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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:30 UTC
HMDB IDHMDB00291
Secondary Accession NumbersNone
Metabolite Identification
Common NameVanillylmandelic acid
DescriptionVanillylmandelic 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
Synonyms
ValueSource
(4-Hydroxy-3-methoxyphenyl)glycolateHMDB
(4-Hydroxy-3-methoxyphenyl)glycolic acidHMDB
3-Methoxy-4-hydroxy-mandelic acidHMDB
3-Methoxy-4-hydroxymandelateHMDB
3-Methoxy-4-hydroxymandelic acidHMDB
3-Methoxy-4-hydroxyphenylhydroxyacetateHMDB
3-Methoxy-4-hydroxyphenylhydroxyacetic acidHMDB
4'-Hydroxy-3'-methoxymandelateHMDB
4'-Hydroxy-3'-methoxymandelic acidHMDB
4-Hydroxy 3-methoxymandelic acidHMDB
4-Hydroxy-3-methoxy-DL-mandelateHMDB
4-Hydroxy-3-methoxy-DL-mandelic acidHMDB
4-Hydroxy-3-methoxy-mandelateHMDB
4-Hydroxy-3-methoxy-mandelic acidHMDB
4-Hydroxy-3-methoxymandelateHMDB
4-Hydroxy-3-methoxymandelic acidHMDB
DL-3-Methoxy-4-hydroxymandelateHMDB
DL-3-Methoxy-4-hydroxymandelic acidHMDB
DL-4-Hydroxy-3-methoxymandelateHMDB
DL-4-Hydroxy-3-methoxymandelic acidHMDB
DL-VanillomandelateHMDB
DL-Vanillomandelic acidHMDB
DL-VanillylmandelateHMDB
DL-Vanillylmandelic acidHMDB
HMMAHMDB
Hydroxymethoxymandelic acidHMDB
Lopac-H-0131HMDB
Vainillylmandelic acidHMDB
VanillinmandelateHMDB
Vanillinmandelic acidHMDB
VanillomandelateHMDB
Vanillomandelic acidHMDB
Vanillyl-mandelic acidHMDB
VanillylmandelateHMDB
Vanillylmandellic acidHMDB
Vanillymandelic acidHMDB
VanilmandelateHMDB
Vanilmandelic acidHMDB
Vanilylmandelic acidHMDB
Vanyl-mandelic acidHMDB
Vanylmandelic acidHMDB
VMAHMDB
Chemical FormulaC9H10O5
Average Molecular Weight198.1727
Monoisotopic Molecular Weight198.05282343
IUPAC Name(2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
Traditional Name(S)-hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid
CAS Registry Number55-10-7
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 KeyInChIKey=CGQCWMIAEPEHNQ-QMMMGPOBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Methoxyphenol
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Phenol
  • Alkyl aryl ether
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point132 - 134 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.16 mg/mLALOGPS
logP0.94ALOGPS
logP0.43ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.11ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.15 m3·mol-1ChemAxon
Polarizability18.45 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000b-0900000000-1e2dedd8e81249787b29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000i-0900000000-3d2cd918dc6b76dfba3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000i-2900000000-b543807e43e5091abb53View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue Location
  • Adrenal Gland
  • Epidermis
  • Thyroid Gland
Pathways
NameSMPDB LinkKEGG Link
AlkaptonuriaSMP00169Not Available
Disulfiram PathwaySMP00429Not Available
Dopamine beta-hydroxylase deficiencySMP00498Not Available
HawkinsinuriaSMP00190Not Available
Monoamine oxidase-a deficiency (MAO-A)SMP00533Not Available
Tyrosine MetabolismSMP00006map00350
Tyrosinemia Type ISMP00218Not Available
Tyrosinemia, transient, of the newbornSMP00494Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.035 +/- 0.008 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.585 +/- 1.095 umol/mmol creatinineAdult (>18 years old)BothNot Available details
UrineDetected and Quantified3.67 +/- 2.12 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified7.758 +/- 2.944 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified10.0 (0.3-20.0) umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified5.93 +/- 3.016 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified2.3 (1.0-3.4) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.2 +/- 0.5 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified12.5 (3.7-21.8) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified12.4 (11.6-25.9) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified6.5 (1.3-11.5) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified6.5 (2.9-13.0) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified5.2 (2.5-16.1) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified<=3.289 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.6 (0.6-2.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified7.586 +/- 3.852 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified7.332 +/- 3.711 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.15 (0.00-0.30) umol/mmol creatinineInfant (0-1 year old)MaleAromatic L-amino acid decarboxylase deficiency details
UrineDetected and Quantified6.869 +/- 2.756 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Hypertension (mild)
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. [16288991 ]
Associated OMIM IDs
  • 107930 (Aromatic L-amino acid decarboxylase deficiency)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021931
KNApSAcK IDNot Available
Chemspider ID643307
KEGG Compound IDC05584
BioCyc IDNot Available
BiGG ID46071
Wikipedia LinkVanillylmandelic acid
NuGOwiki LinkHMDB00291
Metagene LinkHMDB00291
METLIN ID697
PubChem Compound736172
PDB IDNot Available
ChEBI ID1127735
References
Synthesis ReferenceRecondo, 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. 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. [8087979 ]
  2. Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [6085021 ]
  3. 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. [12649306 ]
  4. 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. [1257763 ]
  5. 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. [6394335 ]
  6. 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. [589798 ]
  7. 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. [9023440 ]
  8. 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. [7512090 ]
  9. Dias PL, Amarasiri AA: 4-hydroxy-3-methoxymandelic acid (HMMA) excretion in retinoblastoma. Br J Ophthalmol. 1978 Aug;62(8):525-7. [687548 ]
  10. 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. [635588 ]
  11. 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. [9150615 ]
  12. 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. [1149252 ]
  13. 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. [2804429 ]
  14. 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. [3598613 ]
  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. [1696583 ]

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
S-Adenosylmethionine + 3,4-Dihydroxymandelic acid → S-Adenosylhomocysteine + Vanillylmandelic aciddetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water → Vanillylmandelic acid + NADH + Hydrogen Iondetails
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water → Vanillylmandelic acid + NADH + Hydrogen Iondetails
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water → Vanillylmandelic acid + NADH + Hydrogen Iondetails
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245
Reactions
3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water → Vanillylmandelic acid + NADH + Hydrogen Iondetails
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPH + Hydrogen Iondetails