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Showing NP-Card for Formamide (NP0000527)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:40:17 UTC
NP-MRD IDNP0000527
Secondary Accession NumbersNone
Natural Product Identification
Common NameFormamide
DescriptionFormamide, also known as methanamide or ameisensaeureamid, belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group). Formamide, in its pure state, has been used as an alternative solvent for the electrostatic self-assembly of polymer nanofilms. Formamide exists in all living organisms, ranging from bacteria to humans. Formamide has been detected, but not quantified in several different foods, such as hyssops, rose hips, asian pears, brassicas, and green bell peppers. It has been used as a softener for paper and fiber. Inhalation of large amounts of formamide vapor may require medical attention. In the past, formamide was produced by treating formic acid with ammonia, which produces ammonium formate, which in turn yields formamide upon heating:HCOOH + NH3 → HCOO−NH+4HCOO−NH+4 → HCONH2 + H2O. Formamide is also generated by aminolysis of ethyl formate: HCOOCH2CH3 + NH3 → HCONH2 + CH3CH2OH. The current industrial process for the manufacture of formamide involves either the carbonylation of ammonia: CO + NH3 → HCONH2. An alternative two-stage process involves the ammonolysis of methyl formate, which is formed from carbon monoxide and methanol: CO + CH3OH → HCOOCH3HCO2CH3 + NH3 → HCONH2 + CH3OH. Formamide is used in the industrial production of hydrogen cyanide. Formamide has been shown to exhibit hematoxicity in animals and is considered hazardous by prolonged exposure through inhalation, oral intake and dermal absorption.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000527 (Formamide)


  Mrv1652305271900122D          

  3  2  0  0  0  0            999 V2000
    0.0000    0.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -0.1366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7138   -0.1366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
M  END
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3D MOL for NP0000527 (Formamide)

HMDB0001536
     RDKit          3D
Formamide
  6  5  0  0  0  0  0  0  0  0999 V2000
    0.7029   -0.1101    0.1444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6672    0.0647   -0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767    1.0055    0.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4443    0.3531   -0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9038   -0.7155    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071   -0.5977   -0.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  1  4  1  0
  1  5  1  0
  2  6  1  0
M  END
Download

3D SDF for NP0000527 (Formamide)


  Mrv1652305271900122D          

  3  2  0  0  0  0            999 V2000
    0.0000    0.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -0.1366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7138   -0.1366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000527

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC=O

> <INCHI_IDENTIFIER>
InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3)

> <INCHI_KEY>
ZHNUHDYFZUAESO-UHFFFAOYSA-N

> <FORMULA>
CH3NO

> <MOLECULAR_WEIGHT>
45.0406

> <EXACT_MASS>
45.021463723

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
3.8305683658358256

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
formamide

> <ALOGPS_LOGP>
-1.53

> <JCHEM_LOGP>
-1.078987036

> <ALOGPS_LOGS>
1.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.669309876522544

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7073040777793448

> <JCHEM_POLAR_SURFACE_AREA>
43.09

> <JCHEM_REFRACTIVITY>
9.975399999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.03e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
formamide

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0000527 (Formamide)

HMDB0001536
     RDKit          3D
Formamide
  6  5  0  0  0  0  0  0  0  0999 V2000
    0.7029   -0.1101    0.1444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6672    0.0647   -0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767    1.0055    0.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4443    0.3531   -0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9038   -0.7155    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071   -0.5977   -0.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  1  4  1  0
  1  5  1  0
  2  6  1  0
M  END
Download

PDB for NP0000527 (Formamide)

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       0.000   0.517   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.332  -0.255   0.000  0.00  0.00           N+0
HETATM    3  O   UNK     0      -1.332  -0.255   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1                                                            
CONECT    3    1                                                            
MASTER        0    0    0    0    0    0    0    0    3    0    4    0
END
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3D PDB for NP0000527 (Formamide)

