Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for Vanillylamine (HMDB12309)

Blood
Urine

Record Information

Version

3.5

Creation Date

2009-04-06 10:22:44 -0600

Update Date

2013-05-07 13:44:47 -0600

HMDB ID

HMDB12309

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Vanillylamine

Description

Vanillylamine is prepared by reacting vanillin with hydroxylamine or the salts thereof in the presence of an organic salt, which may optionally be produced in situ, wherein the reaction is carried out in an inorganic or organic acid as diluent, and subsequently hydrogenating the resulting vanillyloxime with hydrogen in the presence of a suitable catalyst and an organic and/or inorganic acid.It inhibits microsomal enzyme function; RN given refers to parent cpd. Vanillylamine is a component of capsaicin.In Pseudomonas fluorescens B56 under growing conditions, the cells metabolized vanillylamine to vanillin, and vanillin to vanillic acid and a small amount of vanillyl alcohol. Under non-growing conditions, the cells produced vanillin, vanillic acid and protocatechuic acid from vanillylamine, and vanillic acid supplied to the medium was converted to protocatechuic acid. It is thus suggested that vanillylamine is metabolized to vanillic acid through vanillin by Pseudomonas fluorescens B56 in a rich medium, however, in a starving medium, the bacterial strain further metabolizes vanillic acid to protocatechuic acid. The vanillylamine metabolic activity was slowly induced by the substrate.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

(3-Methoxy-4-hydroxyphenyl)methylamine
(4-Hydroxy-3-methoxyphenyl)methanamine
3-Methoxy-4-hydroxybenzylamine
4-Aminomethyl-2-methoxy-phenol
4-Hydroxy-3-methoxybenzylamine
a-Amino-2-methoxy-p-Cresol
alpha-Amino-2-methoxy-p-Cresol

Chemical Formula

C₈H₁₁NO₂

Average Molecular Weight

153.1784

Monoisotopic Molecular Weight

153.078978601

IUPAC Name

4-(aminomethyl)-2-methoxyphenol

Traditional IUPAC Name

vanillylamine

CAS Registry Number

1196-92-5

SMILES

COC1=CC(CN)=CC=C1O

InChI Identifier

InChI=1S/C8H11NO2/c1-11-8-4-6(5-9)2-3-7(8)10/h2-4,10H,5,9H2,1H3

InChI Key

WRPWWVNUCXQDQV-UHFFFAOYSA-N

Chemical Taxonomy

Kingdom

Organic Compounds

Super Class

Aromatic Homomonocyclic Compounds

Class

Phenols and Derivatives

Sub Class

Methoxyphenols and Derivatives

Other Descriptors

Aromatic Homomonocyclic Compounds
aralkylamine(ChEBI)

Substituents

Alkyl Aryl Ether
Anisole
Phenylmethylamine
Primary Aliphatic Amine (Alkylamine)

Direct Parent

Methoxyphenols and Derivatives

Ontology

Status

Expected and Not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-0.37	Predicted by ALOGPS

Predicted Properties

Property	Value	Source
Water Solubility	16.1 g/L	ALOGPS
LogP	-0.37	ALOGPS
LogP	0.2	ChemAxon
LogS	-0.98	ALOGPS
pKa (strongest acidic)	10.1	ChemAxon
pKa (strongest basic)	9.26	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	55.48 A²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.98	ChemAxon
Polarizability	16.16	ChemAxon
Formal Charge	0	ChemAxon
Physiological Charge	1	ChemAxon