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Human Metabolome Database Version 3.5

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Showing metabocard for Vanillylmandelic acid (HMDB00291)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:15 -0700
HMDB ID HMDB00291
Secondary Accession Numbers None
Metabolite Identification
Common Name Vanillylmandelic acid
Description Vanillylmandelic acid is one of the products of the catabolism of catecholamines (epinephrine, norepinephrine and dopamine). High levels of vanillylmandelic acid can indicate an adrenal gland tumor (pheochromocytoma) or another type of tumor that produces catecholamines. (WebMD).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (4-Hydroxy-3-methoxyphenyl)glycolate
  2. (4-Hydroxy-3-methoxyphenyl)glycolic acid
  3. 3-Methoxy-4-hydroxy-mandelic acid
  4. 3-Methoxy-4-hydroxymandelate
  5. 3-Methoxy-4-hydroxymandelic acid
  6. 3-Methoxy-4-hydroxyphenylhydroxyacetate
  7. 3-Methoxy-4-hydroxyphenylhydroxyacetic acid
  8. 4'-Hydroxy-3'-methoxymandelate
  9. 4'-Hydroxy-3'-methoxymandelic acid
  10. 4-Hydroxy 3-methoxymandelic acid
  11. 4-Hydroxy-3-methoxy-DL-mandelate
  12. 4-Hydroxy-3-methoxy-DL-mandelic acid
  13. 4-Hydroxy-3-methoxy-Mandelate
  14. 4-Hydroxy-3-methoxy-Mandelic acid
  15. 4-Hydroxy-3-methoxymandelate
  16. 4-Hydroxy-3-methoxymandelic acid
  17. DL-3-Methoxy-4-hydroxymandelate
  18. DL-3-Methoxy-4-hydroxymandelic acid
  19. DL-4-Hydroxy-3-methoxymandelate
  20. DL-4-Hydroxy-3-methoxymandelic acid
  21. DL-vanillomandelate
  22. DL-vanillomandelic acid
  23. DL-vanillylmandelate
  24. DL-vanillylmandelic acid
  25. HMMA
  26. Hydroxymethoxymandelic acid
  27. Lopac-H-0131
  28. Vainillylmandelic acid
  29. Vanillinmandelate
  30. Vanillinmandelic acid
  31. Vanillomandelate
  32. Vanillomandelic acid
  33. Vanillyl-mandelic acid
  34. Vanillylmandelate
  35. Vanillylmandellic acid
  36. Vanillymandelic acid
  37. Vanilmandelate
  38. Vanilmandelic acid
  39. Vanilylmandelic acid
  40. Vanyl-mandelic acid
  41. Vanylmandelic acid
  42. VMA
Chemical Formula C9H10O5
Average Molecular Weight 198.1727
Monoisotopic Molecular Weight 198.05282343
IUPAC Name (2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
Traditional IUPAC Name (S)-hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid
CAS Registry Number 55-10-7
SMILES COC1=C(O)C=CC(=C1)[C@H](O)C(O)=O
InChI Identifier InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)/t8-/m0/s1
InChI Key CGQCWMIAEPEHNQ-QMMMGPOBSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenols and Derivatives
Sub Class Tyrosols and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
Substituents
  • Alkyl Aryl Ether
  • Alpha Hydroxy Acid
  • Anisole
  • Benzyl Alcohol Derivative
  • Carboxylic Acid
  • Methoxyphenol
  • Phenylacetate
  • Secondary Alcohol
Direct Parent Tyrosols and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 132 - 134 °C 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 5.16 g/L ALOGPS
LogP 0.94 ALOGPS
LogP 0.43 ChemAxon
LogS -1.58 ALOGPS
pKa (strongest acidic) 3.11 ChemAxon
pKa (strongest basic) -4.1 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 86.99 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 47.15 ChemAxon
Polarizability 18.45 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
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
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Epidermis
  • Thyroid Gland
  • Adrenal Gland
Pathways
Name SMPDB Link KEGG Link
Tyrosine Metabolism SMP00006 map00350 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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0.035 +/- 0.008 uM Adult (>18 years old) Male Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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3.67 +/- 2.12 umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and Quantified
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10.0 (0.3-20.0) umol/mmol creatinine Infant (0-1 year old) Not Specified Normal Not Available
Urine Detected and Quantified
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2.3 (1.0-3.4) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and Quantified
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1.2 +/- 0.5 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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12.5 (3.7-21.8) umol/mmol creatinine Newborn (0-30 days old) Both Normal Not Available
Urine Detected and Quantified
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12.4 (11.6-25.9) umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Urine Detected and Quantified
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6.5 (1.3-11.5) umol/mmol creatinine Children (1-13 year old) Both Normal Children aged 2-6 years
Urine Detected and Quantified
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6.5 (2.9-13.0) umol/mmol creatinine Children (1-13 year old) Both Normal Children aged 6-10 years
Urine Detected and Quantified
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5.2 (2.5-16.1) umol/mmol creatinine Children (1-13 year old) Both Normal Not Available
Urine Detected and Quantified
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<=3.289 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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1.6 (0.6-2.8) umol/mmol creatinine Adult (>18 years old) Both Normal by GC-MS
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
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0.15 (0.00-0.30) umol/mmol creatinine Infant (0-1 year old) Male Aromatic L-amino acid decarboxylase deficiency Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Hypertension (mild) After 4-wk comsumption of polyphenol-rich MIX....
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Hypertension (mild) After 4-wk comsumption of polyphenol-rich GJX...
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 FDB021931
    KNApSAcK ID Not Available
    Chemspider ID 643307 Link_out
    KEGG Compound ID C05584 Link_out
    BioCyc ID Not Available
    BiGG ID 46071 Link_out
    Wikipedia Link Vanillylmandelic acid Link_out
    NuGOwiki Link HMDB00291 Link_out
    Metagene Link HMDB00291 Link_out
    METLIN ID 697 Link_out
    PubChem Compound 736172 Link_out
    PDB ID Not Available
    ChEBI ID 1127735 Link_out
    References
    Synthesis Reference Recondo, E. F.; Rinderknecht, H. Preparation of epinephrine and norepinephrine metabolites, 3-methoxy-4-hydroxymandelic acid and 3,4-dihydroxymandelic acid. Journal of Organic Chemistry (1960), 25 2248-50.
    Material Safety Data Sheet (MSDS) Download (PDF)
    General References
    1. Frank K, Raue F, Gottswinter J, Heinrich U, Meybier H, Ziegler R: Importance of early diagnosis and follow-up in multiple endocrine neoplasia (MEN II B). Eur J Pediatr. 1984 Dec;143(2):112-6. Pubmed: 6394335 Link_out
    2. Takahashi S, Godse DD, Warsh JJ, Stancer HC: A gas chromatographic-mass spectrometric (GC-MS) assay for 3-methoxy-4-hydroxyphenethyleneglycol and vanilmandelic acid in human serum. Clin Chim Acta. 1977 Dec 1;81(2):182-92. Pubmed: 589798 Link_out
    3. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979 Link_out
    4. Suga K, Shimizu K, Nishigauchi K, Kume N, Kawamura T, Matsunaga N: [A case of bilateral adrenal neuroblastomas detected by bone scintigraphy] Kaku Igaku. 1996 Dec;33(12):1337-42. Pubmed: 9023440 Link_out
