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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 00:56:51 UTC

Update Date

2023-02-21 17:29:55 UTC

HMDB ID

HMDB0060368

Secondary Accession Numbers

HMDB60368

Metabolite Identification

Common Name

3-Chloro-2-methyldienelactone

Description

3-Chloro-2-methyldienelactone belongs to the class of organic compounds known as halogenated fatty acids. These are fatty acids with a chain that carries a halogen atom (Cl,F,I,Br). 3-Chloro-2-methyldienelactone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HEADER    PROTEIN                                 12-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-FEB-20         0                                  
HETATM    1  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0       3.770   1.651   0.000  0.00  0.00          Cl+0
HETATM    5  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.290  -0.290   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.109  -2.943   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.014  -4.188   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.577  -3.104   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-[(2Z)-3-Chloro-4-methyl-5-oxo-2,5-dihydrofuran-2-ylidene]acetate	Generator

Chemical Formula

C₇H₅ClO₄

Average Molecular Weight

188.565

Monoisotopic Molecular Weight

187.987636355

IUPAC Name

2-[(2Z)-3-chloro-4-methyl-5-oxo-2,5-dihydrofuran-2-ylidene]acetic acid

Traditional Name

[(2Z)-3-chloro-4-methyl-5-oxofuran-2-ylidene]acetic acid

CAS Registry Number

Not Available

SMILES

CC1=C(Cl)\C(OC1=O)=C\C(O)=O

InChI Identifier

InChI=1S/C7H5ClO4/c1-3-6(8)4(2-5(9)10)12-7(3)11/h2H,1H3,(H,9,10)/b4-2-

InChI Key

OYEYSZZDZDSDCR-RQOWECAXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as halogenated fatty acids. These are fatty acids with a chain that carries a halogen atom (Cl,F,I,Br).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Halogenated fatty acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

halo fatty acid (CHEBI:81660 )

Ontology

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	2.1 g/L	ALOGPS
logP	1.31	ALOGPS
logP	0.82	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	2.91	ChemAxon
pKa (Strongest Basic)	-7.1	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	42.4 m³·mol⁻¹	ChemAxon
Polarizability	15.98 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]+	137.204	30932474
DeepCCS	[M-H]-	133.377	30932474
DeepCCS	[M-2H]-	171.01	30932474
DeepCCS	[M+Na]+	146.549	30932474
AllCCS	[M+H]+	137.8	32859911
AllCCS	[M+H-H2O]+	133.6	32859911
AllCCS	[M+NH4]+	141.8	32859911
AllCCS	[M+Na]+	142.9	32859911
AllCCS	[M-H]-	132.8	32859911
AllCCS	[M+Na-2H]-	133.8	32859911
AllCCS	[M+HCOO]-	135.1	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.	6.07 minutes	32390414
Predicted by Siyang on May 30, 2022	13.4624 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.93 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1561.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	459.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	113.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	303.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	100.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	398.4 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	558.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	577.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	908.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	341.2 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	1353.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	315.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	405.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	951.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	324.7 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	422.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Chloro-2-methyldienelactone	CC1=C(Cl)\C(OC1=O)=C\C(O)=O	2637.6	Standard polar	33892256
3-Chloro-2-methyldienelactone	CC1=C(Cl)\C(OC1=O)=C\C(O)=O	1571.1	Standard non polar	33892256
3-Chloro-2-methyldienelactone	CC1=C(Cl)\C(OC1=O)=C\C(O)=O	1597.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Chloro-2-methyldienelactone,1TMS,isomer #1	CC1=C(Cl)/C(=C/C(=O)O[Si](C)(C)C)OC1=O	1645.1	Semi standard non polar	33892256
3-Chloro-2-methyldienelactone,1TBDMS,isomer #1	CC1=C(Cl)/C(=C/C(=O)O[Si](C)(C)C(C)(C)C)OC1=O	1870.6	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 - 3-Chloro-2-methyldienelactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00b9-9300000000-c56f663dc97fbf7b23d4	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chloro-2-methyldienelactone GC-MS (1 TMS) - 70eV, Positive	splash10-00b9-9210000000-1e1308d70ec5ed6b8b3e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Chloro-2-methyldienelactone 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-Chloro-2-methyldienelactone 10V, Positive-QTOF	splash10-00di-0900000000-386650005cde9de0fb58	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-2-methyldienelactone 20V, Positive-QTOF	splash10-00dl-0900000000-568e59ba2cdfa2e8aee9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-2-methyldienelactone 40V, Positive-QTOF	splash10-05fu-9500000000-3b306362272b8169b2a1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-2-methyldienelactone 10V, Negative-QTOF	splash10-000i-0900000000-ec16251265fd4430d44f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-2-methyldienelactone 20V, Negative-QTOF	splash10-0006-1900000000-f6f9f654f2dd8bbd4107	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-2-methyldienelactone 40V, Negative-QTOF	splash10-014l-4900000000-0f2784bd9df3eae0fb22	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-2-methyldienelactone 10V, Positive-QTOF	splash10-0079-0900000000-e544480efe16ddb16583	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-2-methyldienelactone 20V, Positive-QTOF	splash10-0fki-3900000000-9c52988a69ce0c4b0f91	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-2-methyldienelactone 40V, Positive-QTOF	splash10-00kf-9100000000-b174e30b0bb630e8a13b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-2-methyldienelactone 10V, Negative-QTOF	splash10-0006-0900000000-13a59f6e33268d8552fb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-2-methyldienelactone 20V, Negative-QTOF	splash10-0006-0900000000-deb326d52039c1fee17f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Chloro-2-methyldienelactone 40V, Negative-QTOF	splash10-0002-9200000000-fa528d37c181795e6eb4	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

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

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

C18309

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

49787040

PDB ID

Not Available

ChEBI ID

81660

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 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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

3-Chloro-2-methyldienelactone + Water → 3-Chloro-2-methylmaleylacetate	details

Showing metabocard for 3-Chloro-2-methyldienelactone (HMDB0060368)

MOL for HMDB0060368 (3-Chloro-2-methyldienelactone)

3D MOL for HMDB0060368 (3-Chloro-2-methyldienelactone)

3D SDF for HMDB0060368 (3-Chloro-2-methyldienelactone)

3D-SDF for HMDB0060368 (3-Chloro-2-methyldienelactone)

PDB for HMDB0060368 (3-Chloro-2-methyldienelactone)

3D PDB for HMDB0060368 (3-Chloro-2-methyldienelactone)

SMILES for HMDB0060368 (3-Chloro-2-methyldienelactone)

INCHI for HMDB0060368 (3-Chloro-2-methyldienelactone)

Structure for HMDB0060368 (3-Chloro-2-methyldienelactone)

3D Structure for HMDB0060368 (3-Chloro-2-methyldienelactone)

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