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Showing metabocard for Maleimide (HMDB0254312)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 13:32:42 UTC
Update Date2022-11-23 22:29:16 UTC
HMDB IDHMDB0254312
Secondary Accession NumbersNone
Metabolite Identification
Common NameMaleimide
Descriptionmaleimide, also known as 2,5-pyrroledione, belongs to the class of organic compounds known as maleimides. Maleimides are compounds containing a 2,5-pyrroledione moiety. Based on a literature review very few articles have been published on maleimide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Maleimide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Maleimide 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 HMDB0254312 (Maleimide)


  Mrv1652305062021442D          

  7  7  0  0  0  0            999 V2000
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
M  END
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3D MOL for HMDB0254312 (Maleimide)

HMDB0254312
     RDKit          3D
MALEIMIDE
 10 10  0  0  0  0  0  0  0  0999 V2000
   -2.4310   -1.3178    0.2234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3431   -0.7349    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0950    0.6964    0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2044    0.8799   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8293   -0.4437   -0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2073   -0.6435   -0.3161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0567   -1.3606   -0.0429 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500    1.4636    0.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227    1.8224   -0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8123   -0.3619    0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  2  1  0
  3  8  1  0
  4  9  1  0
  6 10  1  0
M  END
Download

3D SDF for HMDB0254312 (Maleimide)


  Mrv1652305062021442D          

  7  7  0  0  0  0            999 V2000
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254312

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=NC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C4H3NO2/c6-3-1-2-4(7)5-3/h1-2H,(H,5,6,7)

> <INCHI_KEY>
PEEHTFAAVSWFBL-UHFFFAOYSA-N

> <FORMULA>
C4H3NO2

> <MOLECULAR_WEIGHT>
97.073

> <EXACT_MASS>
97.016378341

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
8.237887813478814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-2H-pyrrol-2-one

> <ALOGPS_LOGP>
-0.12

> <JCHEM_LOGP>
-0.2684021206666667

> <ALOGPS_LOGS>
-0.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.299878821234625

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0449658818934546

> <JCHEM_POLAR_SURFACE_AREA>
49.660000000000004

> <JCHEM_REFRACTIVITY>
23.673099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
maleimide

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0254312 (Maleimide)

HMDB0254312
     RDKit          3D
MALEIMIDE
 10 10  0  0  0  0  0  0  0  0999 V2000
   -2.4310   -1.3178    0.2234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3431   -0.7349    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0950    0.6964    0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2044    0.8799   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8293   -0.4437   -0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2073   -0.6435   -0.3161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0567   -1.3606   -0.0429 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500    1.4636    0.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227    1.8224   -0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8123   -0.3619    0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  2  1  0
  3  8  1  0
  4  9  1  0
  6 10  1  0
M  END
Download

PDB for HMDB0254312 (Maleimide)

HEADER    PROTEIN                                 06-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-20         0                                  
HETATM    1  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2    5    7                                                  
CONECT    5    3    4                                                       
CONECT    6    3                                                            
CONECT    7    4                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END
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3D PDB for HMDB0254312 (Maleimide)

COMPND    HMDB0254312
HETATM    1  O1  UNL     1      -2.431  -1.318   0.223  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.343  -0.735   0.086  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.095   0.696   0.022  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.204   0.880  -0.129  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.829  -0.444  -0.166  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.207  -0.643  -0.316  1.00  0.00           O  
HETATM    7  N1  UNL     1      -0.057  -1.361  -0.043  1.00  0.00           N  
HETATM    8  H1  UNL     1      -1.850   1.464   0.087  1.00  0.00           H  
HETATM    9  H2  UNL     1       0.723   1.822  -0.211  1.00  0.00           H  
HETATM   10  H3  UNL     1       2.812  -0.362   0.447  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7
CONECT    3    4    4    8
CONECT    4    5    9
CONECT    5    6    7    7
CONECT    6   10
END
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SMILES for HMDB0254312 (Maleimide)

