ContaminantDB: Dichloromaleimide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 22:10:19 UTC

Update Date

2016-11-09 01:18:01 UTC

Accession Number

CHEM025145

Identification

Common Name

Dichloromaleimide

Class

Small Molecule

Description

Bacterial mutagen produced by chlorination of simulated poultry chiller wate

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4-Dichloro-1H-pyrrole-2,5-dione	HMDB
alpha, beta-Dichloromaleimide	HMDB
Dichloro-maleimide	HMDB
Dichloromaleinimide	HMDB

Chemical Formula

C₄HCl₂NO₂

Average Molecular Mass

165.962 g/mol

Monoisotopic Mass

164.938 g/mol

CAS Registry Number

1193-54-0

IUPAC Name

3,4-dichloro-5-hydroxy-2H-pyrrol-2-one

Traditional Name

3,4-dichloro-5-hydroxypyrrol-2-one

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

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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Nitrogen mustard compounds

Direct Parent

Nitrogen 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.14 g/L	ALOGPS
logP	0.94	ALOGPS
logP	0.51	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.66 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	33.26 m³·mol⁻¹	ChemAxon
Polarizability	12.43 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-044l-5900000000-e975b752f1ab48863c4d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9370000000-64a611a11fba05de59b4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-0f7c59b4c9adaf008578	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-1fb3d6312c50c4377087	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9400000000-13aed952f3a2369d56d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-5821571c71986cf12c52	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-5821571c71986cf12c52	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03xr-7900000000-d583e5d3f4b99e2bb6f7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-9623ea68367db08a6da7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-9623ea68367db08a6da7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9200000000-36d1608933bec6e261df	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-ef1da2b7c4781d53f328	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-ef1da2b7c4781d53f328	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-7f785f25ab353cffaa62	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0031151

FooDB ID

FDB003164

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

13857

ChEBI ID

Not Available

PubChem Compound ID

14513

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

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.

2. Kazmierczak F: Circular dichroism of some optically active 2,3-dichloromaleimides. Enantiomer. 2001;6(4):251-8.

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.

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.

5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Dichloromaleimide (CHEM025145)

Structure for CHEM025145: Dichloromaleimide