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Showing metabocard for N-Chlorosuccinimide (HMDB0255101)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 14:39:37 UTC
Update Date2022-11-23 22:29:17 UTC
HMDB IDHMDB0255101
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Chlorosuccinimide
DescriptionN-chlorosuccinimide, also known as succinchlorimide or NCS, belongs to the class of organic compounds known as pyrrolidine-2-ones. These are pyrrolidines which bear a C=O group at position 2 of the pyrrolidine ring. N-chlorosuccinimide is an extremely weak acidic (essentially neutral) compound (based on its pKa). A five-membered cyclic dicarboximide compound having a chloro substituent on the nitrogen atom. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-chlorosuccinimide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-Chlorosuccinimide 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 HMDB0255101 (N-Chlorosuccinimide)

  Mrv1572004221604152D          

  8  8  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
   -0.8843    0.8843    0.0000 Cl  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  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
M  END
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3D MOL for HMDB0255101 (N-Chlorosuccinimide)

HMDB0255101
     RDKit          3D
N-CHLOROSUCCINIMIDE
 12 12  0  0  0  0  0  0  0  0999 V2000
    1.0762   -2.2610    0.0685 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5944   -1.1140    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8531   -0.7266    0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8866    0.5479   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3612    1.2084   -0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5663    2.4338    0.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817    0.1367    0.1325 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0046    0.3100    0.2895 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0478   -0.4327    1.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -1.4978   -0.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7835    0.2384   -1.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820    1.1569   -0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  2  1  0
  3  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
M  END
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3D SDF for HMDB0255101 (N-Chlorosuccinimide)

  Mrv1572004221604152D          

  8  8  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
   -0.8843    0.8843    0.0000 Cl  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  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255101

> <DATABASE_NAME>
hmdb

> <SMILES>
ClN1C(=O)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2

> <INCHI_KEY>
JRNVZBWKYDBUCA-UHFFFAOYSA-N

> <FORMULA>
C4H4ClNO2

> <MOLECULAR_WEIGHT>
133.53

> <EXACT_MASS>
132.9930561

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
10.987650080735735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-chloropyrrolidine-2,5-dione

> <ALOGPS_LOGP>
-2.15

> <JCHEM_LOGP>
-0.2312569766666666

> <ALOGPS_LOGS>
-0.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.077679791022607

> <JCHEM_POLAR_SURFACE_AREA>
37.38

> <JCHEM_REFRACTIVITY>
27.617700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chlorosuccinimide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0255101 (N-Chlorosuccinimide)

HMDB0255101
     RDKit          3D
N-CHLOROSUCCINIMIDE
 12 12  0  0  0  0  0  0  0  0999 V2000
    1.0762   -2.2610    0.0685 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5944   -1.1140    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8531   -0.7266    0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8866    0.5479   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3612    1.2084   -0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5663    2.4338    0.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817    0.1367    0.1325 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0046    0.3100    0.2895 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0478   -0.4327    1.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -1.4978   -0.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7835    0.2384   -1.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820    1.1569   -0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  2  1  0
  3  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
M  END
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PDB for HMDB0255101 (N-Chlorosuccinimide)

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         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 Cl   UNK     0      -1.651   1.651   0.000  0.00  0.00          Cl+0
HETATM    6  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM    8  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    6    7                                                  
CONECT    4    2    6    8                                                  
CONECT    5    6                                                            
CONECT    6    3    4    5                                                  
CONECT    7    3                                                            
CONECT    8    4                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for HMDB0255101 (N-Chlorosuccinimide)

COMPND    HMDB0255101
HETATM    1  O1  UNL     1       1.076  -2.261   0.068  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.594  -1.114   0.155  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.853  -0.727   0.310  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.887   0.548  -0.505  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.361   1.208  -0.035  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.566   2.434   0.169  1.00  0.00           O  
HETATM    7  N1  UNL     1       1.282   0.137   0.133  1.00  0.00           N  
HETATM    8 CL1  UNL     1       3.005   0.310   0.290  1.00  0.00          CL  
HETATM    9  H1  UNL     1      -1.048  -0.433   1.371  1.00  0.00           H  
HETATM   10  H2  UNL     1      -1.531  -1.498  -0.057  1.00  0.00           H  
HETATM   11  H3  UNL     1      -0.784   0.238  -1.572  1.00  0.00           H  
HETATM   12  H4  UNL     1      -1.782   1.157  -0.327  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7
CONECT    3    4    9   10
CONECT    4    5   11   12
CONECT    5    6    6    7
CONECT    7    8
END
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SMILES for HMDB0255101 (N-Chlorosuccinimide)

ClN1C(=O)CCC1=O
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INCHI for HMDB0255101 (N-Chlorosuccinimide)

InChI=1S/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1-Chloro-2,5-pyrrolidine-dioneChEBI
1-Chloro-2,5-pyrrolidinedioneChEBI
ChlorosuccinimideChEBI
NCSChEBI
SuccinchlorimideChEBI
Succinic N-chloroimideChEBI
SuccinochlorimideChEBI
N-ChlorosuccinimideMeSH
Chemical FormulaC4H4ClNO2
Average Molecular Weight133.53
Monoisotopic Molecular Weight132.9930561
IUPAC Name1-chloropyrrolidine-2,5-dione
Traditional Namechlorosuccinimide
CAS Registry NumberNot Available
SMILES
ClN1C(=O)CCC1=O
InChI Identifier
InChI=1S/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2
InChI KeyJRNVZBWKYDBUCA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolidine-2-ones. These are pyrrolidines which bear a C=O group at position 2 of the pyrrolidine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassPyrrolidones
Direct ParentPyrrolidine-2-ones
Alternative Parents
Substituents
  • 2-pyrrolidone
  • Dicarboximide
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • 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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Chlorosuccinimide
METLIN IDNot Available
PubChem Compound31398
PDB IDNot Available
ChEBI ID53203
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 ]