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Showing metabocard for Formamide (HMDB0001536)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:46 UTC
HMDB IDHMDB0001536
Secondary Accession Numbers
  • HMDB01536
Metabolite 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
Data?1676999746
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001536 (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
Download

3D MOL for HMDB0001536 (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 HMDB0001536 (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>
HMDB0001536

> <DATABASE_NAME>
hmdb

> <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

$$$$
Download

3D-SDF for HMDB0001536 (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 HMDB0001536 (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
Download

3D PDB for HMDB0001536 (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
Download

SMILES for HMDB0001536 (Formamide)

NC=O
Download

INCHI for HMDB0001536 (Formamide)

InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
AmeisensaeureamidChEBI
CarbamaldehydeChEBI
FormamidChEBI
Formimidic acidChEBI
MethanamidChEBI
MethanamideChEBI
FormimidateGenerator
Chemical FormulaCH3NO
Average Molecular Weight45.0406
Monoisotopic Molecular Weight45.021463723
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
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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point2.55 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP-1.51HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+113.47630932474
DeepCCS[M-H]-111.65430932474
DeepCCS[M-2H]-146.88830932474
DeepCCS[M+Na]+120.50130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FormamideNC=O1709.0Standard polar33892256
FormamideNC=O598.3Standard non polar33892256
FormamideNC=O709.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Formamide,1TMS,isomer #1C[Si](C)(C)NC=O837.9Semi standard non polar33892256
Formamide,1TMS,isomer #1C[Si](C)(C)NC=O839.0Standard non polar33892256
Formamide,1TMS,isomer #1C[Si](C)(C)NC=O1088.1Standard polar33892256
Formamide,2TMS,isomer #1C[Si](C)(C)N(C=O)[Si](C)(C)C968.1Semi standard non polar33892256
Formamide,2TMS,isomer #1C[Si](C)(C)N(C=O)[Si](C)(C)C966.9Standard non polar33892256
Formamide,2TMS,isomer #1C[Si](C)(C)N(C=O)[Si](C)(C)C1039.3Standard polar33892256
Formamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC=O1062.4Semi standard non polar33892256
Formamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC=O1011.7Standard non polar33892256
Formamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC=O1266.1Standard polar33892256
Formamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C=O)[Si](C)(C)C(C)(C)C1381.1Semi standard non polar33892256
Formamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C=O)[Si](C)(C)C(C)(C)C1355.6Standard non polar33892256
Formamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C=O)[Si](C)(C)C(C)(C)C1290.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Formamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9000000000-f6326cc6c67041284b522017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Formamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formamide 10V, Positive-QTOFsplash10-0002-9000000000-4a58cc52ed1f85a41b4c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formamide 20V, Positive-QTOFsplash10-0002-9000000000-52b8e3cce362934e1d522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formamide 40V, Positive-QTOFsplash10-004j-9000000000-32c53cf62ffc73e10c842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formamide 10V, Negative-QTOFsplash10-0006-9000000000-0a22a0222cfe33823b8b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formamide 20V, Negative-QTOFsplash10-0006-9000000000-2473e800b4396749f8872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formamide 40V, Negative-QTOFsplash10-004l-9000000000-3221c668103b22c85e422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formamide 10V, Positive-QTOFsplash10-0002-9000000000-e0e93b80e95c0e39a9852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formamide 20V, Positive-QTOFsplash10-0002-9000000000-e0e93b80e95c0e39a9852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formamide 40V, Positive-QTOFsplash10-0002-9000000000-a08824ab04647a23f4ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formamide 10V, Negative-QTOFsplash10-0006-9000000000-451c209790660c80803f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formamide 20V, Negative-QTOFsplash10-0006-9000000000-451c209790660c80803f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formamide 40V, Negative-QTOFsplash10-0006-9000000000-ab072a75b4f755c7548c2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Feces
Tissue Locations
  • Adrenal Gland
  • Epidermis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022677
KNApSAcK IDC00011920
Chemspider ID693
KEGG Compound IDC00488
BioCyc IDFORMAMIDE
BiGG IDNot Available
Wikipedia LinkFormamide
METLIN ID4182
PubChem Compound713
PDB IDNot Available
ChEBI ID16397
Food Biomarker OntologyNot Available
VMH IDFRMD
MarkerDB IDNot Available
Good Scents IDrw1247401
References
Synthesis ReferenceMagill, P. L. Formamide. Journal of Industrial and Engineering Chemistry (Washington, D. C.) (1934), 26 611-14.
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]