OC1=NC(=O)C=C1
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INCHI for HMDB0254312 (Maleimide)

InChI=1S/C4H3NO2/c6-3-1-2-4(7)5-3/h1-2H,(H,5,6,7)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2,5-PyrroledioneChEBI
Maleic imideChEBI
MaleimideMeSH
Maleimide, potassium, silver (+1) (2:1:1) saltMeSH
Maleimide, silver (+1) saltMeSH
Chemical FormulaC4H3NO2
Average Molecular Weight97.073
Monoisotopic Molecular Weight97.016378341
IUPAC Name5-hydroxy-2H-pyrrol-2-one
Traditional Namemaleimide
CAS Registry NumberNot Available
SMILES
OC1=NC(=O)C=C1
InChI Identifier
InChI=1S/C4H3NO2/c6-3-1-2-4(7)5-3/h1-2H,(H,5,6,7)
InChI KeyPEEHTFAAVSWFBL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as maleimides. Maleimides are compounds containing a 2,5-pyrroledione moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassPyrrolidones
Direct ParentMaleimides
Alternative Parents
Substituents
  • Maleimide
  • Carboxylic acid imide
  • Dicarboximide
  • Carboxylic acid imide, n-unsubstituted
  • Pyrroline
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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-0.12ALOGPS
logP-0.27ChemAxon
logS-0.59ALOGPS
pKa (Strongest Acidic)5.3ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.66 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity23.67 m³·mol⁻¹ChemAxon
Polarizability8.24 ųChemAxon
Number of Rings1ChemAxon
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]+117.76130932474
DeepCCS[M-H]-114.74930932474
DeepCCS[M-2H]-151.42730932474
DeepCCS[M+Na]+126.27630932474
AllCCS[M+H]+120.132859911
AllCCS[M+H-H2O]+115.032859911
AllCCS[M+NH4]+124.832859911
AllCCS[M+Na]+126.232859911
AllCCS[M-H]-115.632859911
AllCCS[M+Na-2H]-118.632859911
AllCCS[M+HCOO]-121.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MALEIMIDEOC1=NC(=O)C=C12191.7Standard polar33892256
MALEIMIDEOC1=NC(=O)C=C11114.2Standard non polar33892256
MALEIMIDEOC1=NC(=O)C=C11069.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Maleimide GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-9000000000-79ce5a0e6951be6c49e92021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Maleimide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Maleimide GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Maleimide GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleimide 10V, Positive-QTOFsplash10-0002-9000000000-75d185e676baa20e09502016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleimide 20V, Positive-QTOFsplash10-0002-9000000000-56d709cd35b6a12bceeb2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleimide 40V, Positive-QTOFsplash10-0002-9000000000-8681f34b313b52130c812016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleimide 10V, Negative-QTOFsplash10-0002-9000000000-d2fa7092d69ae157f8792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleimide 20V, Negative-QTOFsplash10-0002-9000000000-47620f5e67024387e2d82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleimide 40V, Negative-QTOFsplash10-0005-9000000000-fc31a721dfde5531aa292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleimide 10V, Positive-QTOFsplash10-0002-9000000000-1597561c5a03bdcf0d4e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleimide 20V, Positive-QTOFsplash10-052b-9000000000-a1d03a717c298c9e42de2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleimide 40V, Positive-QTOFsplash10-0006-9000000000-3f0907e4678cf5ec1bf22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleimide 10V, Negative-QTOFsplash10-0002-9000000000-6d86d5a02c11617543162021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleimide 20V, Negative-QTOFsplash10-0002-9000000000-f37ac2c4900861a9a17e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleimide 40V, Negative-QTOFsplash10-0006-9000000000-90726b17dc36e29c52992021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-25Wishart 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 IDC00027734
Chemspider ID10471
KEGG Compound IDC07272
BioCyc IDMALEIMIDE
BiGG IDNot Available
Wikipedia LinkMaleimide
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID16072
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 ]