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Showing metabocard for N,N-Dimethylacrylamide (HMDB0255259)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 14:51:07 UTC
Update Date2021-09-26 23:09:54 UTC
HMDB IDHMDB0255259
Secondary Accession NumbersNone
Metabolite Identification
Common NameN,N-Dimethylacrylamide
DescriptionN,N-Dimethylacrylamide, also known as dmaa-N,N, belongs to the class of organic compounds known as tertiary carboxylic acid amides. Tertiary carboxylic acid amides are compounds containing an amide derivative of carboxylic acid, with the general structure RN(R1)C(R2)=O (R1-R2 any atom but H). N,N-Dimethylacrylamide is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). N,n-dimethylacrylamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N,N-Dimethylacrylamide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0255259 (N,N-Dimethylacrylamide)


  Mrv1572004191603142D          

  7  6  0  0  0  0            999 V2000
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   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
    1.2375   -0.7145    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
    1.2375    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  2  0  0  0  0
M  END
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3D MOL for HMDB0255259 (N,N-Dimethylacrylamide)

HMDB0255259
     RDKit          3D
N,N-Dimethylacrylamide
 16 15  0  0  0  0  0  0  0  0999 V2000
    2.7260   -0.7725    0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4869   -0.7709    0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5967    0.3305    0.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9814    1.3043    1.2690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7427    0.3619    0.0901 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2150   -0.7320   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6529    1.4401    0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4083   -1.5885    0.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0536    0.0546    1.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1512   -1.5956   -0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4965   -0.9834   -1.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1711   -0.4585   -1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4775   -1.6175   -0.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4520    1.4686   -0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1339    1.1833    1.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0624    2.3755    0.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  6 11  1  0
  6 12  1  0
  6 13  1  0
  7 14  1  0
  7 15  1  0
  7 16  1  0
M  END
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3D SDF for HMDB0255259 (N,N-Dimethylacrylamide)


  Mrv1572004191603142D          

  7  6  0  0  0  0            999 V2000
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   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
    1.2375   -0.7145    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
    1.2375    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255259

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)C(=O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C5H9NO/c1-4-5(7)6(2)3/h4H,1H2,2-3H3

> <INCHI_KEY>
YLGYACDQVQQZSW-UHFFFAOYSA-N

> <FORMULA>
C5H9NO

> <MOLECULAR_WEIGHT>
99.133

> <EXACT_MASS>
99.068413914

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
10.840129867507397

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N,N-dimethylprop-2-enamide

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
0.1733568103333334

> <ALOGPS_LOGS>
0.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.40450904871543647

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
28.907

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N,N-dimethylacrylamide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0255259 (N,N-Dimethylacrylamide)

HMDB0255259
     RDKit          3D
N,N-Dimethylacrylamide
 16 15  0  0  0  0  0  0  0  0999 V2000
    2.7260   -0.7725    0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4869   -0.7709    0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5967    0.3305    0.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9814    1.3043    1.2690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7427    0.3619    0.0901 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2150   -0.7320   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6529    1.4401    0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4083   -1.5885    0.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0536    0.0546    1.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1512   -1.5956   -0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4965   -0.9834   -1.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1711   -0.4585   -1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4775   -1.6175   -0.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4520    1.4686   -0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1339    1.1833    1.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0624    2.3755    0.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  6 11  1  0
  6 12  1  0
  6 13  1  0
  7 14  1  0
  7 15  1  0
  7 16  1  0
M  END
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PDB for HMDB0255259 (N,N-Dimethylacrylamide)

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310  -1.334   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       2.310   1.334   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    6                                                            
CONECT    3    6                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    2    3    5                                                  
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0255259 (N,N-Dimethylacrylamide)

