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Showing metabocard for Acetone cyanohydrin (HMDB0060427)

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enzymes (1) Show 1 protein
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:02:05 UTC
Update Date2023-02-21 17:29:58 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 ). Crushing the tubers releases these compounds and produces acetone cyanohydrin. It is used as a surrogate in place of HCN, as illustrated by this synthesis of lithium cyanide:(CH3)2C(OH)CN + LiH → (CH3)2CO + LiCN + H2In transhydrocyanation, an equivalent of HCN is transferred from acetone cyanohydrin to another acceptor, with acetone as byproduct. The transfer is an equilibrium process, initiated by base. Treated with sulfuric acid give the sulfate ester of the methacrylamide, methanolysis of which gives ammonium bisulfate and methyl methacrylate. Acetone cyanohydrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetone cyanohydrin is classified as an extremely hazardous substance in the US Emergency Planning and Community Right-to-Know Act. 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 oregon yampahs, lowbush blueberries, common sages, grapefruits, and chicories. This could make acetone cyanohydrin a potential biomarker for the consumption of these foods. It liberates hydrogen cyanide easily, so it is used as a source of such. Acetone cyanohydrin is a potentially toxic compound. Alternatively, a simplified procedure involves the action of sodium or potassium cyanide on the sodium bisulfite adduct of acetone prepared in situ.
Structure
Data?1677000598
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0060427 (Acetone cyanohydrin)


  Mrv1652305271900012D          

  6  5  0  0  0  0            999 V2000
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  3  0  0  0  0
M  END
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3D MOL for HMDB0060427 (Acetone cyanohydrin)

HMDB0060427
     RDKit          3D
Acetone cyanohydrin
 13 12  0  0  0  0  0  0  0  0999 V2000
    1.2206   -0.3747   -0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546    0.2296    0.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0404   -0.8153    0.5980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2995    1.0951    1.1586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6722    1.0108   -0.9757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1764    1.6288   -1.8241 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5136   -1.2440    0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1846   -0.6512   -1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0548    0.3719   -0.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0533   -0.6006    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1947   -0.7204    1.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7488   -1.8426    0.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6673    1.9126    0.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  3  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
M  END
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3D SDF for HMDB0060427 (Acetone cyanohydrin)


  Mrv1652305271900012D          

  6  5  0  0  0  0            999 V2000
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  3  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060427

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(O)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C4H7NO/c1-4(2,6)3-5/h6H,1-2H3

> <INCHI_KEY>
MWFMGBPGAXYFAR-UHFFFAOYSA-N

> <FORMULA>
C4H7NO

> <MOLECULAR_WEIGHT>
85.1045

> <EXACT_MASS>
85.052763851

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
8.810994273217865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-2-methylpropanenitrile

> <ALOGPS_LOGP>
-0.29

> <JCHEM_LOGP>
0.01888523466666675

> <ALOGPS_LOGS>
-0.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.7613209888939

> <JCHEM_PKA_STRONGEST_BASIC>
-3.777998199457806

> <JCHEM_POLAR_SURFACE_AREA>
44.019999999999996

> <JCHEM_REFRACTIVITY>
22.5324

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.60e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetone cyanohydrin

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0060427 (Acetone cyanohydrin)

HMDB0060427
     RDKit          3D
Acetone cyanohydrin
 13 12  0  0  0  0  0  0  0  0999 V2000
    1.2206   -0.3747   -0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546    0.2296    0.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0404   -0.8153    0.5980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2995    1.0951    1.1586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6722    1.0108   -0.9757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1764    1.6288   -1.8241 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5136   -1.2440    0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1846   -0.6512   -1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0548    0.3719   -0.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0533   -0.6006    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1947   -0.7204    1.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7488   -1.8426    0.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6673    1.9126    0.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  3  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
M  END
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PDB for HMDB0060427 (Acetone cyanohydrin)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.080   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.080   1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.080  -1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for HMDB0060427 (Acetone cyanohydrin)

COMPND    HMDB0060427
HETATM    1  C1  UNL     1       1.221  -0.375  -0.405  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.055   0.230   0.113  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.040  -0.815   0.598  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.300   1.095   1.159  1.00  0.00           O  
HETATM    5  C4  UNL     1      -0.672   1.011  -0.976  1.00  0.00           C  
HETATM    6  N1  UNL     1      -1.176   1.629  -1.824  1.00  0.00           N  
HETATM    7  H1  UNL     1       1.514  -1.244   0.234  1.00  0.00           H  
HETATM    8  H2  UNL     1       1.185  -0.651  -1.470  1.00  0.00           H  
HETATM    9  H3  UNL     1       2.055   0.372  -0.252  1.00  0.00           H  
HETATM   10  H4  UNL     1      -2.053  -0.601   0.144  1.00  0.00           H  
HETATM   11  H5  UNL     1      -1.195  -0.720   1.690  1.00  0.00           H  
HETATM   12  H6  UNL     1      -0.749  -1.843   0.297  1.00  0.00           H  
HETATM   13  H7  UNL     1       0.667   1.913   0.693  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3    4    5
CONECT    3   10   11   12
CONECT    4   13
CONECT    5    6    6    6
END
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SMILES for HMDB0060427 (Acetone cyanohydrin)

CC(C)(O)C#N
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INCHI for HMDB0060427 (Acetone cyanohydrin)

InChI=1S/C4H7NO/c1-4(2,6)3-5/h6H,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
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 effectNot Available
Disposition
Biological locationSource
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 PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+114.74631661259
DarkChem[M-H]-110.05431661259
DeepCCS[M+H]+124.17830932474
DeepCCS[M-H]-122.28330932474
DeepCCS[M-2H]-157.88630932474
DeepCCS[M+Na]+132.35730932474
AllCCS[M+H]+121.432859911
AllCCS[M+H-H2O]+117.032859911
AllCCS[M+NH4]+125.532859911
AllCCS[M+Na]+126.732859911
AllCCS[M-H]-125.032859911
AllCCS[M+Na-2H]-129.732859911
AllCCS[M+HCOO]-134.932859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.0.59 minutes32390414
Predicted by Siyang on May 30, 202210.6303 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.61 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1223.2 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid397.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid121.5 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid258.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid71.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid387.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid442.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)178.3 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid742.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid226.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid955.9 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid262.8 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid290.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate531.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA374.7 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water145.6 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Acetone cyanohydrinCC(C)(O)C#N1314.5Standard polar33892256
Acetone cyanohydrinCC(C)(O)C#N682.2Standard non polar33892256
Acetone cyanohydrinCC(C)(O)C#N729.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acetone cyanohydrin,1TMS,isomer #1CC(C)(C#N)O[Si](C)(C)C861.9Semi standard non polar33892256
Acetone cyanohydrin,1TBDMS,isomer #1CC(C)(C#N)O[Si](C)(C)C(C)(C)C1074.1Semi standard non polar33892256
Spectra
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 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

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