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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:19 UTC
Update Date2019-07-23 06:08:08 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. Dichloromaleimide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862088
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
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point175 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.14 g/LALOGPS
logP0.94ALOGPS
logP0.51ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.66 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.26 m³·mol⁻¹ChemAxon
Polarizability12.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-044l-5900000000-e975b752f1ab48863c4dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9370000000-64a611a11fba05de59b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-0f7c59b4c9adaf008578Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-1fb3d6312c50c4377087Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9400000000-13aed952f3a2369d56d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-5821571c71986cf12c52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-5821571c71986cf12c52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xr-7900000000-d583e5d3f4b99e2bb6f7Spectrum
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
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.. .