COMPND    HMDB0255259
HETATM    1  C1  UNL     1       2.726  -0.773   0.664  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.487  -0.771   0.219  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.597   0.331   0.553  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.981   1.304   1.269  1.00  0.00           O  
HETATM    5  N1  UNL     1      -0.743   0.362   0.090  1.00  0.00           N  
HETATM    6  C4  UNL     1      -1.215  -0.732  -0.729  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.653   1.440   0.403  1.00  0.00           C  
HETATM    8  H1  UNL     1       3.408  -1.588   0.425  1.00  0.00           H  
HETATM    9  H2  UNL     1       3.054   0.055   1.272  1.00  0.00           H  
HETATM   10  H3  UNL     1       1.151  -1.596  -0.391  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.497  -0.983  -1.534  1.00  0.00           H  
HETATM   12  H5  UNL     1      -2.171  -0.459  -1.264  1.00  0.00           H  
HETATM   13  H6  UNL     1      -1.478  -1.617  -0.106  1.00  0.00           H  
HETATM   14  H7  UNL     1      -2.452   1.469  -0.342  1.00  0.00           H  
HETATM   15  H8  UNL     1      -2.134   1.183   1.386  1.00  0.00           H  
HETATM   16  H9  UNL     1      -1.062   2.376   0.481  1.00  0.00           H  
CONECT    1    2    2    8    9
CONECT    2    3   10
CONECT    3    4    4    5
CONECT    5    6    7
CONECT    6   11   12   13
CONECT    7   14   15   16
END
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SMILES for HMDB0255259 (N,N-Dimethylacrylamide)

CN(C)C(=O)C=C
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INCHI for HMDB0255259 (N,N-Dimethylacrylamide)

InChI=1S/C5H9NO/c1-4-5(7)6(2)3/h4H,1H2,2-3H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
DMAA-N,NMeSH
N,N-DimethylacrylamideMeSH
Chemical FormulaC5H9NO
Average Molecular Weight99.133
Monoisotopic Molecular Weight99.068413914
IUPAC NameN,N-dimethylprop-2-enamide
Traditional NameN,N-dimethylacrylamide
CAS Registry NumberNot Available
SMILES
CN(C)C(=O)C=C
InChI Identifier
InChI=1S/C5H9NO/c1-4-5(7)6(2)3/h4H,1H2,2-3H3
InChI KeyYLGYACDQVQQZSW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tertiary carboxylic acid amides. Tertiary carboxylic acid amides are compounds containing an amide derivative of carboxylic acid, with the general structure RN(R1)C(R2)=O (R1-R2 any atom but H).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentTertiary carboxylic acid amides
Alternative Parents
Substituents
  • Acrylic acid or derivatives
  • Tertiary carboxylic acid amide
  • 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
Ontology
Physiological effectNot Available
Disposition
Biological location
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0.17ALOGPS
logP0.17ChemAxon
logS0.25ALOGPS
pKa (Strongest Basic)-0.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.91 m³·mol⁻¹ChemAxon
Polarizability10.84 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]+120.77530932474
DeepCCS[M-H]-118.1530932474
DeepCCS[M-2H]-154.54330932474
DeepCCS[M+Na]+129.19430932474
AllCCS[M+H]+125.932859911
AllCCS[M+H-H2O]+121.632859911
AllCCS[M+NH4]+129.932859911
AllCCS[M+Na]+131.132859911
AllCCS[M-H]-125.032859911
AllCCS[M+Na-2H]-129.032859911
AllCCS[M+HCOO]-133.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N,N-DimethylacrylamideCN(C)C(=O)C=C1386.8Standard polar33892256
N,N-DimethylacrylamideCN(C)C(=O)C=C821.4Standard non polar33892256
N,N-DimethylacrylamideCN(C)C(=O)C=C938.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N,N-Dimethylacrylamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9000000000-ff7ce7496f1ea219b2752021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N,N-Dimethylacrylamide 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,N-Dimethylacrylamide 10V, Positive-QTOFsplash10-0udi-3900000000-d4342e07739631a8ac812016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylacrylamide 20V, Positive-QTOFsplash10-0zfr-8900000000-f35c17c1990b040772b02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylacrylamide 40V, Positive-QTOFsplash10-0a4i-9000000000-351acb5ee4ecc811b0d62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylacrylamide 10V, Negative-QTOFsplash10-0002-9000000000-fc853cd85b91efbed1cb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylacrylamide 20V, Negative-QTOFsplash10-0f6t-9000000000-556f8f035333019f2cf02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylacrylamide 40V, Negative-QTOFsplash10-0zfr-9000000000-0b120b5a5669d8a5076b2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound17587
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]