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Showing metabocard for (±)-2-Hydroxy-2-phenylacetonitrile (HMDB0034666)

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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:33:51 UTC
Update Date2019-07-23 06:16:40 UTC
HMDB IDHMDB0034666
Secondary Accession Numbers
  • HMDB34666
Metabolite Identification
Common Name(±)-2-Hydroxy-2-phenylacetonitrile
Description(±)-2-Hydroxy-2-phenylacetonitrile, also known as alpha-hydroxybenzeneacetonitrile or benzaldehyde cyanohydrin, 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. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase (±)-2-Hydroxy-2-phenylacetonitrile is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (±)-2-Hydroxy-2-phenylacetonitrile has been detected, but not quantified in, fruits. This could make (±)-2-hydroxy-2-phenylacetonitrile a potential biomarker for the consumption of these foods. Mandelonitrile is a chemical compound of the cyanohydrin class (±)-2-Hydroxy-2-phenylacetonitrile is a potentially toxic compound. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Oxygen therapy can also be administered.
Structure
Data?1563862600
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
alpha-HydroxybenzeneacetonitrileChEBI
Benzaldehyde cyanohydrinChEBI
Mandelic acid nitrileChEBI
PhenylglycolonitrileChEBI
a-HydroxybenzeneacetonitrileGenerator
Α-hydroxybenzeneacetonitrileGenerator
Mandelate nitrileGenerator
Mandelonitrile, (+-)-isomerHMDB
Chemical FormulaC8H7NO
Average Molecular Weight133.1473
Monoisotopic Molecular Weight133.052763851
IUPAC Name2-hydroxy-2-phenylacetonitrile
Traditional Namemandelonitrile
CAS Registry Number613-88-7
SMILES
OC(C#N)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H
InChI KeyNNICRUQPODTGRU-UHFFFAOYSA-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
  • Monocyclic benzene moiety
  • Alpha-hydroxynitrile
  • Secondary alcohol
  • Cyanohydrin
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point21.5 - 22 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.89 g/LALOGPS
logP0.68ALOGPS
logP0.95ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)11.8ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.02 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.68 m³·mol⁻¹ChemAxon
Polarizability13.55 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-2900000000-9bf5d9f7a830e077231eSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-2900000000-9bf5d9f7a830e077231eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-7900000000-f3c0c0e7a3df24b1f83bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0100-7900000000-11427484bfb13fd6a7a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-7c24126e874e537eb249Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05o0-0900000000-c346fce57e98f78257e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lfr-9700000000-228fb6b241946a8568d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-ea6e429426ef964cc081Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-4900000000-54d9f51720b51ca4117bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-4984b4790f404f8ab9c6Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a6r-9700000000-52314e45f42d178d3a85Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013191
KNApSAcK IDNot Available
Chemspider ID10304
KEGG Compound IDNot Available
BioCyc IDMANDELONITRILE
BiGG IDNot Available
Wikipedia LinkMandelonitrile
METLIN IDNot Available
PubChem Compound10758
PDB IDNot Available
ChEBI ID16910
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .