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Showing metabocard for Acetonitrile (HMDB0061869)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:56:15 UTC
Update Date2023-02-21 17:30:28 UTC
HMDB IDHMDB0061869
Secondary Accession Numbers
  • HMDB61869
Metabolite Identification
Common NameAcetonitrile
DescriptionAcetonitrile, also known as CH3-C#N or cyanomethane, belongs to the class of organic compounds known as nitriles. Nitriles are compounds having the structure RC#N; thus C-substituted derivatives of hydrocyanic acid, HC#N. Acetonitrile is the chemical compound with the formula CH3CN. Acetonitrile is possibly neutral. Acetonitrile is a potentially toxic compound. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Skin contact with cyanide salts can irritate and produce sores. Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death.
Structure
Data?1677000628
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0061869 (Acetonitrile)


  Mrv1652305271900012D          

  3  2  0  0  0  0            999 V2000
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    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  3  0  0  0  0
M  END
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3D MOL for HMDB0061869 (Acetonitrile)

HMDB0061869
     RDKit          3D
Acetonitrile
  6  5  0  0  0  0  0  0  0  0999 V2000
   -0.4875    0.0048   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9766   -0.0013    0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1429   -0.0096    0.0176 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8680   -0.7649   -0.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9150   -0.2483    0.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8490    1.0193   -0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  3  0
  1  4  1  0
  1  5  1  0
  1  6  1  0
M  END
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3D SDF for HMDB0061869 (Acetonitrile)


  Mrv1652305271900012D          

  3  2  0  0  0  0            999 V2000
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    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  3  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061869

> <DATABASE_NAME>
hmdb

> <SMILES>
CC#N

> <INCHI_IDENTIFIER>
InChI=1S/C2H3N/c1-2-3/h1H3

> <INCHI_KEY>
WEVYAHXRMPXWCK-UHFFFAOYSA-N

> <FORMULA>
C2H3N

> <MOLECULAR_WEIGHT>
41.0519

> <EXACT_MASS>
41.026549101

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
4.270644783344594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
acetonitrile

> <ALOGPS_LOGP>
-0.04

> <JCHEM_LOGP>
-0.16539684766666665

> <ALOGPS_LOGS>
-0.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
23.79

> <JCHEM_REFRACTIVITY>
11.623000000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetonitrile

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0061869 (Acetonitrile)

HMDB0061869
     RDKit          3D
Acetonitrile
  6  5  0  0  0  0  0  0  0  0999 V2000
   -0.4875    0.0048   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9766   -0.0013    0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1429   -0.0096    0.0176 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8680   -0.7649   -0.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9150   -0.2483    0.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8490    1.0193   -0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  3  0
  1  4  1  0
  1  5  1  0
  1  6  1  0
M  END
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PDB for HMDB0061869 (Acetonitrile)

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       3.080   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       6.160   0.000   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2                                                            
MASTER        0    0    0    0    0    0    0    0    3    0    4    0
END
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3D PDB for HMDB0061869 (Acetonitrile)

COMPND    HMDB0061869
HETATM    1  C1  UNL     1      -0.487   0.005  -0.014  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.977  -0.001   0.004  1.00  0.00           C  
HETATM    3  N1  UNL     1       2.143  -0.010   0.018  1.00  0.00           N  
HETATM    4  H1  UNL     1      -0.868  -0.765  -0.729  1.00  0.00           H  
HETATM    5  H2  UNL     1      -0.915  -0.248   0.989  1.00  0.00           H  
HETATM    6  H3  UNL     1      -0.849   1.019  -0.267  1.00  0.00           H  
CONECT    1    2    4    5    6
CONECT    2    3    3    3
END
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SMILES for HMDB0061869 (Acetonitrile)

CC#N
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INCHI for HMDB0061869 (Acetonitrile)

