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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:49:39 UTC

Update Date

2022-03-07 02:54:16 UTC

HMDB ID

HMDB0034898

Secondary Accession Numbers

HMDB34898

Metabolite Identification

Common Name

3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione

Description

3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione, also known as DC-DCM-p, 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. Based on a literature review very few articles have been published on 3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.521  -0.141   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.018  -0.141   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.496  -1.606   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -0.251  -2.512   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       0.990  -1.606   0.000  0.00  0.00           C+0
HETATM    6 Cl   UNK     0      -1.416   1.347   0.000  0.00  0.00          Cl+0
HETATM    7 Cl   UNK     0      -2.506  -0.539   0.000  0.00  0.00          Cl+0
HETATM    8  C   UNK     0       1.429   1.103   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0       0.806   2.512   0.000  0.00  0.00          Cl+0
HETATM   10 Cl   UNK     0       2.961   0.939   0.000  0.00  0.00          Cl+0
HETATM   11  O   UNK     0       2.453  -2.083   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.961  -2.081   0.000  0.00  0.00           O+0
CONECT    1    2    5    8                                                  
CONECT    2    1    3    6    7                                             
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    1    4   11                                                  
CONECT    6    2                                                            
CONECT    7    2                                                            
CONECT    8    1    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5                                                            
CONECT   12    3                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
DC-DCM-p	HMDB
3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione	MeSH

Chemical Formula

C₅HCl₄NO₂

Average Molecular Weight

248.879

Monoisotopic Molecular Weight

246.876139109

IUPAC Name

3,3-dichloro-4-(dichloromethylidene)pyrrolidine-2,5-dione

Traditional Name

3,3-dichloro-4-(dichloromethylidene)pyrrolidine-2,5-dione

CAS Registry Number

165606-93-9

SMILES

ClC(Cl)=C1C(=O)NC(=O)C1(Cl)Cl

InChI Identifier

InChI=1S/C5HCl4NO2/c6-2(7)1-3(11)10-4(12)5(1,8)9/h(H,10,11,12)

InChI Key

QURBORJOJALFAD-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

Pyrrolidones

Direct Parent

Pyrrolidine-2-ones

Alternative Parents

Substituents

2-pyrrolidone
Carboxylic acid imide
Dicarboximide
Carboxylic acid imide, n-unsubstituted
Vinylogous halide
Ketene acetal or derivatives
Lactam
Carboxylic acid derivative
Azacycle
Vinyl chloride
Vinyl halide
Chloroalkene
Haloalkene
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Alkyl chloride
Alkyl halide
Carbonyl group
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034898)
Cytoplasm (HMDB: HMDB0034898)

Source

Exogenous

Food

Food (HMDB: HMDB0034898)

Not Available

Nutrient (HMDB: HMDB0034898)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.031 g/L	ALOGPS
logP	2.2	ALOGPS
logP	1.85	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	5.3	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.17 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	57.01 m³·mol⁻¹	ChemAxon
Polarizability	18.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	141.624	30932474
DeepCCS	[M-H]-	139.266	30932474
DeepCCS	[M-2H]-	174.288	30932474
DeepCCS	[M+Na]+	149.148	30932474
AllCCS	[M+H]+	144.0	32859911
AllCCS	[M+H-H2O]+	140.2	32859911
AllCCS	[M+NH4]+	147.4	32859911
AllCCS	[M+Na]+	148.4	32859911
AllCCS	[M-H]-	137.0	32859911
AllCCS	[M+Na-2H]-	138.2	32859911
AllCCS	[M+HCOO]-	139.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione	ClC(Cl)=C1C(=O)NC(=O)C1(Cl)Cl	2712.4	Standard polar	33892256
3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione	ClC(Cl)=C1C(=O)NC(=O)C1(Cl)Cl	1673.3	Standard non polar	33892256
3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione	ClC(Cl)=C1C(=O)NC(=O)C1(Cl)Cl	1449.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione,1TMS,isomer #1	C[Si](C)(C)N1C(=O)C(=C(Cl)Cl)C(Cl)(Cl)C1=O	1773.8	Semi standard non polar	33892256
3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione,1TMS,isomer #1	C[Si](C)(C)N1C(=O)C(=C(Cl)Cl)C(Cl)(Cl)C1=O	1661.7	Standard non polar	33892256
3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C(=C(Cl)Cl)C(Cl)(Cl)C1=O	1986.2	Semi standard non polar	33892256
3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C(=C(Cl)Cl)C(Cl)(Cl)C1=O	1885.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fdk-2590000000-7bc6b1e84ce985249822	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione 10V, Positive-QTOF	splash10-0002-0090000000-b07712e42c9838fcacae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione 20V, Positive-QTOF	splash10-0002-0190000000-bed612eb59897d200719	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione 40V, Positive-QTOF	splash10-004i-0910000000-76c04cad403cc7682a0b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione 10V, Negative-QTOF	splash10-0002-0090000000-7581e642ce21fd8a61e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione 20V, Negative-QTOF	splash10-0002-0090000000-7581e642ce21fd8a61e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione 40V, Negative-QTOF	splash10-00kb-6090000000-a5a85e4efb0bf6011603	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione 10V, Negative-QTOF	splash10-0002-0090000000-80e2b987519141a3ba2b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione 20V, Negative-QTOF	splash10-0002-0090000000-80e2b987519141a3ba2b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione 40V, Negative-QTOF	splash10-0007-9050000000-5880ca14ac5a922e9277	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione 10V, Positive-QTOF	splash10-0002-0090000000-29ebdae4eb810595cdae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione 20V, Positive-QTOF	splash10-0002-0090000000-29ebdae4eb810595cdae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione 40V, Positive-QTOF	splash10-03di-0590000000-08625fae66014bb5018f	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013475

KNApSAcK ID

Not Available

Chemspider ID

136381

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

154800

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione (HMDB0034898)

MOL for HMDB0034898 (3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione)

3D MOL for HMDB0034898 (3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione)

3D SDF for HMDB0034898 (3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione)

3D-SDF for HMDB0034898 (3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione)

PDB for HMDB0034898 (3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione)

3D PDB for HMDB0034898 (3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione)

SMILES for HMDB0034898 (3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione)

INCHI for HMDB0034898 (3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione)

Structure for HMDB0034898 (3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione)

3D Structure for HMDB0034898 (3,3-Dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra