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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
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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

$$$$
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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
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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 locationSource
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
Predicted Chromatographic Properties
Spectra
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 ]