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Showing NP-Card for Pentanenitrile (NP0049577)

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Record Information
Version2.0
Created at2022-03-17 21:14:43 UTC
Updated at2022-03-17 21:14:43 UTC
NP-MRD IDNP0049577
Secondary Accession NumbersNone
Natural Product Identification
Common NamePentanenitrile
DescriptionPentanenitrile, also known as 1-butyl cyanide or 1-cyano-butane, 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. Pentanenitrile is possibly neutral. Outside of the human body, Pentanenitrile has been detected, but not quantified in, brassicas and corns. This could make pentanenitrile a potential biomarker for the consumption of these foods. Pentanenitrile can be produced by heating 1-chlorobutane with sodium cyanide in dimethyl sulfoxide. Pentanenitrile, valeronitrile or butyl cyanide is a nitrile with the formula C4H9CN. The cyanide is detoxified and excreted in urine as thiocyanate. Pentanenitrile is contained in bone oil. Another way to get the substance is by heating butyraldehyde with hydroxylamine. These conformers are called anti-anti (30%), anti-gauche (46%), gauche-anti, gauche-gauche-cis, and gauche-gauche-trans. Pentanenitrile is toxic to animals, and produces its action by the liberation of cyanide by cytochrome P450. Pentanenitrile is found in Brassica spp. Pentanenitrile is hydrolyzed to valeric acid by the fungi Gibberella intermedia, Fusarium oxysporum, and Aspergillus niger in which it induces production of the nitrilase enzyme.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049577 (Pentanenitrile)


  Mrv0541 05061311402D          

  6  5  0  0  0  0            999 V2000
   -0.1914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.3020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  3  0  0  0  0
M  END
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3D MOL for NP0049577 (Pentanenitrile)

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3D SDF for NP0049577 (Pentanenitrile)

  Mrv0541 05061311402D          

  6  5  0  0  0  0            999 V2000
   -0.1914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.3020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  3  0  0  0  0
M  END
> <DATABASE_ID>
NP0049577

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC#N

> <INCHI_IDENTIFIER>
InChI=1S/C5H9N/c1-2-3-4-5-6/h2-4H2,1H3

> <INCHI_KEY>
RFFFKMOABOFIDF-UHFFFAOYSA-N

> <FORMULA>
C5H9N

> <MOLECULAR_WEIGHT>
83.1317

> <EXACT_MASS>
83.073499293

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
10.122576911666691

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pentanenitrile

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
1.4242763293333334

> <ALOGPS_LOGS>
-0.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
23.79

> <JCHEM_REFRACTIVITY>
25.4519

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.99e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
valeronitrile

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0049577 (Pentanenitrile)
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PDB for NP0049577 (Pentanenitrile)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -0.357  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.644  -2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.977  -1.334   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       6.311  -0.564   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    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 NP0049577 (Pentanenitrile)
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SMILES for NP0049577 (Pentanenitrile)
CCCCC#N
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INCHI for NP0049577 (Pentanenitrile)
InChI=1S/C5H9N/c1-2-3-4-5-6/h2-4H2,1H3
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View in JSmol
Synonyms
ValueSource
1-Butyl cyanideHMDB
1-Cyano-butaneHMDB
1-CyanobutaneHMDB
Butyl cyanideHMDB
N-Butyl cyanideHMDB
N-PentanenitrileHMDB
N-ValeronitrileHMDB
Pentanenitrile, 9ciHMDB
PentanonitrileHMDB
Valeronitrile, 8ciHMDB
Chemical FormulaC5H9N
Average Mass83.1317 Da
Monoisotopic Mass83.07350 Da
IUPAC Namepentanenitrile
Traditional Namevaleronitrile
CAS Registry Number110-59-8
SMILES
CCCCC#N
InChI Identifier
InChI=1S/C5H9N/c1-2-3-4-5-6/h2-4H2,1H3
InChI KeyRFFFKMOABOFIDF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Brassica spp.Plant
Zea mays L.FooDB
    • Carlos Macku, and Takayuki Shibamoto. Headspace volatile compounds formed from heated corn oil an...
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
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
logP1.1ALOGPS
logP1.42ChemAxon
logS-0.62ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.79 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.45 m³·mol⁻¹ChemAxon
Polarizability10.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040173  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019884  
KNApSAcK IDNot Available
Chemspider ID7770  
KEGG Compound IDNot Available
BioCyc IDCPD-8862  
BiGG IDNot Available
Wikipedia LinkPentanenitrile  
METLIN IDNot Available
PubChem Compound8061  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available