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Showing metabocard for Maleamic Acid (HMDB0254310)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 13:32:33 UTC
Update Date2022-11-23 22:29:16 UTC
HMDB IDHMDB0254310
Secondary Accession NumbersNone
Metabolite Identification
Common NameMaleamic Acid
Description557-24-4 belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. 557-24-4 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 ). Maleamic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Maleamic 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 HMDB0254310 (Maleamic Acid)


  Mrv0541 04121502132D          

  8  7  0  0  0  0            999 V2000
    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  2  0  0  0  0
  4  2  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
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3D MOL for HMDB0254310 (Maleamic Acid)

HMDB0254310
     RDKit          3D
MALEAMIC ACID
 13 12  0  0  0  0  0  0  0  0999 V2000
   -2.7592    0.1894   -0.0185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253    0.2352    0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4973    0.5537    1.8757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3121   -0.0941   -0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -0.0791    0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0527   -0.4125   -0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9154   -0.7203   -1.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2911   -0.3834    0.3526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6434   -0.1546    0.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546    0.5296   -1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3728   -0.3705   -1.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9720    0.1863    1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7509    0.5203    0.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  4 11  1  0
  5 12  1  0
  8 13  1  0
M  END
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3D SDF for HMDB0254310 (Maleamic Acid)


  Mrv0541 04121502132D          

  8  7  0  0  0  0            999 V2000
    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  2  0  0  0  0
  4  2  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254310

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H5NO3/c5-3(6)1-2-4(7)8/h1-2H,(H2,5,6)(H,7,8)

> <INCHI_KEY>
FSQQTNAZHBEJLS-UHFFFAOYSA-N

> <FORMULA>
C4H5NO3

> <MOLECULAR_WEIGHT>
115.088

> <EXACT_MASS>
115.026943025

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
9.931028910201096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-carbamoylprop-2-enoic acid

> <ALOGPS_LOGP>
-1.00

> <JCHEM_LOGP>
-0.847856945

> <ALOGPS_LOGS>
-0.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.970225761798357

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.339559917876603

> <JCHEM_PKA_STRONGEST_BASIC>
-0.40875126188158417

> <JCHEM_POLAR_SURFACE_AREA>
80.39

> <JCHEM_REFRACTIVITY>
26.429199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.17e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-carbamoylprop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0254310 (Maleamic Acid)

HMDB0254310
     RDKit          3D
MALEAMIC ACID
 13 12  0  0  0  0  0  0  0  0999 V2000
   -2.7592    0.1894   -0.0185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253    0.2352    0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4973    0.5537    1.8757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3121   -0.0941   -0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -0.0791    0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0527   -0.4125   -0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9154   -0.7203   -1.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2911   -0.3834    0.3526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6434   -0.1546    0.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546    0.5296   -1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3728   -0.3705   -1.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9720    0.1863    1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7509    0.5203    0.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  4 11  1  0
  5 12  1  0
  8 13  1  0
M  END
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PDB for HMDB0254310 (Maleamic Acid)

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  N   UNK     0       3.850   1.334   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0254310 (Maleamic Acid)

COMPND    HMDB0254310
HETATM    1  N1  UNL     1      -2.759   0.189  -0.018  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.525   0.235   0.668  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.497   0.554   1.876  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.312  -0.094  -0.063  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.883  -0.079   0.491  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.053  -0.413  -0.273  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.915  -0.720  -1.485  1.00  0.00           O  
HETATM    8  O3  UNL     1       3.291  -0.383   0.353  1.00  0.00           O  
HETATM    9  H1  UNL     1      -3.643  -0.155   0.410  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.755   0.530  -1.021  1.00  0.00           H  
HETATM   11  H3  UNL     1      -0.373  -0.370  -1.126  1.00  0.00           H  
HETATM   12  H4  UNL     1       0.972   0.186   1.525  1.00  0.00           H  
HETATM   13  H5  UNL     1       3.751   0.520   0.399  1.00  0.00           H  
CONECT    1    2    9   10
CONECT    2    3    3    4
CONECT    4    5    5   11
CONECT    5    6   12
CONECT    6    7    7    8
CONECT    8   13
END
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SMILES for HMDB0254310 (Maleamic Acid)

NC(=O)C=CC(O)=O
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INCHI for HMDB0254310 (Maleamic Acid)

