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Showing NP-Card for cyanoacetamide (NP0195678)

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Record Information
Version2.0
Created at2022-09-04 13:35:14 UTC
Updated at2022-09-04 13:35:14 UTC
NP-MRD IDNP0195678
Secondary Accession NumbersNone
Natural Product Identification
Common Namecyanoacetamide
DescriptionCyanoacetamide belongs to the class of organic compounds known as primary carboxylic acid amides. Primary carboxylic acid amides are compounds comprising primary carboxylic acid amide functional group, with the general structure RC(=O)NH2. Cyanoacetamide is an extremely weak basic (essentially neutral) compound (based on its pKa). Cyanoacetamide is a potentially toxic compound. Oxygen therapy can also be administered. Skin contact with cyanide salts can irritate and produce sores. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. It complexes with the ferric iron atom in this enzyme.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0195678 (cyanoacetamide)


  Mrv0541 02241205232D          

  6  5  0  0  0  0            999 V2000
    2.8875   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4289    0.0000 O   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
    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  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  3  0  0  0  0
M  END
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3D MOL for NP0195678 (cyanoacetamide)

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3D SDF for NP0195678 (cyanoacetamide)

  Mrv0541 02241205232D          

  6  5  0  0  0  0            999 V2000
    2.8875   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4289    0.0000 O   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
    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  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  3  0  0  0  0
M  END
> <DATABASE_ID>
NP0195678

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=O)CC#N

> <INCHI_IDENTIFIER>
InChI=1S/C3H4N2O/c4-2-1-3(5)6/h1H2,(H2,5,6)

> <INCHI_KEY>
DGJMPUGMZIKDRO-UHFFFAOYSA-N

> <FORMULA>
C3H4N2O

> <MOLECULAR_WEIGHT>
84.0767

> <EXACT_MASS>
84.03236276

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
7.477523465616764

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-cyanoacetamide

> <ALOGPS_LOGP>
-1.23

> <JCHEM_LOGP>
-1.0801110153333333

> <ALOGPS_LOGS>
-0.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.67464267749646

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.527349390736662

> <JCHEM_PKA_STRONGEST_BASIC>
-6.067700221168369

> <JCHEM_POLAR_SURFACE_AREA>
66.88

> <JCHEM_REFRACTIVITY>
19.789299999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.58e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetamide, 2-cyano-

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0195678 (cyanoacetamide)
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PDB for NP0195678 (cyanoacetamide)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0       5.390  -1.334   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.080  -2.667   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.080   0.000   0.000  0.00  0.00           C+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                                                  
CONECT    3    2                                                            
CONECT    4    2    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 NP0195678 (cyanoacetamide)
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SMILES for NP0195678 (cyanoacetamide)
NC(=O)CC#N
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INCHI for NP0195678 (cyanoacetamide)
InChI=1S/C3H4N2O/c4-2-1-3(5)6/h1H2,(H2,5,6)
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View in JSmol
SynonymsNot Available
Chemical FormulaC3H4N2O
Average Mass84.0767 Da
Monoisotopic Mass84.03236 Da
IUPAC Name2-cyanoacetamide
Traditional Nameacetamide, 2-cyano-
CAS Registry NumberNot Available
SMILES
NC(=O)CC#N
InChI Identifier
InChI=1S/C3H4N2O/c4-2-1-3(5)6/h1H2,(H2,5,6)
InChI KeyDGJMPUGMZIKDRO-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as primary carboxylic acid amides. Primary carboxylic acid amides are compounds comprising primary carboxylic acid amide functional group, with the general structure RC(=O)NH2.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassCarboxylic acid derivatives  
Direct ParentPrimary carboxylic acid amides  
Alternative Parents
Substituents
  • Primary carboxylic acid amide
    • 

  • Nitrile
    • 

  • Carbonitrile
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
logP-1.2ALOGPS
logP-1.1ChemAxon
logS-0.51ALOGPS
pKa (Strongest Acidic)8.53ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.88 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity19.79 m³·mol⁻¹ChemAxon
Polarizability7.48 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCyanoacetamide  
METLIN IDNot Available
PubChem Compound7898  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]