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Human Metabolome Database Version 3.5

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Showing metabocard for N-Acetylvanilalanine (HMDB11716)

Record Information
Version 3.5
Creation Date 2009-02-24 02:13:55 -0700
Update Date 2013-02-08 17:27:13 -0700
HMDB ID HMDB11716
Secondary Accession Numbers None
Metabolite Identification
Common Name N-Acetylvanilalanine
Description N-acetylvanilalanine is a catecholamine metabolite. Its accumulation is indicative of aromatic L-amino acid decarboxylase deficiency (PMID: 16288991 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. N-Acetyl-vanilalanine
Chemical Formula C12H15NO5
Average Molecular Weight 253.2512
Monoisotopic Molecular Weight 253.095022595
IUPAC Name 2-acetamido-3-(4-hydroxy-3-methoxyphenyl)propanoic acid
Traditional IUPAC Name 2-acetamido-3-(4-hydroxy-3-methoxyphenyl)propanoic acid
CAS Registry Number Not Available
SMILES COC1=CC(CC(NC(C)=O)C(O)=O)=CC=C1O
InChI Identifier InChI=1S/C12H15NO5/c1-7(14)13-9(12(16)17)5-8-3-4-10(15)11(6-8)18-2/h3-4,6,9,15H,5H2,1-2H3,(H,13,14)(H,16,17)
InChI Key UKDKTHYZLXZOSS-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
Substituents
  • Alkyl Aryl Ether
  • Amphetamine Or Derivative
  • Anisole
  • Carboxamide Group
  • Carboxylic Acid
  • Catecholamine
  • Methoxyphenol
  • Phenol
  • Phenol Derivative
  • Secondary Carboxylic Acid Amide
Direct Parent N-acyl-alpha Amino Acids and Derivatives
Ontology
Status Detected and 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 Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 2.29 g/L ALOGPS
LogP 1.25 ALOGPS
LogP 0.44 ChemAxon
LogS -2.04 ALOGPS
pKa (strongest acidic) 3.48 ChemAxon
pKa (strongest basic) -1.5 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 95.86 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 63 ChemAxon
Polarizability 25.07 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
10 +/- 2 umol/mmol creatinine Infant (0-1 year old) Male Aromatic L-amino acid decarboxylase deficiency Not Available
Associated Disorders and Diseases
Disease References
Aromatic L-amino acid decarboxylase deficiency
  • Abdenur JE, Abeling N, Specola N, Jorge L, Schenone AB, van Cruchten AC, Chamoles NA: Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Mol Genet Metab. 2006 Jan;87(1):48-53. Epub 2005 Nov 9. Pubmed: 16288991 Link_out
    Associated OMIM IDs
    • 107930 Link_out (Aromatic L-amino acid decarboxylase deficiency)
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB028401
    KNApSAcK ID Not Available
    Chemspider ID 15185955 Link_out
    KEGG Compound ID Not Available
    BioCyc ID Not Available
    BiGG ID Not Available
    Wikipedia Link Not Available
    NuGOwiki Link HMDB11716 Link_out
    Metagene Link HMDB11716 Link_out
    METLIN ID Not Available
    PubChem Compound 12681285 Link_out
    PDB ID Not Available
    ChEBI ID Not Available
    References
    Synthesis Reference Not Available
    Material Safety Data Sheet (MSDS) Not Available
    General References
    1. Abdenur JE, Abeling N, Specola N, Jorge L, Schenone AB, van Cruchten AC, Chamoles NA: Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Mol Genet Metab. 2006 Jan;87(1):48-53. Epub 2005 Nov 9. Pubmed: 16288991 Link_out