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Showing metabocard for N-Ethylmaleamic acid (HMDB0255136)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 14:42:29 UTC
Update Date2021-09-26 23:09:43 UTC
HMDB IDHMDB0255136
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Ethylmaleamic acid
DescriptionN-Ethylmaleamic acid, also known as N-ethylmaleamate, belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage. Based on a literature review a small amount of articles have been published on N-Ethylmaleamic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-ethylmaleamic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-Ethylmaleamic acid 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 HMDB0255136 (N-Ethylmaleamic acid)


  Mrv1652309112116422D          

 10  9  0  0  0  0            999 V2000
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 N   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    1.4289    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
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3D MOL for HMDB0255136 (N-Ethylmaleamic acid)

HMDB0255136
     RDKit          3D
N-Ethylmaleamic acid
 19 18  0  0  0  0  0  0  0  0999 V2000
   -3.4861    0.6944   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5252   -0.2868    0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1882    0.1947   -0.1314 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0251   -0.4636    0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1298   -1.5232    0.9483 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2921    0.0739    0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3981   -0.5267    0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6824    0.0635    0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7508    1.1367   -0.5087 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8376   -0.5652    0.5623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7053    0.3134   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4548    0.7368    0.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0087    1.6756   -0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7113   -0.3205    1.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6621   -1.3148   -0.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641    1.0828   -0.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280    1.0103   -0.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3702   -1.4593    1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2016   -1.3073   -0.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  6 17  1  0
  7 18  1  0
 10 19  1  0
M  END
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3D SDF for HMDB0255136 (N-Ethylmaleamic acid)


  Mrv1652309112116422D          

 10  9  0  0  0  0            999 V2000
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 N   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    1.4289    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255136

> <DATABASE_NAME>
hmdb

> <SMILES>
CCNC(=O)C=CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H9NO3/c1-2-7-5(8)3-4-6(9)10/h3-4H,2H2,1H3,(H,7,8)(H,9,10)

> <INCHI_KEY>
HBQGCOWNLUOCBU-UHFFFAOYSA-N

> <FORMULA>
C6H9NO3

> <MOLECULAR_WEIGHT>
143.142

> <EXACT_MASS>
143.058243154

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.035040862963204

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(ethylcarbamoyl)prop-2-enoic acid

> <ALOGPS_LOGP>
0.06

> <JCHEM_LOGP>
-0.2673729246666666

> <ALOGPS_LOGS>
-1.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.730930850538211

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6553559837935423

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6032573713960857

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
36.0745

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(ethylcarbamoyl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0255136 (N-Ethylmaleamic acid)

HMDB0255136
     RDKit          3D
N-Ethylmaleamic acid
 19 18  0  0  0  0  0  0  0  0999 V2000
   -3.4861    0.6944   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5252   -0.2868    0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1882    0.1947   -0.1314 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0251   -0.4636    0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1298   -1.5232    0.9483 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2921    0.0739    0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3981   -0.5267    0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6824    0.0635    0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7508    1.1367   -0.5087 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8376   -0.5652    0.5623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7053    0.3134   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4548    0.7368    0.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0087    1.6756   -0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7113   -0.3205    1.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6621   -1.3148   -0.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641    1.0828   -0.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280    1.0103   -0.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3702   -1.4593    1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2016   -1.3073   -0.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  6 17  1  0
  7 18  1  0
 10 19  1  0
M  END
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PDB for HMDB0255136 (N-Ethylmaleamic acid)

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       3.850   1.334   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0255136 (N-Ethylmaleamic acid)

