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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:49:30 UTC

Update Date

2023-02-21 17:24:28 UTC

HMDB ID

HMDB0034895

Secondary Accession Numbers

HMDB34895

Metabolite Identification

Common Name

3-(Dichloromethylene)-2,5-pyrrolidinedione

Description

3-(Dichloromethylene)-2,5-pyrrolidinedione 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-(Dichloromethylene)-2,5-pyrrolidinedione.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₅H₃Cl₂NO₂

Average Molecular Weight

179.989

Monoisotopic Molecular Weight

178.954083759

IUPAC Name

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

Traditional Name

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

CAS Registry Number

170660-62-5

SMILES

ClC(Cl)=C1CC(=O)NC1=O

InChI Identifier

InChI=1S/C5H3Cl2NO2/c6-4(7)2-1-3(9)8-5(2)10/h1H2,(H,8,9,10)

InChI Key

SKOPRFQCOBOZFB-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
Haloalkene
Azacycle
Vinyl halide
Vinyl chloride
Chloroalkene
Carboxylic acid derivative
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034895)
Cytoplasm (HMDB: HMDB0034895)

Source

Exogenous

Exogenous (HMDB: HMDB0034895)

Food

Food (HMDB: HMDB0034895)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034895)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	192 - 192.5 °C	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	3.15 g/L	ALOGPS
logP	0.78	ALOGPS
logP	0.21	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	8.57	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.17 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	47.06 m³·mol⁻¹	ChemAxon
Polarizability	14.21 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]+	123.929	30932474
DeepCCS	[M-H]-	120.094	30932474
DeepCCS	[M-2H]-	156.822	30932474
DeepCCS	[M+Na]+	132.486	30932474
AllCCS	[M+H]+	135.0	32859911
AllCCS	[M+H-H2O]+	130.7	32859911
AllCCS	[M+NH4]+	139.0	32859911
AllCCS	[M+Na]+	140.2	32859911
AllCCS	[M-H]-	129.5	32859911
AllCCS	[M+Na-2H]-	131.2	32859911
AllCCS	[M+HCOO]-	133.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(Dichloromethylene)-2,5-pyrrolidinedione	ClC(Cl)=C1CC(=O)NC1=O	2631.8	Standard polar	33892256
3-(Dichloromethylene)-2,5-pyrrolidinedione	ClC(Cl)=C1CC(=O)NC1=O	1433.8	Standard non polar	33892256
3-(Dichloromethylene)-2,5-pyrrolidinedione	ClC(Cl)=C1CC(=O)NC1=O	1426.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-(Dichloromethylene)-2,5-pyrrolidinedione,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CC(=C(Cl)Cl)C1=O	1641.1	Semi standard non polar	33892256
3-(Dichloromethylene)-2,5-pyrrolidinedione,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CC(=C(Cl)Cl)C1=O	1558.4	Standard non polar	33892256
3-(Dichloromethylene)-2,5-pyrrolidinedione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CC(=C(Cl)Cl)C1=O	1858.8	Semi standard non polar	33892256
3-(Dichloromethylene)-2,5-pyrrolidinedione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CC(=C(Cl)Cl)C1=O	1806.5	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-(Dichloromethylene)-2,5-pyrrolidinedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a7u-4900000000-f64d8b139784bfe868e3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(Dichloromethylene)-2,5-pyrrolidinedione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(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-(Dichloromethylene)-2,5-pyrrolidinedione 10V, Positive-QTOF	splash10-004i-0900000000-cfa13855b4ae17cdbf6f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(Dichloromethylene)-2,5-pyrrolidinedione 20V, Positive-QTOF	splash10-004i-0900000000-eff69534c27554daa1aa	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(Dichloromethylene)-2,5-pyrrolidinedione 40V, Positive-QTOF	splash10-056r-3900000000-90dfdfb309d9132ae94d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(Dichloromethylene)-2,5-pyrrolidinedione 10V, Negative-QTOF	splash10-004i-0900000000-bbf78cb97bb839cfc2af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(Dichloromethylene)-2,5-pyrrolidinedione 20V, Negative-QTOF	splash10-0a4i-0900000000-69feb8a6afe721e7643f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(Dichloromethylene)-2,5-pyrrolidinedione 40V, Negative-QTOF	splash10-004l-7900000000-1cf003b720adb9e33a81	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(Dichloromethylene)-2,5-pyrrolidinedione 10V, Negative-QTOF	splash10-004i-0900000000-967219844748bec5e62c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(Dichloromethylene)-2,5-pyrrolidinedione 20V, Negative-QTOF	splash10-004i-1900000000-b3ee7f23530f0b8728dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(Dichloromethylene)-2,5-pyrrolidinedione 40V, Negative-QTOF	splash10-0006-9000000000-90726b17dc36e29c5299	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(Dichloromethylene)-2,5-pyrrolidinedione 10V, Positive-QTOF	splash10-004i-0900000000-b83745cdda650fba0d34	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(Dichloromethylene)-2,5-pyrrolidinedione 20V, Positive-QTOF	splash10-004i-1900000000-aa2e9496f6cfd80199af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(Dichloromethylene)-2,5-pyrrolidinedione 40V, Positive-QTOF	splash10-05fr-9300000000-691227f80ff49c7ed5ac	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX 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

FDB013471

KNApSAcK ID

Not Available

Chemspider ID

136392

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

154811

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-(Dichloromethylene)-2,5-pyrrolidinedione (HMDB0034895)

MOL for HMDB0034895 (3-(Dichloromethylene)-2,5-pyrrolidinedione)

3D MOL for HMDB0034895 (3-(Dichloromethylene)-2,5-pyrrolidinedione)

3D SDF for HMDB0034895 (3-(Dichloromethylene)-2,5-pyrrolidinedione)

3D-SDF for HMDB0034895 (3-(Dichloromethylene)-2,5-pyrrolidinedione)

PDB for HMDB0034895 (3-(Dichloromethylene)-2,5-pyrrolidinedione)

3D PDB for HMDB0034895 (3-(Dichloromethylene)-2,5-pyrrolidinedione)

SMILES for HMDB0034895 (3-(Dichloromethylene)-2,5-pyrrolidinedione)

INCHI for HMDB0034895 (3-(Dichloromethylene)-2,5-pyrrolidinedione)

Structure for HMDB0034895 (3-(Dichloromethylene)-2,5-pyrrolidinedione)

3D Structure for HMDB0034895 (3-(Dichloromethylene)-2,5-pyrrolidinedione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra