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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 00:56:34 UTC

Update Date

2022-03-07 03:17:44 UTC

HMDB ID

HMDB0060364

Secondary Accession Numbers

HMDB60364

Metabolite Identification

Common Name

2,5-Dichloro-carboxymethylenebut-2-en-4-olide

Description

2,5-Dichloro-carboxymethylenebut-2-en-4-olide belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 2,5-Dichloro-carboxymethylenebut-2-en-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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       2.735  -1.536   0.000  0.00  0.00          Cl+0
HETATM    8 Cl   UNK     0       2.393   4.390   0.000  0.00  0.00          Cl+0
HETATM    9  O   UNK     0      -1.608   3.620   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.274   5.930   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6    7                                                  
CONECT    3    1    4   12                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    9   10                                                  
CONECT    6    2   11   12                                                  
CONECT    7    2                                                            
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    3    6                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₆H₂Cl₂O₄

Average Molecular Weight

208.984

Monoisotopic Molecular Weight

207.933013966

IUPAC Name

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

Traditional Name

chloro(4-chloro-5-oxofuran-2-ylidene)acetic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H2Cl2O4/c7-2-1-3(12-6(2)11)4(8)5(9)10/h1H,(H,9,10)

InChI Key

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0060364)

Process

Not Available

Role

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	0.78 g/L	ALOGPS
logP	1.65	ALOGPS
logP	0.96	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	2.02	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	42.91 m³·mol⁻¹	ChemAxon
Polarizability	16.12 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]+	135.464	30932474
DeepCCS	[M-H]-	132.838	30932474
DeepCCS	[M-2H]-	168.737	30932474
DeepCCS	[M+Na]+	143.765	30932474
AllCCS	[M+H]+	140.4	32859911
AllCCS	[M+H-H2O]+	136.2	32859911
AllCCS	[M+NH4]+	144.2	32859911
AllCCS	[M+Na]+	145.3	32859911
AllCCS	[M-H]-	132.8	32859911
AllCCS	[M+Na-2H]-	133.8	32859911
AllCCS	[M+HCOO]-	135.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	5.49 minutes	32390414
Predicted by Siyang on May 30, 2022	12.9136 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.23 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1471.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	460.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	114.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	319.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	143.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	379.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	549.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	774.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	870.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	277.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1310.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	311.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	389.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	1006.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	311.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	444.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,5-Dichloro-carboxymethylenebut-2-en-4-olide	OC(=O)C(Cl)=C1OC(=O)C(Cl)=C1	2622.6	Standard polar	33892256
2,5-Dichloro-carboxymethylenebut-2-en-4-olide	OC(=O)C(Cl)=C1OC(=O)C(Cl)=C1	1727.4	Standard non polar	33892256
2,5-Dichloro-carboxymethylenebut-2-en-4-olide	OC(=O)C(Cl)=C1OC(=O)C(Cl)=C1	1615.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,5-Dichloro-carboxymethylenebut-2-en-4-olide,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(Cl)=C1C=C(Cl)C(=O)O1	1756.3	Semi standard non polar	33892256
2,5-Dichloro-carboxymethylenebut-2-en-4-olide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(Cl)=C1C=C(Cl)C(=O)O1	1985.4	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 - 2,5-Dichloro-carboxymethylenebut-2-en-4-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bt9-9410000000-938b7a1eabe28aa7bf3e	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dichloro-carboxymethylenebut-2-en-4-olide GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9340000000-e2f6e4ae5c69b66e26b9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dichloro-carboxymethylenebut-2-en-4-olide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dichloro-carboxymethylenebut-2-en-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 - 2,5-Dichloro-carboxymethylenebut-2-en-4-olide 10V, Positive-QTOF	splash10-0a4i-0190000000-4712b8b94c4f8a43c8c8	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dichloro-carboxymethylenebut-2-en-4-olide 20V, Positive-QTOF	splash10-0a4i-0190000000-8dc24320b28d57a07858	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dichloro-carboxymethylenebut-2-en-4-olide 40V, Positive-QTOF	splash10-03xr-1900000000-84e21f0eb8cd6da40ed9	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dichloro-carboxymethylenebut-2-en-4-olide 10V, Negative-QTOF	splash10-08fr-0960000000-59de228302d9f44d8110	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dichloro-carboxymethylenebut-2-en-4-olide 20V, Negative-QTOF	splash10-08fr-0960000000-d9abd16770a3305f05ff	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dichloro-carboxymethylenebut-2-en-4-olide 40V, Negative-QTOF	splash10-02t9-1900000000-1c1114cf81cf1fd6cb6a	2015-09-15	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	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

443961

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

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

2,5-Dichloro-carboxymethylenebut-2-en-4-olide + Water → 2,5-Dichloro-4-oxohex-2-enedioate	details

Showing metabocard for 2,5-Dichloro-carboxymethylenebut-2-en-4-olide (HMDB0060364)

MOL for HMDB0060364 (2,5-Dichloro-carboxymethylenebut-2-en-4-olide)

3D MOL for HMDB0060364 (2,5-Dichloro-carboxymethylenebut-2-en-4-olide)

3D SDF for HMDB0060364 (2,5-Dichloro-carboxymethylenebut-2-en-4-olide)

3D-SDF for HMDB0060364 (2,5-Dichloro-carboxymethylenebut-2-en-4-olide)

PDB for HMDB0060364 (2,5-Dichloro-carboxymethylenebut-2-en-4-olide)

3D PDB for HMDB0060364 (2,5-Dichloro-carboxymethylenebut-2-en-4-olide)

SMILES for HMDB0060364 (2,5-Dichloro-carboxymethylenebut-2-en-4-olide)

INCHI for HMDB0060364 (2,5-Dichloro-carboxymethylenebut-2-en-4-olide)

Structure for HMDB0060364 (2,5-Dichloro-carboxymethylenebut-2-en-4-olide)

3D Structure for HMDB0060364 (2,5-Dichloro-carboxymethylenebut-2-en-4-olide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions