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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:22:03 UTC

Update Date

2022-03-07 03:17:45 UTC

HMDB ID

HMDB0060455

Secondary Accession Numbers

HMDB60455

Metabolite Identification

Common Name

cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide

Description

cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide is an extremely weak basic (essentially neutral) compound (based on its pKa). These are dihydrofurans with a carbonyk group at the C2 carbon atom.

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

C₆H₃ClO₄

Average Molecular Weight

174.539

Monoisotopic Molecular Weight

173.971986291

IUPAC Name

2-(4-chloro-5-oxo-2,5-dihydrofuran-2-ylidene)acetic acid

Traditional Name

C6H3ClO4

CAS Registry Number

Not Available

SMILES

OC(=O)C=C1OC(=O)C(Cl)=C1

InChI Identifier

InChI=1S/C6H3ClO4/c7-4-1-3(2-5(8)9)11-6(4)10/h1-2H,(H,8,9)

InChI Key

ADSGHWJRPOXXTD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Dicarboxylic acid or derivatives
Enol ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Chloroalkene
Vinyl chloride
Vinyl halide
Haloalkene
Carbonyl group
Organohalogen compound
Organochloride
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

butenolide (CHEBI:38122 )

Ontology

Not Available

Not Available

Not Available

Not Available

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	5.77 g/L	ALOGPS
logP	1.05	ALOGPS
logP	0.57	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	2.68	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	38.12 m³·mol⁻¹	ChemAxon
Polarizability	14.13 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]+	134.4	30932474
DeepCCS	[M-H]-	130.708	30932474
DeepCCS	[M-2H]-	168.485	30932474
DeepCCS	[M+Na]+	144.024	30932474
AllCCS	[M+H]+	134.8	32859911
AllCCS	[M+H-H2O]+	130.4	32859911
AllCCS	[M+NH4]+	138.9	32859911
AllCCS	[M+Na]+	140.1	32859911
AllCCS	[M-H]-	128.3	32859911
AllCCS	[M+Na-2H]-	129.6	32859911
AllCCS	[M+HCOO]-	131.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide	OC(=O)C=C1OC(=O)C(Cl)=C1	2630.5	Standard polar	33892256
cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide	OC(=O)C=C1OC(=O)C(Cl)=C1	1597.2	Standard non polar	33892256
cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide	OC(=O)C=C1OC(=O)C(Cl)=C1	1464.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide,1TMS,isomer #1	C[Si](C)(C)OC(=O)C=C1C=C(Cl)C(=O)O1	1620.5	Semi standard non polar	33892256
cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C=C1C=C(Cl)C(=O)O1	1850.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9600000000-28d9b0ae00663dfea334	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-7920000000-83ab59823f2fb33276f7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide 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 - cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide 10V, Positive-QTOF	splash10-0a4i-0900000000-d61e2e64214d5b0cd72c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide 20V, Positive-QTOF	splash10-0a4i-0900000000-fded875ec2eed03ad1cb	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide 40V, Positive-QTOF	splash10-03e9-6900000000-c59605f18e643e6d4338	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide 10V, Negative-QTOF	splash10-00b9-1900000000-4a9ed54244b4e3b06f6d	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide 20V, Negative-QTOF	splash10-0fi0-0900000000-54827040ae690771727c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide 40V, Negative-QTOF	splash10-0059-7900000000-0fbe0abedbd1cf4d35b6	2015-09-15	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

190225

PDB ID

Not Available

ChEBI ID

38122

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

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Carboxymethylenebutenolidase homolog

General function:: Involved in hydrolase activity
Specific function:: Cysteine hydrolase. Can convert the prodrug olmesartan medoxomil into its pharmacologically active metabolite olmerstatan, an angiotensin receptor blocker, in liver and intestine. May also activate beta-lactam antibiotics faropenem medoxomil and lenampicillin.
Gene Name:: CMBL
Uniprot ID:: Q96DG6
Molecular weight:: Not Available

Reactions

cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide + Water → 2-Chloromaleylacetate	details

Showing metabocard for cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide (HMDB0060455)

MOL for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

3D MOL for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

3D SDF for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

3D-SDF for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

PDB for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

3D PDB for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

SMILES for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

INCHI for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

Structure for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

3D Structure for HMDB0060455 (cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions