Jump To Section:

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 00:55:18 UTC

Update Date

2023-02-21 17:29:53 UTC

HMDB ID

HMDB0060345

Secondary Accession Numbers

HMDB60345

Metabolite Identification

Common Name

2-Chloro-5-methyl-cis-dienelactone

Description

2-Chloro-5-methyl-cis-dienelactone belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 2-Chloro-5-methyl-cis-dienelactone 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                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0       2.109  -2.943   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.267  -1.375   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       1.060   3.620   0.000  0.00  0.00          Cl+0
HETATM    9  O   UNK     0       4.893   0.032   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.172  -2.621   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.290  -0.290   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4    5                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2    7    8                                                  
CONECT    5    2    3   12                                                  
CONECT    6    3    9   10                                                  
CONECT    7    4   11   12                                                  
CONECT    8    4                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    5    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₇H₅ClO₄

Average Molecular Weight

188.565

Monoisotopic Molecular Weight

187.987636355

IUPAC Name

2-[(2E)-4-chloro-5-oxo-2,5-dihydrofuran-2-ylidene]propanoic acid

Traditional Name

2-[(2E)-4-chloro-5-oxofuran-2-ylidene]propanoic acid

CAS Registry Number

Not Available

SMILES

C\C(C(O)=O)=C1/OC(=O)C(Cl)=C1

InChI Identifier

InChI=1S/C7H5ClO4/c1-3(6(9)10)5-2-4(8)7(11)12-5/h2H,1H3,(H,9,10)/b5-3+

InChI Key

KPWMDCDICLSMLX-HWKANZROSA-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:81655 )

Ontology

Not Available

Exogenous (HMDB: HMDB0060345)

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	1.99 g/L	ALOGPS
logP	1.24	ALOGPS
logP	0.97	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	2.82	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	42.47 m³·mol⁻¹	ChemAxon
Polarizability	16.15 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]+	141.998	30932474
DeepCCS	[M-H]-	139.64	30932474
DeepCCS	[M-2H]-	173.445	30932474
DeepCCS	[M+Na]+	148.371	30932474
AllCCS	[M+H]+	137.7	32859911
AllCCS	[M+H-H2O]+	133.5	32859911
AllCCS	[M+NH4]+	141.7	32859911
AllCCS	[M+Na]+	142.8	32859911
AllCCS	[M-H]-	132.7	32859911
AllCCS	[M+Na-2H]-	133.7	32859911
AllCCS	[M+HCOO]-	134.9	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 × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.85 minutes	32390414
Predicted by Siyang on May 30, 2022	12.3208 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.85 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1418.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	417.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	88.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	267.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	92.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	361.1 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	457.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	520.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	817.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	290.7 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	1211.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	273.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	366.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	897.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	282.7 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	388.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Chloro-5-methyl-cis-dienelactone	C\C(C(O)=O)=C1/OC(=O)C(Cl)=C1	2656.6	Standard polar	33892256
2-Chloro-5-methyl-cis-dienelactone	C\C(C(O)=O)=C1/OC(=O)C(Cl)=C1	1592.3	Standard non polar	33892256
2-Chloro-5-methyl-cis-dienelactone	C\C(C(O)=O)=C1/OC(=O)C(Cl)=C1	1523.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Chloro-5-methyl-cis-dienelactone,1TMS,isomer #1	C/C(C(=O)O[Si](C)(C)C)=C1/C=C(Cl)C(=O)O1	1690.0	Semi standard non polar	33892256
2-Chloro-5-methyl-cis-dienelactone,1TBDMS,isomer #1	C/C(C(=O)O[Si](C)(C)C(C)(C)C)=C1/C=C(Cl)C(=O)O1	1911.3	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-Chloro-5-methyl-cis-dienelactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9500000000-0c0e917f3f168223429b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Chloro-5-methyl-cis-dienelactone GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9420000000-c2d676d0c98460878ffc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Chloro-5-methyl-cis-dienelactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Chloro-5-methyl-cis-dienelactone 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-Chloro-5-methyl-cis-dienelactone 10V, Positive-QTOF	splash10-00ds-3900000000-6d40a6fa3ed24e74776f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methyl-cis-dienelactone 20V, Positive-QTOF	splash10-00dl-2900000000-92109913104ec0f66f31	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methyl-cis-dienelactone 40V, Positive-QTOF	splash10-0f6t-9300000000-3b8efb5bb1a2cf1e60e8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methyl-cis-dienelactone 10V, Negative-QTOF	splash10-000f-0900000000-03fcef1f1103ddddc8e8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methyl-cis-dienelactone 20V, Negative-QTOF	splash10-0006-0900000000-242d44f55f3ec39ec8d0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methyl-cis-dienelactone 40V, Negative-QTOF	splash10-0005-9300000000-dc4af8cc5fc38c039d3b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methyl-cis-dienelactone 10V, Positive-QTOF	splash10-000l-0900000000-31b9c09765ec3832dbdb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methyl-cis-dienelactone 20V, Positive-QTOF	splash10-0006-0900000000-69b42701dc561aa74ce4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methyl-cis-dienelactone 40V, Positive-QTOF	splash10-0f6y-9700000000-b9706e37616f156cb517	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methyl-cis-dienelactone 10V, Negative-QTOF	splash10-0006-0900000000-01de3b4b68ec8ddb1516	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methyl-cis-dienelactone 20V, Negative-QTOF	splash10-0006-1900000000-ca7f8c2583a32213b6e9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methyl-cis-dienelactone 40V, Negative-QTOF	splash10-03ec-6900000000-8f6c16c50dc95880f13c	2021-10-12	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

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

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

C18304

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9543297

PDB ID

Not Available

ChEBI ID

81655

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-Chloro-5-methyl-cis-dienelactone + Water → 2-Chloro-5-methylmaleylacetate	details

Showing metabocard for 2-Chloro-5-methyl-cis-dienelactone (HMDB0060345)

MOL for HMDB0060345 (2-Chloro-5-methyl-cis-dienelactone)

3D MOL for HMDB0060345 (2-Chloro-5-methyl-cis-dienelactone)

3D SDF for HMDB0060345 (2-Chloro-5-methyl-cis-dienelactone)

3D-SDF for HMDB0060345 (2-Chloro-5-methyl-cis-dienelactone)

PDB for HMDB0060345 (2-Chloro-5-methyl-cis-dienelactone)

3D PDB for HMDB0060345 (2-Chloro-5-methyl-cis-dienelactone)

SMILES for HMDB0060345 (2-Chloro-5-methyl-cis-dienelactone)

INCHI for HMDB0060345 (2-Chloro-5-methyl-cis-dienelactone)

Structure for HMDB0060345 (2-Chloro-5-methyl-cis-dienelactone)

3D Structure for HMDB0060345 (2-Chloro-5-methyl-cis-dienelactone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions