Human Metabolome Database Version 3.5

Showing metabocard for Vanillylamine (HMDB12309)

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 Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (3-Methoxy-4-hydroxyphenyl)methylamine
  2. (4-Hydroxy-3-methoxyphenyl)methanamine
  3. 3-Methoxy-4-hydroxybenzylamine
  4. 4-Aminomethyl-2-methoxy-phenol
  5. 4-Hydroxy-3-methoxybenzylamine
  6. a-Amino-2-methoxy-p-Cresol
  7. 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
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB028931
KNApSAcK ID Not Available
Chemspider ID 64127 Link_out
KEGG Compound ID C16666 Link_out
BioCyc ID CPD-9327 Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12309 Link_out
Metagene Link HMDB12309 Link_out
METLIN ID Not Available
PubChem Compound 70966 Link_out
PDB ID Not Available
ChEBI ID 46958 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available