COMPND    HMDB0255136
HETATM    1  C1  UNL     1      -3.486   0.694  -0.523  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.525  -0.287   0.108  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.188   0.195  -0.131  1.00  0.00           N  
HETATM    4  C3  UNL     1      -0.025  -0.464   0.312  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.130  -1.523   0.948  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.292   0.074   0.038  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.398  -0.527   0.444  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.682   0.063   0.137  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.751   1.137  -0.509  1.00  0.00           O  
HETATM   10  O3  UNL     1       4.838  -0.565   0.562  1.00  0.00           O  
HETATM   11  H1  UNL     1      -3.705   0.313  -1.562  1.00  0.00           H  
HETATM   12  H2  UNL     1      -4.455   0.737   0.013  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.009   1.676  -0.582  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.711  -0.320   1.212  1.00  0.00           H  
HETATM   15  H5  UNL     1      -2.662  -1.315  -0.284  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.064   1.083  -0.663  1.00  0.00           H  
HETATM   17  H7  UNL     1       1.428   1.010  -0.523  1.00  0.00           H  
HETATM   18  H8  UNL     1       2.370  -1.459   1.007  1.00  0.00           H  
HETATM   19  H9  UNL     1       5.202  -1.307  -0.004  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4   16
CONECT    4    5    5    6
CONECT    6    7    7   17
CONECT    7    8   18
CONECT    8    9    9   10
CONECT   10   19
END
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SMILES for HMDB0255136 (N-Ethylmaleamic acid)

CCNC(=O)C=CC(O)=O
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INCHI for HMDB0255136 (N-Ethylmaleamic acid)

InChI=1S/C6H9NO3/c1-2-7-5(8)3-4-6(9)10/h3-4H,2H2,1H3,(H,7,8)(H,9,10)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
N-EthylmaleamateGenerator
Chemical FormulaC6H9NO3
Average Molecular Weight143.142
Monoisotopic Molecular Weight143.058243154
IUPAC Name3-(ethylcarbamoyl)prop-2-enoic acid
Traditional Name3-(ethylcarbamoyl)prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
CCNC(=O)C=CC(O)=O
InChI Identifier
InChI=1S/C6H9NO3/c1-2-7-5(8)3-4-6(9)10/h3-4H,2H2,1H3,(H,7,8)(H,9,10)
InChI KeyHBQGCOWNLUOCBU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty amides
Direct ParentN-acyl amines
Alternative Parents
Substituents
  • N-acyl-amine
  • Straight chain fatty acid
  • Unsaturated fatty acid
  • Fatty acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • 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
logP0.06ALOGPS
logP-0.27ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.66ChemAxon
pKa (Strongest Basic)-0.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity36.07 m³·mol⁻¹ChemAxon
Polarizability14.04 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]+126.73830932474
DeepCCS[M-H]-123.62230932474
DeepCCS[M-2H]-160.14830932474
DeepCCS[M+Na]+135.29930932474
AllCCS[M+H]+133.032859911
AllCCS[M+H-H2O]+128.932859911
AllCCS[M+NH4]+136.832859911
AllCCS[M+Na]+137.832859911
AllCCS[M-H]-130.232859911
AllCCS[M+Na-2H]-132.532859911
AllCCS[M+HCOO]-135.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Ethylmaleamic acidCCNC(=O)C=CC(O)=O2609.1Standard polar33892256
N-Ethylmaleamic acidCCNC(=O)C=CC(O)=O1558.4Standard non polar33892256
N-Ethylmaleamic acidCCNC(=O)C=CC(O)=O1552.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Ethylmaleamic acid,2TMS,isomer #1CCN(C(=O)C=CC(=O)O[Si](C)(C)C)[Si](C)(C)C1564.3Semi standard non polar33892256
N-Ethylmaleamic acid,2TMS,isomer #1CCN(C(=O)C=CC(=O)O[Si](C)(C)C)[Si](C)(C)C1615.1Standard non polar33892256
N-Ethylmaleamic acid,2TMS,isomer #1CCN(C(=O)C=CC(=O)O[Si](C)(C)C)[Si](C)(C)C1638.6Standard polar33892256
N-Ethylmaleamic acid,2TBDMS,isomer #1CCN(C(=O)C=CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2018.4Semi standard non polar33892256
N-Ethylmaleamic acid,2TBDMS,isomer #1CCN(C(=O)C=CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2002.0Standard non polar33892256
N-Ethylmaleamic acid,2TBDMS,isomer #1CCN(C(=O)C=CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1913.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Ethylmaleamic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9100000000-b16edf00a4a05039cef72021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Ethylmaleamic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Ethylmaleamic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Ethylmaleamic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Ethylmaleamic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Ethylmaleamic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-04Wishart 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 ID88719
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound98249
PDB IDNot Available
ChEBI ID140429
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 ]