Showing metabocard for Mandelic acid (BMDB0000703)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:35:10 UTC
Update Date2020-04-22 15:04:53 UTC
BMDB IDBMDB0000703
Secondary Accession Numbers
  • BMDB00703
Metabolite Identification
Common NameMandelic acid
DescriptionMandelic acid, also known as L-mandelate or 2-phenylglycolate, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Mandelic acid exists in all living organisms, ranging from bacteria to humans. Mandelic acid, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis and colorectal cancer; mandelic acid has also been linked to the inborn metabolic disorder phenylketonuria. Based on a literature review a significant number of articles have been published on Mandelic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-2-Hydroxy-2-phenylacetic acidChEBI
(S)-alpha-Hydroxybenzeneacetic acidChEBI
(S)-MandelsaeureChEBI
L-Mandelic acidChEBI
(S)-2-Hydroxy-2-phenylacetateKegg
(S)-Mandelic acidKegg
(S)-a-HydroxybenzeneacetateGenerator
(S)-a-Hydroxybenzeneacetic acidGenerator
(S)-alpha-HydroxybenzeneacetateGenerator
(S)-Α-hydroxybenzeneacetateGenerator
(S)-Α-hydroxybenzeneacetic acidGenerator
L-MandelateGenerator
(S)-MandelateGenerator
MandelateGenerator
(RS)-MandelateHMDB
(RS)-Mandelic acidHMDB
2-Hydroxy-2-phenylacetateHMDB
2-Hydroxy-2-phenylacetic acidHMDB
2-Hydroxy-2-phenylethanoateHMDB
2-Hydroxy-2-phenylethanoic acidHMDB
2-Phenyl-2-hydroxyacetateHMDB
2-Phenyl-2-hydroxyacetic acidHMDB
2-PhenylglycolateHMDB
2-Phenylglycolic acidHMDB
a-Hydroxy-a-toluateHMDB
a-Hydroxy-a-toluic acidHMDB
a-HydroxybenzeneacetateHMDB
a-Hydroxybenzeneacetic acidHMDB
a-HydroxyphenylacetateHMDB
a-Hydroxyphenylacetic acidHMDB
Almond acidHMDB
alpha-Hydroxy-alpha-toluateHMDB
alpha-Hydroxy-alpha-toluic acidHMDB
alpha-HydroxybenzeneacetateHMDB
alpha-Hydroxybenzeneacetic acidHMDB
alpha-HydroxyphenylacetateHMDB
alpha-Hydroxyphenylacetic acidHMDB
AmygdalateHMDB
Amygdalic acidHMDB
DL-AmygdalateHMDB
DL-Amygdalic acidHMDB
DL-Hydroxy(phenyl)acetateHMDB
DL-Hydroxy(phenyl)acetic acidHMDB
DL-MandelateHMDB
DL-Mandelic acidHMDB
ParamandelateHMDB
Paramandelic acidHMDB
PhenylglycolateHMDB
Phenylglycolic acidHMDB
PhenylhydroxyacetateHMDB
Phenylhydroxyacetic acidHMDB
UromalineHMDB
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name(2S)-2-hydroxy-2-phenylacetic acid
Traditional Name(S)-mandelic acid
CAS Registry Number90-64-2
SMILES
O[C@H](C(O)=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1
InChI KeyIWYDHOAUDWTVEP-ZETCQYMHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point120 - 122 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility181.0 mg/mLNot Available
LogP0.62HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP0.66ALOGPS
logP0.9ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.7 m³·mol⁻¹ChemAxon
Polarizability14.66 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004j-0900000000-b53183d87b331db9b7dbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004j-0900000000-b53183d87b331db9b7dbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9700000000-2d141c7d9cfc97cc9b76View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2910000000-de71bbd7bcfd35e2bbe5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-0900000000-31443907299c1634fe9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0pdi-4900000000-d32dc8f06b5e94c7b3b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfr-1900000000-f1e179f7f6654c244250View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-15fb1f5429449730eb57View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-1900000000-66724d8d0612c1da0f0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4l-9500000000-6d480b6841c2a90ea872View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4l-9100000000-817dbc1408c9336f23ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-f924dd96a6635e2ad5b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-15fb1f5429449730eb57View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-1900000000-66724d8d0612c1da0f0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9500000000-96b7d7c57c085b66c0aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9100000000-817dbc1408c9336f23ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-f924dd96a6635e2ad5b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0udi-0900000000-2d7a2f949d0d3d446a49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-0900000000-c0c136dca9a3ed6fd376View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-b1718872e9065a923bc9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0900000000-036a833e3ff39dd5fa3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-d3c9a003466ac58be74fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pdi-5900000000-cadf8b3761e31a6e33c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-b906b74a2aa4ffe7faccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-1900000000-62ebdc9508b56ca81f8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-7900000000-1f515b6e62c594acde14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9000000000-08231d859a98c3eafb22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zg0-0900000000-dc883eccc7ede3626274View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-43028c230f4ad5a4568cView in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000703
DrugBank IDDB03357
Phenol Explorer Compound IDNot Available
FooDB IDFDB022191
KNApSAcK IDC00037426
Chemspider ID388690
KEGG Compound IDC01984
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMandelic acid
METLIN ID5671
PubChem Compound439616
PDB IDNot Available
ChEBI ID32800
References
Synthesis ReferenceChen, Jianfeng; Chen, Hao. Process for preparation of mandelic acid by membrane separation technology. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 7pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available