You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-09-22 21:06:29 UTC
HMDB IDHMDB00750
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Hydroxymandelic acid
Descriptionm-hydroxymandelic acid or 3-hyrodxymandelic acid is a metabolic breakdown product of m-octopamine, m-synephrine (phenylephrine) and m-tyrosine. It is a naturally occuring catecholamine metabolite. Concentrations of m-hydroxymandelic acid can be elevated 20- to 30-fold in neuroblastoma patients.
Structure
Thumb
Synonyms
ValueSource
3-HydroxymandelateHMDB
3-Hydroxyphenylglycolic acidHMDB
alpha,3-Dihydroxybenzeneacetic acidHMDB
DL-3-HydroxymandelateHMDB
DL-3-Hydroxymandelic acidHMDB
DL-Hydroxy(m-hydroxyphenyl)acetic acidHMDB
Hydroxy(3-hydroxyphenyl)acetic acidHMDB
m-Hydroxy-(6ci,7ci,8ci)mandelateHMDB
m-Hydroxy-(6ci,7ci,8ci)mandelic acidHMDB
m-HydroxymandelateHMDB
m-Hydroxymandelic acidHMDB
Meta-hydroxymandelic acidHMDB
MHMAHMDB
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name2-hydroxy-2-(3-hydroxyphenyl)acetic acid
Traditional NameMHMA
CAS Registry Number17119-15-2
SMILES
OC(C(O)=O)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C8H8O4/c9-6-3-1-2-5(4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)
InChI KeyInChIKey=OLSDAJRAVOVKLG-UHFFFAOYSA-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
  • Phenol
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility31 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.5 mg/mLALOGPS
logP0.89ALOGPS
logP0.59ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.68 m3·mol-1ChemAxon
Polarizability15.55 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)splash10-00di-0900000000-10beec4c3472d3afb28cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-0900000000-5a6c0f2c681a7da489f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00dl-9800000000-49e33a7a57260ed160a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00di-0900000000-72199f89fe731fcb25d0View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Kidney
  • Liver
  • Urine
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified10.527 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified10.527 +/- 0.0595 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedBoth
Normal
details
UrineDetected and Quantified0.023 +/- 0.014 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified700.0 (670.0 - 1030.0) uMAdult (>18 years old)Both
Kidney disease
    • Nieren- und Hochd...
details
Associated Disorders and Diseases
Disease References
Kidney disease
  1. Nieren- und Hochdruckkrankheiten (1978), 7(2), 62-74 (translated from German Kidney and Hypertension).
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022222
KNApSAcK IDNot Available
Chemspider ID78444
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00750
Metagene LinkHMDB00750
METLIN ID732
PubChem Compound86957
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceFanali S; Aturki Z Further study on the use of uncharged beta-cyclodextrin polymer in capillary electrophoresis: enantiomeric separation of some alpha-hydroxy acids. Electrophoresis (1995), 16(8), 1505-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Midgley JM, Couch MW, Crowley JR, Williams CM: Identification and quantitative determination of o- and m-hydroxymandelic acid in human urine. Biomed Mass Spectrom. 1979 Nov;6(11):485-90. [534686 ]
  2. Ibrahim KE, Midgley JM, Crowley JR, Williams CM: The mammalian metabolism of R-(-)-m-synephrine. J Pharm Pharmacol. 1983 Mar;35(3):144-7. [6132969 ]
  3. Gumbhir K, Mason WD: Determination of m-hydroxymandelic acid, m-hydroxyphenylglycol and their conjugates in human plasma using liquid chromatography with electrochemical detection. J Pharm Biomed Anal. 1994 Jul;12(7):943-9. [7981325 ]
  4. Crowley JR, Couch MW, Williams CM, Threatte RM, Fregly MJ: Normal excretion of m-hydroxymandelic acid in hypertensive patients. Clin Chim Acta. 1981 Jan 22;109(2):125-31. [7471493 ]