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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 01:26:38 UTC

Update Date

2022-03-07 03:17:46 UTC

HMDB ID

HMDB0060518

Secondary Accession Numbers

HMDB60518

Metabolite Identification

Common Name

trans-4-Carboxymethylenebut-2-en-4-olide

Description

trans-4-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. trans-4-Carboxymethylenebut-2-en-4-olide is an extremely weak basic (essentially neutral) compound (based on its pKa). trans-4-Carboxymethylenebut-2-en-4-olide exists in all living organisms, ranging from bacteria to humans. 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

Value	Source
cis-Dienelactone	MeSH
Dienelactone	MeSH
4-Carboxymethylenebut-2-en-4-olide	MeSH

Chemical Formula

C₆H₄O₄

Average Molecular Weight

140.0936

Monoisotopic Molecular Weight

140.010958616

IUPAC Name

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

Traditional Name

(5-oxofuran-2-ylidene)acetic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H4O4/c7-5(8)3-4-1-2-6(9)10-4/h1-3H,(H,7,8)

InChI Key

AYFXPGXAZMFWNH-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
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

butenolide (CHEBI:11972 )

Ontology

Not Available

Exogenous (HMDB: HMDB0060518)

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	23.1 g/L	ALOGPS
logP	0.72	ALOGPS
logP	0.18	ChemAxon
logS	-0.78	ALOGPS
pKa (Strongest Acidic)	3.06	ChemAxon
pKa (Strongest Basic)	-6.9	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	33.33 m³·mol⁻¹	ChemAxon
Polarizability	11.76 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
DarkChem	[M+H]+	131.472	31661259
DarkChem	[M-H]-	125.893	31661259
DeepCCS	[M+H]+	128.73	30932474
DeepCCS	[M-H]-	125.198	30932474
DeepCCS	[M-2H]-	162.638	30932474
DeepCCS	[M+Na]+	138.127	30932474
AllCCS	[M+H]+	128.8	32859911
AllCCS	[M+H-H2O]+	124.2	32859911
AllCCS	[M+NH4]+	133.2	32859911
AllCCS	[M+Na]+	134.4	32859911
AllCCS	[M-H]-	123.4	32859911
AllCCS	[M+Na-2H]-	124.9	32859911
AllCCS	[M+HCOO]-	126.7	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.	3.44 minutes	32390414
Predicted by Siyang on May 30, 2022	11.2585 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.41 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1025.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	412.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	84.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	270.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	99.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	305.0 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	454.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	703.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	742.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	148.4 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	1176.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	273.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	313.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	911.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	278.4 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	368.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
trans-4-Carboxymethylenebut-2-en-4-olide	OC(=O)C=C1OC(=O)C=C1	2560.3	Standard polar	33892256
trans-4-Carboxymethylenebut-2-en-4-olide	OC(=O)C=C1OC(=O)C=C1	1411.8	Standard non polar	33892256
trans-4-Carboxymethylenebut-2-en-4-olide	OC(=O)C=C1OC(=O)C=C1	1396.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
trans-4-Carboxymethylenebut-2-en-4-olide,1TMS,isomer #1	C[Si](C)(C)OC(=O)C=C1C=CC(=O)O1	1556.5	Semi standard non polar	33892256
trans-4-Carboxymethylenebut-2-en-4-olide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C=C1C=CC(=O)O1	1784.8	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 - trans-4-Carboxymethylenebut-2-en-4-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-9100000000-212490d563858022fe2f	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-4-Carboxymethylenebut-2-en-4-olide GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9600000000-40562b3dbdce53cefdb4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-4-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 - trans-4-Carboxymethylenebut-2-en-4-olide 10V, Positive-QTOF	splash10-00di-0900000000-4da24f4d3150d4cb0d9c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-4-Carboxymethylenebut-2-en-4-olide 20V, Positive-QTOF	splash10-00di-2900000000-285620f88db9e73b5ead	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-4-Carboxymethylenebut-2-en-4-olide 40V, Positive-QTOF	splash10-0umi-9300000000-c40d20cf666aab67a491	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-4-Carboxymethylenebut-2-en-4-olide 10V, Negative-QTOF	splash10-000j-5900000000-34a6a177544dbc512389	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-4-Carboxymethylenebut-2-en-4-olide 20V, Negative-QTOF	splash10-0072-9600000000-42a684d27e1e540b3b12	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-4-Carboxymethylenebut-2-en-4-olide 40V, Negative-QTOF	splash10-0f95-9000000000-ff8b053604593c0325bb	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-4-Carboxymethylenebut-2-en-4-olide 10V, Positive-QTOF	splash10-0002-9400000000-32ec3f966c201e73e6b7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-4-Carboxymethylenebut-2-en-4-olide 20V, Positive-QTOF	splash10-0002-9100000000-acf0d7874c4fc167d1fa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-4-Carboxymethylenebut-2-en-4-olide 40V, Positive-QTOF	splash10-0udi-9000000000-f749d27c9aea80365dab	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-4-Carboxymethylenebut-2-en-4-olide 10V, Negative-QTOF	splash10-000b-9400000000-b7f9b56049121a6c58e7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-4-Carboxymethylenebut-2-en-4-olide 20V, Negative-QTOF	splash10-0002-9000000000-bb74108b75d88d650746	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-4-Carboxymethylenebut-2-en-4-olide 40V, Negative-QTOF	splash10-0uxu-9000000000-3ae3dd5a3949ebdd590f	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

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

120

PDB ID

Not Available

ChEBI ID

11972

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

trans-4-Carboxymethylenebut-2-en-4-olide + Water → 2-Maleylacetate	details

Showing metabocard for trans-4-Carboxymethylenebut-2-en-4-olide (HMDB0060518)

MOL for HMDB0060518 (trans-4-Carboxymethylenebut-2-en-4-olide)

3D MOL for HMDB0060518 (trans-4-Carboxymethylenebut-2-en-4-olide)

3D SDF for HMDB0060518 (trans-4-Carboxymethylenebut-2-en-4-olide)

3D-SDF for HMDB0060518 (trans-4-Carboxymethylenebut-2-en-4-olide)

PDB for HMDB0060518 (trans-4-Carboxymethylenebut-2-en-4-olide)

3D PDB for HMDB0060518 (trans-4-Carboxymethylenebut-2-en-4-olide)

SMILES for HMDB0060518 (trans-4-Carboxymethylenebut-2-en-4-olide)

INCHI for HMDB0060518 (trans-4-Carboxymethylenebut-2-en-4-olide)

Structure for HMDB0060518 (trans-4-Carboxymethylenebut-2-en-4-olide)

3D Structure for HMDB0060518 (trans-4-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