
Thumb
Synonyms
SynonymSource
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
Benzamide, 4-hydroxy-3-methoxy-N-(1-oxononyl)-biospider
N-[(4-Hydroxy-3-methoxyphenyl)methyl]nonanamide, 9CIdb_source
N-Vanillylnonanamide, 8CIdb_source
Nonanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-biospider
Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-biospider
Nonanamide, N-vanillyl-biospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC17H27NO3
IUPAC nameN-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
InChI IdentifierInChI=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
Isomeric SMILESCCCCCCCCC(=O)NCC1=CC(OC)=C(O)C=C1
Average Molecular Weight293.4012
Monoisotopic Molecular Weight293.199093735
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 69.59%; H 9.27%; N 4.77%; O 16.36%DFC
Melting PointNot Available
Boiling PointBp0.05 200-210°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0900000000-6f2029bbeaa0669340a0View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0900000000-6f2029bbeaa0669340a0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-7920000000-cd906e25cbbe33ac1d90View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-9483000000-60843c2f864991f329cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-3900000000-0e1c18bae04636c6203eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0900000000-8458eb835ff534a3139bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0950000000-67e561ae29f2afb29778View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-22d461bcbb8449562ea6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-5900000000-0d2b494b9af632d043d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0390000000-ec9c31843d3afbcd0939View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0k9f-0940000000-709a4f4d48c16fcf8747View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052o-7900000000-f49d6bc681a0fe7bb4acView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID2891
ChEMBL IDCHEMBL75124
KEGG Compound IDNot Available
Pubchem Compound ID2998
Pubchem Substance IDNot Available
ChEBI ID46936
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29846
CRC / DFC (Dictionary of Food Compounds) IDHGT21-K:BRG13-H
EAFUS ID2700
Dr. Duke IDNONIVAMIDE|NONANOIC-ACID-VANILLYLAMIDE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1033291
SuperScent IDNot Available
Wikipedia IDNonivamide
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSBRG13-H:BRG13-H
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bland
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).