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Showing metabocard for N-Methylformamide (HMDB0001122)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:27 UTC
HMDB IDHMDB0001122
Secondary Accession Numbers
  • HMDB01122
Metabolite Identification
Common NameN-Methylformamide
DescriptionN-Methylformamide, also known as HCONHCH3 or NMF, 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). N-Methylformamide has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make N-methylformamide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on N-Methylformamide.
Structure
Data?1676999727
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001122 (N-Methylformamide)


  Mrv0541 02231218562D          

  4  3  0  0  0  0            999 V2000
   14.3009   -5.3214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0154   -5.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0154   -6.5589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5864   -5.7339    0.0000 C   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
  1  4  1  0  0  0  0
M  END
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3D MOL for HMDB0001122 (N-Methylformamide)

HMDB0001122
     RDKit          3D
N-Methylformamide
  9  8  0  0  0  0  0  0  0  0999 V2000
   -1.0795    0.1982    0.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291   -0.5121   -0.0243 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4156    0.0608    0.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5215    1.2445    0.4057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9114    1.0346    1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7585   -0.5177    0.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6245    0.4975   -0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0207   -1.5106   -0.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2869   -0.4953   -0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  3  9  1  0
M  END
Download

3D SDF for HMDB0001122 (N-Methylformamide)


  Mrv0541 02231218562D          

  4  3  0  0  0  0            999 V2000
   14.3009   -5.3214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0154   -5.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0154   -6.5589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5864   -5.7339    0.0000 C   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
  1  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001122

> <DATABASE_NAME>
hmdb

> <SMILES>
CNC=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)

> <INCHI_KEY>
ATHHXGZTWNVVOU-UHFFFAOYSA-N

> <FORMULA>
C2H5NO

> <MOLECULAR_WEIGHT>
59.0672

> <EXACT_MASS>
59.037113787

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
5.75540955627049

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-methylformamide

> <ALOGPS_LOGP>
-1.31

> <JCHEM_LOGP>
-0.8553109703333334

> <ALOGPS_LOGS>
0.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.54298091278144

> <JCHEM_PKA_STRONGEST_BASIC>
-0.842484936384209

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
14.8721

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.95e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylformamide

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0001122 (N-Methylformamide)

HMDB0001122
     RDKit          3D
N-Methylformamide
  9  8  0  0  0  0  0  0  0  0999 V2000
   -1.0795    0.1982    0.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291   -0.5121   -0.0243 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4156    0.0608    0.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5215    1.2445    0.4057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9114    1.0346    1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7585   -0.5177    0.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6245    0.4975   -0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0207   -1.5106   -0.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2869   -0.4953   -0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  3  9  1  0
M  END
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PDB for HMDB0001122 (N-Methylformamide)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      26.695  -9.933   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      28.029 -10.703   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      28.029 -12.243   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      25.361 -10.703   0.000  0.00  0.00           C+0
CONECT    1    2    4                                                       
CONECT    2    1    3                                                       
CONECT    3    2                                                            
CONECT    4    1                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for HMDB0001122 (N-Methylformamide)

COMPND    HMDB0001122
HETATM    1  C1  UNL     1      -1.079   0.198   0.319  1.00  0.00           C  
HETATM    2  N1  UNL     1       0.129  -0.512  -0.024  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.416   0.061   0.036  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.521   1.245   0.406  1.00  0.00           O  
HETATM    5  H1  UNL     1      -0.911   1.035   1.017  1.00  0.00           H  
HETATM    6  H2  UNL     1      -1.759  -0.518   0.855  1.00  0.00           H  
HETATM    7  H3  UNL     1      -1.624   0.498  -0.598  1.00  0.00           H  
HETATM    8  H4  UNL     1       0.021  -1.511  -0.334  1.00  0.00           H  
HETATM    9  H5  UNL     1       2.287  -0.495  -0.226  1.00  0.00           H  
CONECT    1    2    5    6    7
CONECT    2    3    8
CONECT    3    4    4    9
END
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SMILES for HMDB0001122 (N-Methylformamide)

CNC=O
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INCHI for HMDB0001122 (N-Methylformamide)