    5. Hartleb J, Eue S, Kemper A: Simultaneous analysis of homovanillic acid, 5-hydroxyindoleacetic acid, 3-methoxy-4-hydroxyphenylethylene glycol and vanilmandelic acid in plasma from alcoholics by high-performance liquid chromatography with electrochemical detection. Critical comparison of solid-phase and liquid-liquid extraction methods. J Chromatogr. 1993 Dec 22;622(2):161-71. Pubmed: 7512090 Link_out
    6. Dias PL, Amarasiri AA: 4-hydroxy-3-methoxymandelic acid (HMMA) excretion in retinoblastoma. Br J Ophthalmol. 1978 Aug;62(8):525-7. Pubmed: 687548 Link_out
    7. Saran RK, Sahuja RC, Gupta NN, Hasan M, Bhargava KP, Shanker K, Kishor K: 3-Methoxy-4-hydroxyphenylglycol in cerebrospinal fluid and vanillylmandelic acid in urine of humans with hypertension. Science. 1978 Apr 21;200(4339):317-8. Pubmed: 635588 Link_out
    8. Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. Pubmed: 12649306 Link_out
    9. Strittmatter M, Grauer M, Isenberg E, Hamann G, Fischer C, Hoffmann KH, Blaes F, Schimrigk K: Cerebrospinal fluid neuropeptides and monoaminergic transmitters in patients with trigeminal neuralgia. Headache. 1997 Apr;37(4):211-6. Pubmed: 9150615 Link_out
    10. Zambotti F, Blau K, King GS, Campbell S, Sandler M: Monoamine metabolites and related compounds in human amniotic fluid: assay by gas chromatography and gas chromatography-mass spectrometry. Clin Chim Acta. 1975 Jun 20;61(3):247-56. Pubmed: 1149252 Link_out
    11. Drebing CJ, Freedman R, Waldo M, Gerhardt GA: Unconjugated methoxylated catecholamine metabolites in human saliva. Quantitation methodology and comparison with plasma levels. Biomed Chromatogr. 1989 Sep;3(5):217-20. Pubmed: 2804429 Link_out
    12. Silbergeld EK, Chisolm JJ Jr: Lead poisoning: altered urinary catecholamine metabolites as indicators of intoxication in mice and children. Science. 1976 Apr 9;192(4235):153-5. Pubmed: 1257763 Link_out
    13. Bostrom B, Mirkin BL: Elevation of cerebrospinal fluid catecholamine metabolites in patients with intracranial tumors of neuroectodermal origin. J Clin Oncol. 1987 Jul;5(7):1090-7. Pubmed: 3598613 Link_out
    14. Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. Pubmed: 6085021 Link_out
    15. Afonso D, Castellanos MA, Rodriguez M: Determination of monoamines and indoles in amniotic fluid by high-performance liquid chromatography-electrochemical detection. J Chromatogr. 1990 Jun 8;528(1):101-9. Pubmed: 1696583 Link_out
    Enzymes
    Name: Catechol O-methyltransferase
    Reactions:
    • S-adenosyl-L-methionine + a catechol = S-adenosyl-L-homocysteine + a guaiacol [RN:R07330]
    Gene Name: COMT
    Uniprot ID: P21964 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Aldehyde dehydrogenase, dimeric NADP-preferring
    Reactions:
    • an aldehyde + NAD(P)+ + H2O = an acid + NAD(P)H + H+ [RN:R00538 R00634]
    Gene Name: ALDH3A1
    Uniprot ID: P30838 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Aldehyde dehydrogenase family 1 member A3
    Reactions:
    • an aldehyde + NAD(P)+ + H2O = an acid + NAD(P)H + H+ [RN:R00538 R00634]
    Gene Name: ALDH1A3
    Uniprot ID: P47895 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Aldehyde dehydrogenase family 3 member B2
    Reactions:
    • an aldehyde + NAD(P)+ + H2O = an acid + NAD(P)H + H+ [RN:R00538 R00634]
    Gene Name: ALDH3B2
    Uniprot ID: P48448 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Aldehyde dehydrogenase family 3 member B1
    Reactions:
    • an aldehyde + NAD(P)+ + H2O = an acid + NAD(P)H + H+ [RN:R00538 R00634]
    Gene Name: ALDH3B1
    Uniprot ID: P43353 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA