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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:41 UTC
HMDB IDHMDB0000291
Secondary Accession Numbers
  • HMDB00291
  • HMDB0133489
Metabolite Identification
Common NameVanillylmandelic acid
DescriptionVanillylmandelic acid, also known as vanillylmandelate or VMA, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Vanillylmandelic acid is a sweet and vanilla tasting compound. Vanillylmandelic acid (VMA) is a chemical intermediate in the synthesis of artificial vanilla flavorings and is an end-stage metabolite of the catecholamines (dopamine, epinephrine, and norepinephrine). Vanillylmandelic acid exists in all living organisms, ranging from bacteria to plants to humans. Within humans, vanillylmandelic acid participates in a number of enzymatic reactions. In particular, vanillylmandelic acid can be biosynthesized from 3-methoxy-4-hydroxyphenylglycolaldehyde through its interaction with the enzyme aldehyde dehydrogenase. In addition, vanillylmandelic acid and pyrocatechol can be biosynthesized from 3,4-dihydroxymandelic acid and guaiacol through the action of the enzyme catechol O-methyltransferase. Urinary VMA is elevated in patients with tumors that secrete catecholamines. Urinary VMA tests may also be used to diagnose neuroblastomas, and to monitor treatment of these conditions. VMA urinalysis tests can be used to diagnose an adrenal gland tumor called pheochromocytoma, a tumor of catecholamine-secreting chromaffin cells. Vanillylmandelic acid (VMA) is produced in the liver and is a major product of norepinephrine and epinephrine metabolism excreted in the urine.
Structure
Data?1676999681
Synonyms
ValueSource
VanillylmandelateGenerator
(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
Vanillylmandellic acidHMDB
Vanillymandelic acidHMDB
VanilmandelateHMDB
Vanilmandelic acidHMDB
Vanilylmandelic acidHMDB
Vanyl-mandelic acidHMDB
Vanylmandelic acidHMDB
VMAHMDB
2-Phenyllactic acidHMDB
VMA CPDHMDB
Atrolactic acidHMDB
Atrolactic acid monosodium salt, (S)-isomerHMDB
Atrolactic acid, (+-)-isomerHMDB
Hydroxymethylmandelic acidHMDB
(+)-4-Hydroxy-3-methoxymandelic acidHMDB
(+)-Vanilmandelic acidHMDB
(2S)-2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acidHMDB
(S)-4-Hydroxy-3-methoxymandelic acidHMDB
(alphaS)-alpha,4-Dihydroxy-3-methoxybenzeneacetic acidHMDB
(αS)-α,4-Dihydroxy-3-methoxybenzeneacetic acidHMDB
2-(4'-Hydroxy-3'-methoxyphenyl)-2-hydroxyethanoic acidHMDB
2-(4’-Hydroxy-3’-methoxyphenyl)-2-hydroxyethanoic acidHMDB
2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acidHMDB
4’-Hydroxy-3’-methoxymandelic acidHMDB
L-(+)-3-Methoxy-4-hydroxymandelic acidHMDB
Vanillylmandelic acidHMDB
alpha,4-Dihydroxy-3-methoxybenzeneacetic acidHMDB
α,4-Dihydroxy-3-methoxybenzeneacetic acidHMDB
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 Number13244-77-4
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 KeyCGQCWMIAEPEHNQ-QMMMGPOBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point132 - 134 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available140.904http://allccs.zhulab.cn/database/detail?ID=AllCCS00000288
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.16 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.15 m³·mol⁻¹ChemAxon
Polarizability18.45 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.28931661259
DarkChem[M-H]-146.47631661259
AllCCS[M+H]+143.79832859911
AllCCS[M-H]-139.89632859911
DeepCCS[M+H]+144.71530932474
DeepCCS[M-H]-142.3430932474
DeepCCS[M-2H]-175.89930932474
DeepCCS[M+Na]+150.79130932474
AllCCS[M+H]+143.832859911
AllCCS[M+H-H2O]+139.732859911
AllCCS[M+NH4]+147.632859911
AllCCS[M+Na]+148.732859911
AllCCS[M-H]-139.932859911
AllCCS[M+Na-2H]-140.632859911
AllCCS[M+HCOO]-141.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Vanillylmandelic acidCOC1=C(O)C=CC(=C1)[C@H](O)C(O)=O3318.2Standard polar33892256
Vanillylmandelic acidCOC1=C(O)C=CC(=C1)[C@H](O)C(O)=O1822.7Standard non polar33892256
Vanillylmandelic acidCOC1=C(O)C=CC(=C1)[C@H](O)C(O)=O1769.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Vanillylmandelic acid,1TMS,isomer #1COC1=CC([C@H](O)C(=O)O)=CC=C1O[Si](C)(C)C1885.0Semi standard non polar33892256
Vanillylmandelic acid,1TMS,isomer #2COC1=CC([C@H](O[Si](C)(C)C)C(=O)O)=CC=C1O1852.5Semi standard non polar33892256
Vanillylmandelic acid,1TMS,isomer #3COC1=CC([C@H](O)C(=O)O[Si](C)(C)C)=CC=C1O1814.7Semi standard non polar33892256
Vanillylmandelic acid,2TMS,isomer #1COC1=CC([C@H](O[Si](C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C1884.8Semi standard non polar33892256
Vanillylmandelic acid,2TMS,isomer #2COC1=CC([C@H](O)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1880.9Semi standard non polar33892256
Vanillylmandelic acid,2TMS,isomer #3COC1=CC([C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O1897.2Semi standard non polar33892256
Vanillylmandelic acid,3TMS,isomer #1COC1=CC([C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1912.8Semi standard non polar33892256
Vanillylmandelic acid,1TBDMS,isomer #1COC1=CC([C@H](O)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C2170.0Semi standard non polar33892256
Vanillylmandelic acid,1TBDMS,isomer #2COC1=CC([C@H](O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O2138.0Semi standard non polar33892256
Vanillylmandelic acid,1TBDMS,isomer #3COC1=CC([C@H](O)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O2073.1Semi standard non polar33892256
Vanillylmandelic acid,2TBDMS,isomer #1COC1=CC([C@H](O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C2416.3Semi standard non polar33892256
Vanillylmandelic acid,2TBDMS,isomer #2COC1=CC([C@H](O)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2359.0Semi standard non polar33892256
Vanillylmandelic acid,2TBDMS,isomer #3COC1=CC([C@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O2371.1Semi standard non polar33892256
Vanillylmandelic acid,3TBDMS,isomer #1COC1=CC([C@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2582.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3900000000-97b85fd5a9736a5d5eb02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (3 TMS) - 70eV, Positivesplash10-009t-7396100000-b5450c24921a68f5f6b32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillylmandelic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-000b-0900000000-1e2dedd8e81249787b292012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillylmandelic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-000i-0900000000-3d2cd918dc6b76dfba3f2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillylmandelic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-000i-2900000000-b543807e43e5091abb532012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillylmandelic acid 40V, Negative-QTOFsplash10-000i-1900000000-1c88ce4d32680e3379de2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillylmandelic acid 10V, Negative-QTOFsplash10-000i-0900000000-30e1c8cb4fa5443c687e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillylmandelic acid 20V, Negative-QTOFsplash10-000i-0900000000-c4c762f850d22fee62812021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillylmandelic acid 10V, Negative-QTOFsplash10-0f6t-0900000000-1308d37a2313f54793652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillylmandelic acid 20V, Negative-QTOFsplash10-0fmj-0900000000-bcdff30bcec2389ffef62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillylmandelic acid 40V, Negative-QTOFsplash10-0ab9-3900000000-cd2db271b5a0926adfeb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillylmandelic acid 10V, Negative-QTOFsplash10-00dj-9700000000-2c212037a037fcd229d02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillylmandelic acid 20V, Negative-QTOFsplash10-0kg9-1900000000-81b2ab77bf3382c9f5de2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillylmandelic acid 40V, Negative-QTOFsplash10-0002-4900000000-e3b77a4d29235649ecce2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillylmandelic acid 10V, Positive-QTOFsplash10-0f8a-0900000000-04d80bfab4984d07e4792017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillylmandelic acid 20V, Positive-QTOFsplash10-0udi-0900000000-23d4830296b7ea07f0d52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillylmandelic acid 40V, Positive-QTOFsplash10-0fki-5900000000-9b9364530caece4b6c122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillylmandelic acid 10V, Positive-QTOFsplash10-0f7t-0900000000-ac32d971a0581e8b6cb62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillylmandelic acid 20V, Positive-QTOFsplash10-000i-0900000000-bce2f2854f319781df102021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillylmandelic acid 40V, Positive-QTOFsplash10-0umi-9700000000-311af8dc825e2dd026142021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Adrenal Gland
  • Epidermis
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.035 +/- 0.008 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified4.906 +/- 1.769 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified5.0776 +/- 1.712 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified5.135 +/- 1.826 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified6.2 umol/mmol creatinineInfant (0-1 year old)Both
Normal
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
    • Analysis of 30 no...
details
UrineDetected and Quantified13.24 +/- 5.3 umol/mmol creatinineInfant (6 months - <1 year old)Both
Normal
details
UrineDetected and Quantified5.38 +/- 1.83 umol/mmol creatinineInfant (6 months - <1 year old)Both
Normal
details
UrineDetected and Quantified4.18 +/- 1.55 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified6.19 +/- 2.014 umol/mmol creatinineInfant (1 - 6 months old)Both
Normal
details
UrineDetected and Quantified6.22 +/- 2.32 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified10.0 (0.3-20.0) umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified3.22-9.08 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified5.68 +/- 2.19 umol/mmol creatinineInfant (6 months - <1 year old)Both
Normal
details
UrineDetected and Quantified5.93 +/- 3.016 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified1.6-2.2 umol/mmol creatinineAdult (>18 years old)FemaleNormal 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 Quantified0.300-19.700 umol/mmol creatinineChildren (1-13 years old)Female
Normal
details
UrineDetected and Quantified1.1-1.7 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.5-7.6 umol/mmol creatinineAdult (>18 years old)MaleNormal 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
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified9.128 +/- 4.450 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria
details
UrineDetected and Quantified7.586 +/- 3.852 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified7.332 +/- 3.711 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
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
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
UrineDetected and Quantified0.2-0.4 umol/mmol creatinineAdult (>18 years old)MaleBrunner Syndrome details
UrineDetected and Quantified0.5 umol/mmol creatinineChildren (1-13 years old)Female
Aromatic L-amino acid decarboxylase deficiency
details
UrineDetected and Quantified0.9 umol/mmol creatinineInfant (0-1 year old)Female
Aromatic L-amino acid decarboxylase deficiency
details
UrineDetected and Quantified15.404 +/- 14.833 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria
details
UrineDetected and Quantified4.564 +/- 1.369 umol/mmol creatinineChildren (1-13 years old)BothPhenylketonuria details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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 ]
  2. Abeling NG, van Gennip AH, Barth PG, van Cruchten A, Westra M, Wijburg FA: Aromatic L-amino acid decarboxylase deficiency: a new case with a mild clinical presentation and unexpected laboratory findings. J Inherit Metab Dis. 1998 Jun;21(3):240-2. [PubMed:9686366 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Phenylketonuria
  1. Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567 ]
Brunner Syndrome
  1. Brunner HG, Nelen MR, van Zandvoort P, Abeling NG, van Gennip AH, Wolters EC, Kuiper MA, Ropers HH, van Oost BA: X-linked borderline mental retardation with prominent behavioral disturbance: phenotype, genetic localization, and evidence for disturbed monoamine metabolism. Am J Hum Genet. 1993 Jun;52(6):1032-9. [PubMed:8503438 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021931
KNApSAcK IDNot Available
Chemspider ID643307
KEGG Compound IDC05584
BioCyc IDNot Available
BiGG ID46071
Wikipedia LinkVanillylmandelic acid
METLIN ID697
PubChem Compound736172
PDB IDNot Available
ChEBI ID1127735
Food Biomarker OntologyNot Available
VMH ID3MOX4HOXM
MarkerDB IDMDB00000136
Good Scents IDNot Available
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. [PubMed:8087979 ]
  2. Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:7512090 ]
  9. Dias PL, Amarasiri AA: 4-hydroxy-3-methoxymandelic acid (HMMA) excretion in retinoblastoma. Br J Ophthalmol. 1978 Aug;62(8):525-7. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:1696583 ]
  16. Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]

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