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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:24:17 UTC
Update Date2022-03-07 03:17:45 UTC
HMDB IDHMDB0060486
Secondary Accession Numbers
  • HMDB60486
Metabolite Identification
Common NameMandelonitrile
DescriptionMandelonitrile 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. Mandelonitrile is an extremely weak basic (essentially neutral) compound (based on its pKa). Mandelonitrile exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1563866066
Synonyms
ValueSource
(+)-MandelonitrileChEBI
(R)-(+)-MandelonitrileChEBI
D-MandelonitrileChEBI
Benzaldehyde cyanohydrinKegg
(R)-MandelonitrileKegg
Chemical FormulaC8H7NO
Average Molecular Weight133.1473
Monoisotopic Molecular Weight133.052763851
IUPAC Name(2R)-2-hydroxy-2-phenylacetonitrile
Traditional Name(-)-mandelonitrile
CAS Registry NumberNot Available
SMILES
O[C@@H](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/t8-/m0/s1
InChI KeyNNICRUQPODTGRU-QMMMGPOBSA-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 effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos128.87130932474
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.96131661259
DarkChem[M-H]-125.64631661259
DeepCCS[M+H]+128.90130932474
DeepCCS[M-H]-126.09830932474
DeepCCS[M-2H]-162.16930932474
DeepCCS[M+Na]+137.30830932474
AllCCS[M+H]+128.232859911
AllCCS[M+H-H2O]+123.532859911
AllCCS[M+NH4]+132.632859911
AllCCS[M+Na]+133.932859911
AllCCS[M-H]-125.432859911
AllCCS[M+Na-2H]-127.032859911
AllCCS[M+HCOO]-128.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MandelonitrileO[C@@H](C#N)C1=CC=CC=C12163.3Standard polar33892256
MandelonitrileO[C@@H](C#N)C1=CC=CC=C11264.3Standard non polar33892256
MandelonitrileO[C@@H](C#N)C1=CC=CC=C11285.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mandelonitrile,1TMS,isomer #1C[Si](C)(C)O[C@@H](C#N)C1=CC=CC=C11288.9Semi standard non polar33892256
Mandelonitrile,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H](C#N)C1=CC=CC=C11499.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mandelonitrile GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-7900000000-63735c13ec334fa809ee2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mandelonitrile GC-MS (1 TMS) - 70eV, Positivesplash10-0100-7900000000-11427484bfb13fd6a7a92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mandelonitrile GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mandelonitrile 10V, Positive-QTOFsplash10-001i-0900000000-8cf5145ba5004cd7bb812017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mandelonitrile 20V, Positive-QTOFsplash10-05o0-0900000000-5e06bfde5bdcc96f38962017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mandelonitrile 40V, Positive-QTOFsplash10-0mmj-9400000000-c916686bb130eeff008d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mandelonitrile 10V, Negative-QTOFsplash10-001i-0900000000-6297236be9bcd46fc8632017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mandelonitrile 20V, Negative-QTOFsplash10-003r-4900000000-ed4bbee965e6623f6aa12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mandelonitrile 40V, Negative-QTOFsplash10-004i-9100000000-732942c55dfb450c7cdd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mandelonitrile 10V, Positive-QTOFsplash10-014i-0900000000-ff2f50a1cd0316c3889d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mandelonitrile 20V, Positive-QTOFsplash10-014i-2900000000-e7674fcadf80c742e74d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mandelonitrile 40V, Positive-QTOFsplash10-02t9-9200000000-ee74ae1e15bd8bae88522021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mandelonitrile 10V, Negative-QTOFsplash10-001i-4900000000-6f591a5616423a7c26c52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mandelonitrile 20V, Negative-QTOFsplash10-0059-9600000000-f4b4bc42937e4ce43fd62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mandelonitrile 40V, Negative-QTOFsplash10-0kdi-6900000000-95f96f3606696317faf92021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00561
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMandelonitrile
METLIN IDNot Available
PubChem Compound9548674
PDB IDNot Available
ChEBI ID18450
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 References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:
GBA3
Uniprot ID:
Q9H227
Molecular weight:
Not Available
Reactions
Prunasin + Water → Mandelonitrile + D-Glucosedetails