ChemFOnt: Showing chemical card for N-Vanillyl-N-Nonamide (CFc000333574)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:47 UTC

Chemfont ID

CFc000333574

Molecule Identification

Common Name

N-Vanillyl-N-Nonamide

Definition

Nonivamide, also known as vanillyl-N-nonylamide or hydroxymethoxybenzyl pelargonamide, is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Nonivamide is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Nonivamide is a bland and odorless tasting compound and can be found in a number of food items such as herbs and spices, pepper (c. annuum), yellow bell pepper, and orange bell pepper, which makes nonivamide a potential biomarker for the consumption of these food products. Nonivamide is used (under the name PAVA) as the payload in "less-lethal munitions" such as the Fabrique Nationale Herstal FN 303 or as the active ingredient in most pepper sprays – in both applications, the idea is to temporarily incapacitate people so that they can either be detained prior to arrest or deterred from acts of violence toward law-enforcement personnel or third parties (such as rioting or other group violence) .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Hydroxymethoxybenzyl pelargonamide	ChEBI
N-Nonanoyl vanillylamide	ChEBI
N-Vanillylnonamide	ChEBI
N-Vanillylpelargonamide	ChEBI
Pelargonyl vanillylamide	ChEBI
Pseudocapsaicin	ChEBI
Vanillyl-N-nonylamide	ChEBI
Nonanoic acid vanillylamide	Kegg
Hansaplast	Kegg
Nonanoate vanillylamide	Generator
4-Hydroxy-3-methoxy-N-(1-oxononyl)-benzamide	HMDB
FEMA 2787	HMDB
HH 50	HMDB
N-((4-Hydroxy-3-methoxyphenyl)methyl)-nonanamide	HMDB
N-((4-Hydroxy-3-methoxyphenyl)methyl)nonanamide	HMDB
N-((Hydroxy-3-methoxyphenyl)methyl)4-nonanamide	HMDB
N-(4-Hydroxy-3-methoxybenzyl)nonanamide	HMDB
N-Vanillyl nonanamide	HMDB
N-Vanillyl-nonanamide	HMDB
N-Vanillylnonanamide, 8ci	HMDB
N-[(4-Hydroxy-3-methoxyphenyl)methyl]-nonanamide	HMDB
N-[(4-Hydroxy-3-methoxyphenyl)methyl]nonanamide, 9ci	HMDB
Nonanoyl 4-hydroxy-3-methoxybenzylamide	HMDB
Nonanoyl vanillylamide	HMDB
Nonoyl vanillylamide	HMDB
Nonylic acid vanillylamide	HMDB
Nonylvanylamide	HMDB
Pelargonic acid vanillylamide	HMDB
Pelargonoyl vanillylamide	HMDB
PSVA	HMDB
Synthetic capsaicin	HMDB
Vanillyl N-nonoylamide	HMDB
Vanillyl pelargonic amide	HMDB
N-Vanillylnonanamide	MeSH
Vanillylnonanamide	MeSH

Chemical Formula

C₁₇H₂₇NO₃

Average Molecular Weight

293.4012

Monoisotopic Molecular Weight

293.199093735

IUPAC Name

N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide

Traditional Name

nonivamide

CAS Registry Number

2444-46-4

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 Key

RGOVYLWUIBMPGK-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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:46936 )
capsaicinoid (CHEBI:46936 )
an alkaloid (CPD-9183 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0029846)

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.023 g/L	ALOGPS
logP	4.05	ALOGPS
logP	3.82	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	84.65 m³·mol⁻¹	ChemAxon
Polarizability	35.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon