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Showing metabocard for 3-Hydroxymandelic acid (HMDB00750)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:14 -0700
HMDB ID HMDB00750
Secondary Accession Numbers None
Metabolite Identification
Common Name 3-Hydroxymandelic acid
Description m-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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3-Hydroxymandelate
  2. 3-Hydroxyphenylglycolic acid
  3. alpha,3-Dihydroxybenzeneacetic acid
  4. DL-3-Hydroxymandelate
  5. DL-3-Hydroxymandelic acid
  6. DL-hydroxy(m-hydroxyphenyl)acetic acid
  7. Hydroxy(3-hydroxyphenyl)acetic acid
  8. m-Hydroxy-(6CI,7CI,8CI)Mandelate
  9. m-Hydroxy-(6CI,7CI,8CI)Mandelic acid
  10. M-Hydroxymandelate
  11. M-Hydroxymandelic acid
  12. Meta-hydroxymandelic acid
  13. MHMA
Chemical Formula C8H8O4
Average Molecular Weight 168.1467
Monoisotopic Molecular Weight 168.042258744
IUPAC Name 2-hydroxy-2-(3-hydroxyphenyl)acetic acid
Traditional IUPAC Name hydroxy(3-hydroxyphenyl)acetic acid
CAS Registry Number 17119-15-2
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 Key OLSDAJRAVOVKLG-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenylacetic Acid Derivatives
Sub Class N/A
Other Descriptors
  • Organic Compounds
Substituents
  • Alpha Hydroxy Acid
  • Benzyl Alcohol Derivative
  • Carboxylic Acid
  • Phenol
  • Phenol Derivative
  • Secondary Alcohol
Direct Parent Phenylacetic Acid 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 Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility 31 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 10.5 g/L ALOGPS
LogP 0.89 ALOGPS
LogP 0.59 ChemAxon
LogS -1.20 ALOGPS
pKa (strongest acidic) 3.3 ChemAxon
pKa (strongest basic) -4.1 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 77.76 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 40.68 ChemAxon
Polarizability 15.55 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
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
  • Urine
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
0.023 +/- 0.014 umol/mmol creatinine Adult (>18 years old) Not Specified Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
700.0 (670.0 - 1030.0) uM Adult (>18 years old) Both Kidney disease Terminal renal insufficiency during...
Associated Disorders and Diseases
Disease References
Kidney disease
    • Nieren- und Hochdruckkrankheiten (1978), 7(2), 62-74 (translated from German Kidney and Hypertension).
    Associated OMIM IDs None
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB022222
    KNApSAcK ID Not Available
    Chemspider ID 78444 Link_out
    KEGG Compound ID Not Available
    BioCyc ID Not Available
    BiGG ID Not Available
    Wikipedia Link Not Available
    NuGOwiki Link HMDB00750 Link_out
    Metagene Link HMDB00750 Link_out
    METLIN ID 732 Link_out
    PubChem Compound 86957 Link_out
    PDB ID Not Available
    ChEBI ID Not Available
    References
    Synthesis Reference Fanali 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. Pubmed: 534686 Link_out
    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. Pubmed: 6132969 Link_out
    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. Pubmed: 7981325 Link_out
    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. Pubmed: 7471493 Link_out