COMPND    HMDB0001536
HETATM    1  N1  UNL     1       0.703  -0.110   0.144  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.667   0.065  -0.186  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.277   1.005   0.390  1.00  0.00           O  
HETATM    4  H1  UNL     1       1.444   0.353  -0.415  1.00  0.00           H  
HETATM    5  H2  UNL     1       0.904  -0.715   0.960  1.00  0.00           H  
HETATM    6  H3  UNL     1      -1.107  -0.598  -0.893  1.00  0.00           H  
CONECT    1    2    4    5
CONECT    2    3    3    6
END
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SMILES for NP0000527 (Formamide)

NC=O
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INCHI for NP0000527 (Formamide)

InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3)
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View in JSmolView NMR Assignments
Synonyms
ValueSource
AmeisensaeureamidChEBI
CarbamaldehydeChEBI
FormamidChEBI
Formimidic acidChEBI
MethanamidChEBI
MethanamideChEBI
FormimidateGenerator
Chemical FormulaCH3NO
Average Mass45.0406 Da
Monoisotopic Mass45.02146 Da
IUPAC Nameformamide
Traditional Nameformamide
CAS Registry Number75-12-7
SMILES
NC=O
InChI Identifier
InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3)
InChI KeyZHNUHDYFZUAESO-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboximidic acids and derivatives
Sub ClassCarboximidic acids
Direct ParentCarboximidic acids
Alternative Parents
Substituents
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point2.55 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP-1.51Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility503 g/LALOGPS
logP-1.5ALOGPS
logP-1.1ChemAxon
logS1.05ALOGPS
pKa (Strongest Acidic)16.67ChemAxon
pKa (Strongest Basic)-0.71ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity9.98 m³·mol⁻¹ChemAxon
Polarizability3.83 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001536
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022677
KNApSAcK IDC00011920
Chemspider ID693
KEGG Compound IDC00488
BioCyc IDFORMAMIDE
BiGG IDNot Available
Wikipedia LinkFormamide
METLIN ID4182
PubChem Compound713
PDB IDNot Available
ChEBI ID16397
Good Scents IDrw1247401
References
General References
  1. Lareo AC, Perbellini L: Biological monitoring of workers exposed to N-N-dimethylformamide. II. Dimethylformamide and its metabolites in urine of exposed workers. Int Arch Occup Environ Health. 1995;67(1):47-52. [PubMed:7622279 ]
  2. Kawashima K, Doi H, Ito Y, Shibata MA, Yoshinaka R, Otsuki Y: Evaluation of cell death and proliferation in psoriatic epidermis. J Dermatol Sci. 2004 Sep;35(3):207-14. [PubMed:15381242 ]
  3. Major J, Hudak A, Kiss G, Jakab MG, Szaniszlo J, Naray M, Nagy I, Tompa A: Follow-up biological and genotoxicological monitoring of acrylonitrile- and dimethylformamide-exposed viscose rayon plant workers. Environ Mol Mutagen. 1998;31(4):301-10. [PubMed:9654238 ]
  4. Al-Soud WA, Ouis IS, Li DQ, Ljungh S, Wadstrom T: Characterization of the PCR inhibitory effect of bile to optimize real-time PCR detection of Helicobacter species. FEMS Immunol Med Microbiol. 2005 May 1;44(2):177-82. [PubMed:15866213 ]
  5. Eizuru Y, Minamishima Y, Matsumoto T, Hamakado T, Mizukoshi M, Nabeshima K, Koono M, Yoshida A, Yoshida H, Kikuchi M: Application of in situ hybridization with a novel phenytoin-labeled probe to conventional formalin-fixed, paraffin-embedded tissue sections. J Virol Methods. 1995 Apr;52(3):309-16. [PubMed:7601905 ]
  6. Walrath J, Fayerweather WE, Gilby PG, Pell S: A case-control study of cancer among du pont employees with potential for exposure to dimethylformamide. J Occup Med. 1989 May;31(5):432-8. [PubMed:2715850 ]