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Showing metabocard for Acetone cyanohydrin (HMDB0060427)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:02:05 UTC
Update Date2019-07-23 07:14:19 UTC
HMDB IDHMDB0060427
Secondary Accession Numbers
  • HMDB60427
Metabolite Identification
Common NameAcetone cyanohydrin
DescriptionAcetone cyanohydrin, also known as 2-methyllactonitrile, belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). Acetone cyanohydrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetone cyanohydrin exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Acetone cyanohydrin has been detected, but not quantified in, several different foods, such as sourdoughs, tea, american butterfish, broad beans, and tartary buckwheats. This could make acetone cyanohydrin a potential biomarker for the consumption of these foods. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Acetone cyanohydrin is a potentially toxic compound. It complexes with the ferric iron atom in this enzyme. Skin contact with cyanide salts can irritate and produce sores. Oxygen therapy can also be administered. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase.
Structure
Data?1563866059
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-HydroxyisobutyronitrileChEBI
2-MethyllactonitrileChEBI
Acetone cyanhydrinChEBI
Acetone-cyanohydrinChEBI
alpha-HydroxyisobutyronitrileChEBI
2-Hydroxy-2-methylpropanenitrileKegg
a-HydroxyisobutyronitrileGenerator
Α-hydroxyisobutyronitrileGenerator
AcetoncyanhydrineHMDB
Acetone cyanohydrin, 14C-labeledHMDB
Chemical FormulaC4H7NO
Average Molecular Weight85.1045
Monoisotopic Molecular Weight85.052763851
IUPAC Name2-hydroxy-2-methylpropanenitrile
Traditional Nameacetone cyanohydrin
CAS Registry NumberNot Available
SMILES
CC(C)(O)C#N
InChI Identifier
InChI=1S/C4H7NO/c1-4(2,6)3-5/h6H,1-2H3
InChI KeyMWFMGBPGAXYFAR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentTertiary alcohols
Alternative Parents
Substituents
  • Tertiary alcohol
  • Alpha-hydroxynitrile
  • Cyanohydrin
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Role

Environmental role:

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility26 g/LALOGPS
logP-0.29ALOGPS
logP0.019ChemAxon
logS-0.52ALOGPS
pKa (Strongest Acidic)12.76ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.53 m³·mol⁻¹ChemAxon
Polarizability8.81 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-770359d0721cdfdd25e7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fu-9300000000-c28dcd8adee9c59078bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-a225990200c17c1d5ec3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9000000000-033fac0cf5145b432726Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9000000000-08c60cd373cc9c8fca19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-2f152ee4137e9704b5dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-8f021cb12cf136adfbbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-9000000000-9744197fabb953390cf8Spectrum
MSMass Spectrum (Electron Ionization)splash10-006x-9000000000-9aa3eca8406a4215b9c3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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 IDDB02203
Phenol Explorer Compound IDNot Available
FooDB IDFDB030647
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02659
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetone cyanohydrin
METLIN IDNot Available
PubChem Compound6406
PDB IDNot Available
ChEBI ID15348
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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

Enzyme Details
1. Cytosolic beta-glucosidase
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
Linamarin + Water → Acetone cyanohydrin + D-Glucosedetails