InChI=1S/C2H3N/c1-2-3/h1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
CH3-C#NChEBI
CyanomethaneChEBI
EthanenitrileChEBI
MeCNChEBI
Methyl cyanideChEBI
NCMeChEBI
Acetonitrile, 3H-labeledHMDB
Acetonitrile, 1-(14)C-labeledHMDB
Chemical FormulaC2H3N
Average Molecular Weight41.0519
Monoisotopic Molecular Weight41.026549101
IUPAC Nameacetonitrile
Traditional Nameacetonitrile
CAS Registry Number75-05-8
SMILES
CC#N
InChI Identifier
InChI=1S/C2H3N/c1-2-3/h1H3
InChI KeyWEVYAHXRMPXWCK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitriles. Nitriles are compounds having the structure RC#N; thus C-substituted derivatives of hydrocyanic acid, HC#N.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassOrganic cyanides
Direct ParentNitriles
Alternative Parents
Substituents
  • Nitrile
  • Carbonitrile
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological location
ProcessNot Available
Role
Industrial applicationBiological role
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 Solubility26.1 g/LALOGPS
logP-0.04ALOGPS
logP-0.17ChemAxon
logS-0.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.79 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity11.62 m³·mol⁻¹ChemAxon
Polarizability4.27 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+112.81430932474
DeepCCS[M-H]-111.05930932474
DeepCCS[M-2H]-146.31330932474
DeepCCS[M+Na]+119.74330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AcetonitrileCC#N953.4Standard polar33892256
AcetonitrileCC#N398.7Standard non polar33892256
AcetonitrileCC#N418.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Acetonitrile EI-B (Non-derivatized)splash10-0006-9000000000-44611647c11b54cc181f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetonitrile EI-B (Non-derivatized)splash10-0006-9000000000-bf970518821dd2c060012017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetonitrile EI-B (Non-derivatized)splash10-0006-9000000000-6af7455c7bc61c9540702017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetonitrile EI-B (Non-derivatized)splash10-0006-9000000000-836514fd6b54edefa88e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetonitrile EI-B (Non-derivatized)splash10-0006-9000000000-44611647c11b54cc181f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetonitrile EI-B (Non-derivatized)splash10-0006-9000000000-bf970518821dd2c060012018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetonitrile EI-B (Non-derivatized)splash10-0006-9000000000-6af7455c7bc61c9540702018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetonitrile EI-B (Non-derivatized)splash10-0006-9000000000-836514fd6b54edefa88e2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetonitrile GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-6e1f4ab882eb15de33172017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetonitrile GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetonitrile GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-6fc27dfe150133064baf2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetonitrile 10V, Positive-QTOFsplash10-0006-9000000000-9f69695bfe2ad813c4682015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetonitrile 20V, Positive-QTOFsplash10-0006-9000000000-9f69695bfe2ad813c4682015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetonitrile 40V, Positive-QTOFsplash10-0006-9000000000-9f69695bfe2ad813c4682015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetonitrile 10V, Negative-QTOFsplash10-0006-9000000000-f33e0a1e80895824a9ef2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetonitrile 20V, Negative-QTOFsplash10-0006-9000000000-f33e0a1e80895824a9ef2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetonitrile 40V, Negative-QTOFsplash10-0006-9000000000-f33e0a1e80895824a9ef2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetonitrile 10V, Positive-QTOFsplash10-0006-9000000000-ff7f2c935a022bb6caf62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetonitrile 20V, Positive-QTOFsplash10-0006-9000000000-ff7f2c935a022bb6caf62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetonitrile 40V, Positive-QTOFsplash10-0006-9000000000-0e4372e3196a2c9f48fb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetonitrile 10V, Negative-QTOFsplash10-0006-9000000000-084674f982c41369c1842021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetonitrile 20V, Negative-QTOFsplash10-0006-9000000000-084674f982c41369c1842021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetonitrile 40V, Negative-QTOFsplash10-0006-9000000000-084674f982c41369c1842021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis		 details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetonitrile
METLIN IDNot Available
PubChem Compound6342
PDB IDNot Available
ChEBI ID38472
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. Hashimoto K: [Toxicology of acetonitrile]. Sangyo Igaku. 1991 Nov;33(6):463-74. [PubMed:1770614 ]
  2. Swanson JR, Krasselt WG: An acetonitrile-related death. J Forensic Sci. 1994 Jan;39(1):271-9. [PubMed:8113708 ]
  3. Strasser CE, Cronje S, Raubenheimer HG: (Acetonitrile-kappaN)penta-carbonyl-tungsten(0). Acta Crystallogr Sect E Struct Rep Online. 2011 Jun 1;67(Pt 6):m772. doi: 10.1107/S1600536811017879. Epub 2011 May 20. [PubMed:21754656 ]
  4. Seo DM, Boyle PD, Henderson WA: Tetra-kis(acetonitrile-kappaN)lithium hexa-fluoridophosphate acetonitrile monosolvate. Acta Crystallogr Sect E Struct Rep Online. 2011 Aug 1;67(Pt 8):m1148. doi: 10.1107/S1600536811027528. Epub 2011 Jul 30. [PubMed:22090907 ]
  5. Benmebarek S, Boudraa M, Bouacida S, Merazig H: 2-(2-Nitro-phenyl-sulfin-yl)acetonitrile. Acta Crystallogr Sect E Struct Rep Online. 2013 Mar 1;69(Pt 3):o432. doi: 10.1107/S1600536813004832. Epub 2013 Feb 23. [PubMed:23476603 ]
  6. Wikipedia [Link]
  7. Wikipedia [Link]
  8. August Van Gysel, Frans Soeterbroeck, Geert Vermeulen, 'Acetonitrile Recycling Process.' U.S. Patent US20080073201, issued March 27, 2008. [Link]
  9. Gisela Olive, Salvador Olive, 'Process for preparing acetonitrile.' U.S. Patent US4058548, issued February, 1976. [Link]
  10. Robert D. Presson, Hsin-Chih Wu, Edward J. Sockell, 'Continuous acetonitrile recovery process.' U.S. Patent US4362603, issued August, 1966. [Link]