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Showing metabocard for Dichloromaleimide (HMDB0031151)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:19 UTC
Update Date2023-02-21 17:19:54 UTC
HMDB IDHMDB0031151
Secondary Accession Numbers
  • HMDB31151
Metabolite Identification
Common NameDichloromaleimide
DescriptionDichloromaleimide belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom. Based on a literature review a small amount of articles have been published on Dichloromaleimide.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031151 (Dichloromaleimide)

  Mrv0541 05061305462D          

  9  9  0  0  0  0            999 V2000
    1.2352    0.6294    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
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    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  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
M  END
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3D MOL for HMDB0031151 (Dichloromaleimide)

HMDB0031151
     RDKit          3D
Dichloromaleimide
 10 10  0  0  0  0  0  0  0  0999 V2000
   -2.3552   -1.5432   -0.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2478   -0.9058   -0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0619   -1.4290   -0.1051 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9087   -0.4652   -0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3219   -0.5950   -0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1606    0.7782   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8691    2.3761   -0.0739 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1217    0.5439   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575    1.7069   -0.0169 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8599   -0.4669    0.7141 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
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8  2  1  0
  5 10  1  0
M  END
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3D SDF for HMDB0031151 (Dichloromaleimide)

  Mrv0541 05061305462D          

  9  9  0  0  0  0            999 V2000
    1.2352    0.6294    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
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    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  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031151

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=NC(=O)C(Cl)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C4HCl2NO2/c5-1-2(6)4(9)7-3(1)8/h(H,7,8,9)

> <INCHI_KEY>
KVBAKSQRUXXHCK-UHFFFAOYSA-N

> <FORMULA>
C4HCl2NO2

> <MOLECULAR_WEIGHT>
165.962

> <EXACT_MASS>
164.938433695

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
12.429126905722796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4-dichloro-5-hydroxy-2H-pyrrol-2-one

> <ALOGPS_LOGP>
0.94

> <JCHEM_LOGP>
0.5095025126666668

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.223344958862329

> <JCHEM_PKA_STRONGEST_BASIC>
-6.568545671803873

> <JCHEM_POLAR_SURFACE_AREA>
49.660000000000004

> <JCHEM_REFRACTIVITY>
33.2557

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dichloro-5-hydroxypyrrol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0031151 (Dichloromaleimide)

HMDB0031151
     RDKit          3D
Dichloromaleimide
 10 10  0  0  0  0  0  0  0  0999 V2000
   -2.3552   -1.5432   -0.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2478   -0.9058   -0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0619   -1.4290   -0.1051 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9087   -0.4652   -0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3219   -0.5950   -0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1606    0.7782   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8691    2.3761   -0.0739 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1217    0.5439   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575    1.7069   -0.0169 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8599   -0.4669    0.7141 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
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8  2  1  0
  5 10  1  0
M  END
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PDB for HMDB0031151 (Dichloromaleimide)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    5 Cl   UNK     0       3.770   1.651   0.000  0.00  0.00          Cl+0
HETATM    6 Cl   UNK     0       1.060   3.620   0.000  0.00  0.00          Cl+0
HETATM    7  N   UNK     0       0.290  -0.290   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
CONECT    1    2    3    5                                                  
CONECT    2    1    4    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    2    7    9                                                  
CONECT    5    1                                                            
CONECT    6    2                                                            
CONECT    7    3    4                                                       
CONECT    8    3                                                            
CONECT    9    4                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for HMDB0031151 (Dichloromaleimide)

COMPND    HMDB0031151
HETATM    1  O1  UNL     1      -2.355  -1.543  -0.059  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.248  -0.906  -0.073  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.062  -1.429  -0.105  1.00  0.00           N  
HETATM    4  C2  UNL     1       0.909  -0.465  -0.110  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.322  -0.595  -0.139  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.161   0.778  -0.080  1.00  0.00           C  
HETATM    7 CL1  UNL     1       0.869   2.376  -0.074  1.00  0.00          CL  
HETATM    8  C4  UNL     1      -1.122   0.544  -0.057  1.00  0.00           C  
HETATM    9 CL2  UNL     1      -2.457   1.707  -0.017  1.00  0.00          CL  
HETATM   10  H1  UNL     1       2.860  -0.467   0.714  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    8
CONECT    3    4    4
CONECT    4    5    6
CONECT    5   10
CONECT    6    7    8    8
CONECT    8    9
END
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SMILES for HMDB0031151 (Dichloromaleimide)

OC1=NC(=O)C(Cl)=C1Cl
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INCHI for HMDB0031151 (Dichloromaleimide)

InChI=1S/C4HCl2NO2/c5-1-2(6)4(9)7-3(1)8/h(H,7,8,9)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
3,4-Dichloro-1H-pyrrole-2,5-dioneHMDB
alpha, beta-DichloromaleimideHMDB
Dichloro-maleimideHMDB
DichloromaleinimideHMDB
Chemical FormulaC4HCl2NO2
Average Molecular Weight165.962
Monoisotopic Molecular Weight164.938433695
IUPAC Name3,4-dichloro-5-hydroxy-2H-pyrrol-2-one
Traditional Name3,4-dichloro-5-hydroxypyrrol-2-one
CAS Registry Number1193-54-0
SMILES
OC1=NC(=O)C(Cl)=C1Cl
InChI Identifier
InChI=1S/C4HCl2NO2/c5-1-2(6)4(9)7-3(1)8/h(H,7,8,9)
InChI KeyKVBAKSQRUXXHCK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassNitrogen mustard compounds
Direct ParentNitrogen mustard compounds
Alternative Parents
Substituents
  • Nitrogen mustard
  • Maleimide
  • Carboxylic acid imide
  • Dicarboximide
  • Carboxylic acid imide, n-unsubstituted
  • Pyrroline
  • Vinylogous halide
  • Carboxylic acid derivative
  • Azacycle
  • Vinyl chloride
  • Vinyl halide
  • Chloroalkene
  • Haloalkene
  • Organoheterocyclic compound
  • Organochloride
  • Organohalogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point175 °CNot 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 Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003164
KNApSAcK IDNot Available
Chemspider ID13857
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14513
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. Quintao NL, da Silva GF, Antonialli CS, de Campos-Buzzi F, Correa R, Filho VC: N-antipyrine-3, 4-dichloromaleimide, an effective cyclic imide for the treatment of chronic pain: the role of the glutamatergic system. Anesth Analg. 2010 Mar 1;110(3):942-50. doi: 10.1213/ANE.0b013e3181cbd7f6. [PubMed:20185671 ]
  2. Kazmierczak F: Circular dichroism of some optically active 2,3-dichloromaleimides. Enantiomer. 2001;6(4):251-8. [PubMed:11693488 ]
  3. de Campos F, Correa R, de Souza MM, Yunes RA, Nunes RJ, Cechinel-Filho V: Studies on new cyclic imides obtained from aminophenazone with analgesic properties. Potent effects of a 3,4-dichloromaleimide derivative. Arzneimittelforschung. 2002;52(6):455-61. [PubMed:12109046 ]
  4. Lopez SN, Castelli MV, de Campos F, Correa R, Cechinel Filho V, Yunes RA, Zamora MA, Enriz RD, Ribas JC, Furlan RL, Zacchino SA: In vitro antifungal properties structure-activity relationships and studies on the mode of action of N-phenyl, N-aryl, N-phenylalkyl maleimides and related compounds. Arzneimittelforschung. 2005;55(2):123-32. [PubMed:15787280 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .