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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 04:56:21 UTC
Update Date2021-09-14 15:02:28 UTC
HMDB IDHMDB0062635
Secondary Accession Numbers
  • HMDB62635
Metabolite Identification
Common Name(R)-mandelic Acid
Description(R)-mandelic Acid, also known as (R)-mandelsaeure or D-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 (R)-mandelic Acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (R)-mandelic Acid exists in all living organisms, ranging from bacteria to humans. The (R)-enantiomer of mandelic acid.
Structure
Data?1563866340
Synonyms
ValueSource
(-)-(R)-Mandelic acidChEBI
(-)-alpha-Hydroxyphenylacetic acidChEBI
(-)-Mandelic acidChEBI
(2R)-2-Hydroxy-2-phenylacetic acidChEBI
(R)-2-Hydroxy-2-phenylacetic acidChEBI
(R)-alpha-Hydroxybenzeneacetic acidChEBI
(R)-alpha-Hydroxyphenylacetic acidChEBI
(R)-MandelsaeureChEBI
D(-)-Mandelic acidChEBI
D-2-Phenylglycolic acidChEBI
D-Mandelic acidChEBI
(R)-2-Hydroxy-2-phenylacetateKegg
(-)-(R)-MandelateGenerator
(-)-a-HydroxyphenylacetateGenerator
(-)-a-Hydroxyphenylacetic acidGenerator
(-)-alpha-HydroxyphenylacetateGenerator
(-)-Α-hydroxyphenylacetateGenerator
(-)-Α-hydroxyphenylacetic acidGenerator
(-)-MandelateGenerator
(2R)-2-Hydroxy-2-phenylacetateGenerator
(R)-a-HydroxybenzeneacetateGenerator
(R)-a-Hydroxybenzeneacetic acidGenerator
(R)-alpha-HydroxybenzeneacetateGenerator
(R)-Α-hydroxybenzeneacetateGenerator
(R)-Α-hydroxybenzeneacetic acidGenerator
(R)-a-HydroxyphenylacetateGenerator
(R)-a-Hydroxyphenylacetic acidGenerator
(R)-alpha-HydroxyphenylacetateGenerator
(R)-Α-hydroxyphenylacetateGenerator
(R)-Α-hydroxyphenylacetic acidGenerator
D(-)-MandelateGenerator
D-2-PhenylglycolateGenerator
D-MandelateGenerator
(R)-MandelateGenerator
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name(2R)-2-hydroxy-2-phenylacetic acid
Traditional Namemandelic acid, (+-)-
CAS Registry Number611-71-2
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-/m1/s1
InChI KeyIWYDHOAUDWTVEP-SSDOTTSWSA-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
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility16.8 g/lALOGPS
LogP0.66ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(0.66) g/LALOGPS
logP10(0.9) g/LChemAxon
logS10(-0.96) g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.85331661259
DarkChem[M-H]-130.38531661259
DeepCCS[M+H]+132.78630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-mandelic AcidO[C@@H](C(O)=O)C1=CC=CC=C12756.2Standard polar33892256
(R)-mandelic AcidO[C@@H](C(O)=O)C1=CC=CC=C11413.7Standard non polar33892256
(R)-mandelic AcidO[C@@H](C(O)=O)C1=CC=CC=C11449.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-mandelic Acid,1TMS,isomer #1C[Si](C)(C)O[C@@H](C(=O)O)C1=CC=CC=C11460.9Semi standard non polar33892256
(R)-mandelic Acid,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](O)C1=CC=CC=C11414.7Semi standard non polar33892256
(R)-mandelic Acid,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)C1=CC=CC=C11474.7Semi standard non polar33892256
(R)-mandelic Acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H](C(=O)O)C1=CC=CC=C11697.0Semi standard non polar33892256
(R)-mandelic Acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)C1=CC=CC=C11652.5Semi standard non polar33892256
(R)-mandelic Acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C11927.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (R)-mandelic Acid EI-B (Non-derivatized)splash10-004i-0900000000-da7c8450b1708d6b5b442017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (R)-mandelic Acid GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-bf406a068b57bcc07ca22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (R)-mandelic Acid EI-B (Non-derivatized)splash10-004i-0900000000-da7c8450b1708d6b5b442018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (R)-mandelic Acid GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-bf406a068b57bcc07ca22018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-mandelic Acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9600000000-0d67f110027658a584a42017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-mandelic Acid GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2910000000-de71bbd7bcfd35e2bbe52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-mandelic Acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-mandelic Acid LC-ESI-QQ , negative-QTOFsplash10-0zfr-5900000000-45499f2c996208e0143f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-mandelic Acid LC-ESI-QQ , negative-QTOFsplash10-0a4i-9100000000-b577195913c64f43bc8f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-mandelic Acid LC-ESI-QQ , negative-QTOFsplash10-0a4i-9000000000-3030385b2c46c76f7d402017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-mandelic Acid LC-ESI-QQ , negative-QTOFsplash10-0a4i-9000000000-d57db09a0e7c73a976bc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-mandelic Acid LC-ESI-QQ , negative-QTOFsplash10-0a4i-9000000000-5a80a2a733ffb7d2962f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-mandelic Acid LC-ESI-QTOF , negative-QTOFsplash10-0udi-0900000000-26a5fcf7f098faa99c2d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-mandelic Acid 10V, Positive-QTOFsplash10-0zg0-0900000000-dc883eccc7ede36262742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-mandelic Acid 20V, Positive-QTOFsplash10-0a4i-1900000000-43028c230f4ad5a4568c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-mandelic Acid 40V, Positive-QTOFsplash10-0pdi-9500000000-d3b486d397a2e852f3a42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-mandelic Acid 10V, Negative-QTOFsplash10-0zfr-0900000000-d3c9a003466ac58be74f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-mandelic Acid 20V, Negative-QTOFsplash10-0pdi-5900000000-cadf8b3761e31a6e33c52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-mandelic Acid 40V, Negative-QTOFsplash10-004i-9200000000-b906b74a2aa4ffe7facc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-mandelic Acid 10V, Positive-QTOFsplash10-00kr-1900000000-1f844c7b2df8e11ad51c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-mandelic Acid 20V, Positive-QTOFsplash10-004i-9100000000-8dc4c2ee7a401fec29d62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-mandelic Acid 40V, Positive-QTOFsplash10-004i-9000000000-a072eb0e14ea716c51b02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-mandelic Acid 10V, Negative-QTOFsplash10-0zfr-1900000000-62ebdc9508b56ca81f8a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-mandelic Acid 20V, Negative-QTOFsplash10-0a6r-7900000000-1f515b6e62c594acde142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-mandelic Acid 40V, Negative-QTOFsplash10-01t9-9000000000-08231d859a98c3eafb222021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02280
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01983
BioCyc IDCPD-121
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11914
PDB IDNot Available
ChEBI ID17656
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available