InChI=1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
HCONHCH3ChEBI
MethylformamideChEBI
MonomethylformamideChEBI
N-Methyl-formamideChEBI
N-MonomethylformamideChEBI
NMFChEBI
N-MethylformamideKEGG
Chemical FormulaC2H5NO
Average Molecular Weight59.0672
Monoisotopic Molecular Weight59.037113787
IUPAC NameN-methylformamide
Traditional Namemethylformamide
CAS Registry Number123-39-7
SMILES
CNC=O
InChI Identifier
InChI=1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)
InChI KeyATHHXGZTWNVVOU-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
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • 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 locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-3.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 25 °CNot Available
LogP-0.97HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility395 g/LALOGPS
logP-1.3ALOGPS
logP-0.86ChemAxon
logS0.83ALOGPS
pKa (Strongest Acidic)16.54ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity14.87 m³·mol⁻¹ChemAxon
Polarizability5.76 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]+115.93530932474
DeepCCS[M-H]-114.09830932474
DeepCCS[M-2H]-149.3830932474
DeepCCS[M+Na]+123.15630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-MethylformamideCNC=O1519.7Standard polar33892256
N-MethylformamideCNC=O726.5Standard non polar33892256
N-MethylformamideCNC=O754.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Methylformamide,1TMS,isomer #1CN(C=O)[Si](C)(C)C858.6Semi standard non polar33892256
N-Methylformamide,1TMS,isomer #1CN(C=O)[Si](C)(C)C853.8Standard non polar33892256
N-Methylformamide,1TMS,isomer #1CN(C=O)[Si](C)(C)C1041.1Standard polar33892256
N-Methylformamide,1TBDMS,isomer #1CN(C=O)[Si](C)(C)C(C)(C)C1028.0Semi standard non polar33892256
N-Methylformamide,1TBDMS,isomer #1CN(C=O)[Si](C)(C)C(C)(C)C1048.7Standard non polar33892256
N-Methylformamide,1TBDMS,isomer #1CN(C=O)[Si](C)(C)C(C)(C)C1182.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - N-Methylformamide EI-B (Non-derivatized)splash10-057i-9000000000-60a7888b3706e6c01b2b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Methylformamide EI-B (Non-derivatized)splash10-057i-9000000000-60a7888b3706e6c01b2b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Methylformamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-9000000000-3d1c6f14cce05319e7652017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Methylformamide 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 - N-Methylformamide 10V, Positive-QTOFsplash10-03di-9000000000-efef2ef9adab060d99682016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylformamide 20V, Positive-QTOFsplash10-03e9-9000000000-d4d4c6894b8830773c2a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylformamide 40V, Positive-QTOFsplash10-001i-9000000000-ef803f2a7190446810872016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylformamide 10V, Negative-QTOFsplash10-0a6r-9000000000-dbaf66b4271f4f119f542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylformamide 20V, Negative-QTOFsplash10-0a6u-9000000000-82e7cd4cf5be3df7dced2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylformamide 40V, Negative-QTOFsplash10-004l-9000000000-1e7aed11b63f593cd5872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylformamide 10V, Negative-QTOFsplash10-0a4i-9000000000-0d3d5066ba65a1714c212021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylformamide 20V, Negative-QTOFsplash10-0a4i-9000000000-439ede5503e5f8b2f4fc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylformamide 40V, Negative-QTOFsplash10-0006-9000000000-90726b17dc36e29c52992021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylformamide 10V, Positive-QTOFsplash10-03di-9000000000-14d0958d7f503100d0582021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylformamide 20V, Positive-QTOFsplash10-01ox-9000000000-8ff4d86e2c774ca6af182021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylformamide 40V, Positive-QTOFsplash10-0006-9000000000-ff7f2c935a022bb6caf62021-09-25Wishart 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 LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022436
KNApSAcK IDNot Available
Chemspider ID28994
KEGG Compound IDC11489
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Methylformamide
METLIN IDNot Available
PubChem Compound31254
PDB IDNot Available
ChEBI ID7438
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Shieh DB, Chen CC, Shih TS, Tai HM, Wei YH, Chang HY: Mitochondrial DNA alterations in blood of the humans exposed to N,N-dimethylformamide. Chem Biol Interact. 2007 Feb 20;165(3):211-9. Epub 2006 Dec 20. [PubMed:17254560 ]
  2. Mraz J, Cimlova J, Stransky V, Nohova H, Kicova R, Simek P: N-Methylcarbamoyl-lysine adduct in globin: a new metabolic product and potential biomarker of N, N-dimethylformamide in humans. Toxicol Lett. 2006 Apr 10;162(2-3):211-8. Epub 2005 Nov 14. [PubMed:16289959 ]