InChI=1S/C4H5NO3/c5-3(6)1-2-4(7)8/h1-2H,(H2,5,6)(H,7,8)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-Amino-4-oxobut-2-enoateGenerator
Maleamic acidMeSH
Maleic acid monoamideMeSH
Chemical FormulaC4H5NO3
Average Molecular Weight115.088
Monoisotopic Molecular Weight115.026943025
IUPAC Name3-carbamoylprop-2-enoic acid
Traditional Name3-carbamoylprop-2-enoic acid
CAS Registry NumberNot Available
SMILES
NC(=O)C=CC(O)=O
InChI Identifier
InChI=1S/C4H5NO3/c5-3(6)1-2-4(7)8/h1-2H,(H2,5,6)(H,7,8)
InChI KeyFSQQTNAZHBEJLS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentStraight chain fatty acids
Alternative Parents
Substituents
  • Straight chain fatty acid
  • Unsaturated fatty acid
  • Carboxamide group
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen 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
logP-1ALOGPS
logP-0.85ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)3.34ChemAxon
pKa (Strongest Basic)-0.41ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.43 m³·mol⁻¹ChemAxon
Polarizability9.93 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]+124.59330932474
DeepCCS[M-H]-121.78430932474
DeepCCS[M-2H]-158.15530932474
DeepCCS[M+Na]+133.0530932474
AllCCS[M+H]+126.932859911
AllCCS[M+H-H2O]+122.632859911
AllCCS[M+NH4]+130.932859911
AllCCS[M+Na]+132.132859911
AllCCS[M-H]-121.432859911
AllCCS[M+Na-2H]-124.632859911
AllCCS[M+HCOO]-128.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MALEAMIC ACIDNC(=O)C=CC(O)=O2131.2Standard polar33892256
MALEAMIC ACIDNC(=O)C=CC(O)=O1149.7Standard non polar33892256
MALEAMIC ACIDNC(=O)C=CC(O)=O1377.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
MALEAMIC ACID,2TMS,isomer #1C[Si](C)(C)NC(=O)C=CC(=O)O[Si](C)(C)C1549.4Semi standard non polar33892256
MALEAMIC ACID,2TMS,isomer #1C[Si](C)(C)NC(=O)C=CC(=O)O[Si](C)(C)C1713.6Standard non polar33892256
MALEAMIC ACID,2TMS,isomer #1C[Si](C)(C)NC(=O)C=CC(=O)O[Si](C)(C)C1696.7Standard polar33892256
MALEAMIC ACID,2TMS,isomer #2C[Si](C)(C)N(C(=O)C=CC(=O)O)[Si](C)(C)C1640.4Semi standard non polar33892256
MALEAMIC ACID,2TMS,isomer #2C[Si](C)(C)N(C(=O)C=CC(=O)O)[Si](C)(C)C1636.5Standard non polar33892256
MALEAMIC ACID,2TMS,isomer #2C[Si](C)(C)N(C(=O)C=CC(=O)O)[Si](C)(C)C1929.0Standard polar33892256
MALEAMIC ACID,3TMS,isomer #1C[Si](C)(C)OC(=O)C=CC(=O)N([Si](C)(C)C)[Si](C)(C)C1587.8Semi standard non polar33892256
MALEAMIC ACID,3TMS,isomer #1C[Si](C)(C)OC(=O)C=CC(=O)N([Si](C)(C)C)[Si](C)(C)C1616.7Standard non polar33892256
MALEAMIC ACID,3TMS,isomer #1C[Si](C)(C)OC(=O)C=CC(=O)N([Si](C)(C)C)[Si](C)(C)C1559.7Standard polar33892256
MALEAMIC ACID,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)C=CC(=O)O[Si](C)(C)C(C)(C)C2015.8Semi standard non polar33892256
MALEAMIC ACID,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)C=CC(=O)O[Si](C)(C)C(C)(C)C2111.4Standard non polar33892256
MALEAMIC ACID,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)C=CC(=O)O[Si](C)(C)C(C)(C)C1893.8Standard polar33892256
MALEAMIC ACID,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)C=CC(=O)O)[Si](C)(C)C(C)(C)C2084.1Semi standard non polar33892256
MALEAMIC ACID,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)C=CC(=O)O)[Si](C)(C)C(C)(C)C2064.6Standard non polar33892256
MALEAMIC ACID,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)C=CC(=O)O)[Si](C)(C)C(C)(C)C1981.4Standard polar33892256
MALEAMIC ACID,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2271.0Semi standard non polar33892256
MALEAMIC ACID,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2184.3Standard non polar33892256
MALEAMIC ACID,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1937.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Maleamic Acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-01bd-9100000000-e8416672a40d8c68a0e12021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Maleamic Acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Maleamic Acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Maleamic Acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Maleamic Acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Maleamic Acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleamic Acid 10V, Positive-QTOFsplash10-0002-9000000000-886dc1d144079a5b08882021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleamic Acid 20V, Positive-QTOFsplash10-000x-9000000000-5855262ab1d71bac67d32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleamic Acid 40V, Positive-QTOFsplash10-0006-9000000000-680cb912f04a3142f7182021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleamic Acid 10V, Negative-QTOFsplash10-0229-9700000000-ecf07b376a6fd940f6372021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleamic Acid 20V, Negative-QTOFsplash10-0006-9000000000-d149930ba09bca62dabd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleamic Acid 40V, Negative-QTOFsplash10-0006-9000000000-90726b17dc36e29c52992021-10-12Wishart 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 Compound11187
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 ]