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Human Metabolome Database Version 3.5

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Showing metabocard for Vanillactic acid (HMDB00913)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:34 -0700
HMDB ID HMDB00913
Secondary Accession Numbers None
Metabolite Identification
Common Name Vanillactic acid
Description Vanillactic acid is an acidic catecholamine metabolite present in normal human urine (PMID 7524950 Link_out), in normal human CSF (PMID 7914240 Link_out), and increased in the CSF of newborns with neonatal epileptic encephalopathy mimicking aromatic L-amino acid decarboxylase deficiency (PMID 12200739 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3-(3-Methoxy-4-hydroxyphenyl)lactate
  2. 3-(3-Methoxy-4-hydroxyphenyl)lactic acid
  3. 3-(4-Hydroxy-3-methoxyphenyl)-Lactate
  4. 3-(4-Hydroxy-3-methoxyphenyl)-Lactic acid
  5. 3-(4-Hydroxy-3-methoxyphenyl)lactate
  6. 3-(4-Hydroxy-3-methoxyphenyl)lactic acid
  7. 3-Methoxy-4-hydroxyphenyllactate
  8. 3-Methoxy-4-hydroxyphenyllactic acid
  9. 4-Hydroxy-3-methoxyphenyllactic acid
  10. b-(4-Hydroxy-3-methoxyphenyl)lactate
  11. b-(4-Hydroxy-3-methoxyphenyl)lactic acid
  12. beta-(4-Hydroxy-3-methoxyphenyl)lactate
  13. beta-(4-Hydroxy-3-methoxyphenyl)lactic acid
  14. Vanillactate
  15. Vanillactic acid
  16. Vanillyllactate
  17. Vanillyllactic acid
  18. VLA
Chemical Formula C10H12O5
Average Molecular Weight 212.1993
Monoisotopic Molecular Weight 212.068473494
IUPAC Name 2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propanoic acid
Traditional IUPAC Name 2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propanoic acid
CAS Registry Number 2475-56-1
SMILES COC1=CC(CC(O)C(O)=O)=CC=C1O
InChI Identifier InChI=1S/C10H12O5/c1-15-9-5-6(2-3-7(9)11)4-8(12)10(13)14/h2-3,5,8,11-12H,4H2,1H3,(H,13,14)
InChI Key SVYIZYRTOYHQRE-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Benzyl Alcohols and Derivatives
Sub Class Phenylpyruvic Acid Derivatives
Other Descriptors
  • Organic Compounds
  • Tyrosols and Derivatives
  • a small molecule(Cyc)
Substituents
  • Alkyl Aryl Ether
  • Alpha Hydroxy Acid
  • Anisole
  • Carboxylic Acid
  • Methoxyphenol
  • Phenol
  • Phenol Derivative
  • Secondary Alcohol
Direct Parent Phenylpyruvic Acid 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 4.3 g/L ALOGPS
LogP 1.08 ALOGPS
LogP 0.72 ChemAxon
LogS -1.69 ALOGPS
pKa (strongest acidic) 3.37 ChemAxon
pKa (strongest basic) -3.8 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 86.99 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 51.9 ChemAxon
Polarizability 20.58 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and Quantified
Article_icon
0.0933 (0.00-0.187) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID 972 Link_out
FoodDB ID FDB022315
KNApSAcK ID Not Available
Chemspider ID 141152 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link VLA Link_out
NuGOwiki Link HMDB00913 Link_out
Metagene Link HMDB00913 Link_out
METLIN ID 5868 Link_out
PubChem Compound 160637 Link_out
PDB ID Not Available
ChEBI ID 1240674 Link_out
References
Synthesis Reference Wong, Henry N. C.; Xu, Zun Le; Chang, Hson Mou; Lee, Chi Ming. Compounds from Danshen. 6. A modified synthesis of (±)-b-aryllactic acids. Synthesis (1992), (8), 793-7.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Javors MA, Bowden CL, Maas JW: 3-methoxy-4-hydroxyphenylglycol, 5-hydroxyindoleacetic acid, and homovanillic acid in human cerebrospinal fluid. Storage and measurement by reversed-phase high-performance liquid chromatography and coulometric detection using 3-methoxy-4-hydroxyphenyllactic acid as an internal standard. J Chromatogr. 1984 Dec 12;336(2):259-69. Pubmed: 6085084 Link_out
  2. 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
  3. Ikeda H, Matsuyama S, Suzuki N, Takahashi A, Kuroiwa M: 3,4-dihydroxyphenylalanine (DOPA) decarboxylase deficiency and resultant high levels of plasma DOPA and dopamine in unfavorable neuroblastoma. Hypertens Res. 1995 Jun;18 Suppl 1:S209-10. Pubmed: 8529065 Link_out
  4. Kinoshita Y, Yamada S, Haraguchi K, Takayanagi T, Mori Y, Takahashi T, Haruki E: Determination of vanillylmandelic acid, vanillactic acid, and homovanillic acid in dried urine on filter-paper discs by high-performance liquid chromatography with coulometric electrochemical detection for neuroblastoma screening. Clin Chem. 1988 Nov;34(11):2228-30. Pubmed: 3180413 Link_out
  5. Muskiet FA, Fremouw-Ottevangers DC, van der Meulen J, Wolthers BG, de Vries JA: Determination of some L-3,4-dihydroxyphenylalanine and dopamine metabolites in urine by means of mass fragmentography. Clin Chem. 1978 Jan;24(1):122-7. Pubmed: 73430 Link_out
  6. Jouve J, Bakri D, Herault J, Muh JP: Determination of urinary vanillactic acid and plasma dihydroxyphenylalanine as markers of non-secreting neuroblastoma by high-performance liquid chromatography with electrochemical detection. J Chromatogr. 1991 Jul 5;567(2):331-41. Pubmed: 1939466 Link_out
  7. Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10. Pubmed: 1281049 Link_out
  8. Mashige F, Ohkubo A, Matsushima Y, Takano M, Tsuchiya E, Kanazawa H, Nagata Y, Takai N, Shinozuka N, Sakuma I: High-performance liquid chromatographic determination of catecholamine metabolites and 5-hydroxyindoleacetic acid in human urine using a mixed-mode column and an eight-channel electrode electrochemical detector. J Chromatogr B Biomed Appl. 1994 Aug 5;658(1):63-8. Pubmed: 7524950 Link_out
  9. Tuchman M, Stoeckeler JS: Conjugated versus "free" acidic metabolites of catecholamines in random urine samples: significance for the diagnosis of neuroblastoma. Pediatr Res. 1988 Jun;23(6):576-9. Pubmed: 3393388 Link_out