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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-02-24 09:13:55 UTC
Update Date2020-02-26 21:35:43 UTC
HMDB IDHMDB0011716
Secondary Accession Numbers
  • HMDB11716
Metabolite Identification
Common NameN-Acetylvanilalanine
DescriptionN-Acetylvanilalanine belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Acetylvanilalanine is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetylvanilalanine has been linked to the inborn metabolic disorders including aromatic l-amino acid decarboxylase deficiency.
Structure
Data?1582752943
Synonyms
ValueSource
N-Acetyl-vanilalanineHMDB
3-(4-Hydroxy-3-methoxyphenyl)-2-[(1-hydroxyethylidene)amino]propanoateGenerator
Chemical FormulaC12H15NO5
Average Molecular Weight253.2512
Monoisotopic Molecular Weight253.095022595
IUPAC Name2-acetamido-3-(4-hydroxy-3-methoxyphenyl)propanoic acid
Traditional Name2-acetamido-3-(4-hydroxy-3-methoxyphenyl)propanoic acid
CAS Registry NumberNot 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 KeyUKDKTHYZLXZOSS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentTyrosine and derivatives
Alternative Parents
Substituents
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.29 g/LALOGPS
logP1.25ALOGPS
logP0.44ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.48ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.86 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity63 m³·mol⁻¹ChemAxon
Polarizability25.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9530000000-88e789bd50bcb7d1ca90Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9014000000-dda2c49be0e1b55e83daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0290000000-7593dceb7a0c284d48dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07vr-1970000000-4df59618dbc09ea1fe41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avr-4900000000-2639c0e6bef8583c7b1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0190000000-73b12fcdc611e96a0765Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0rkc-5790000000-b29af3d062fafe86098dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9500000000-057477279b85a32a5bdaSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified10 +/- 2 umol/mmol creatinineInfant (0-1 year old)MaleAromatic L-amino acid decarboxylase deficiency details
Associated Disorders and Diseases
Disease References
Aromatic L-amino acid decarboxylase deficiency
  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 ]
Associated OMIM IDs
  • 608643 (Aromatic L-amino acid decarboxylase deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028401
KNApSAcK IDNot Available
Chemspider ID15185955
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12681285
PDB IDNot Available
ChEBI ID88403
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot 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 ]