cis-4-carboxymethylenebut-2-en-4-olide (YMDB00159)

Identification

YMDB ID

YMDB00159

Name

cis-4-carboxymethylenebut-2-en-4-olide

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

cis-4-Carboxymethylenebut-2-en-4-olide, also known as (5-oxo-2(5H)-furanylidene)acetic acid, belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. cis-4-Carboxymethylenebut-2-en-4-olide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

(5-oxo-2(5H)-furanylidene)acetic acid
4-Carboxymethylenebut-2-en-4-olide
cis-4-Carboxymethylenebut-2-en-4-olide
(5-oxo-2(5H)-Furanylidene)acetate
Dienelactone
cis-Dienelactone

CAS number

73237-79-3

Weight

Average: 140.0936
Monoisotopic: 140.010958616

InChI Key

AYFXPGXAZMFWNH-ONEGZZNKSA-N

InChI

InChI=1S/C6H4O4/c7-5(8)3-4-1-2-6(9)10-4/h1-3H,(H,7,8)/b4-3+

IUPAC Name

2-[(2E)-5-oxo-2,5-dihydrofuran-2-ylidene]acetic acid

Traditional IUPAC Name

[(2E)-5-oxofuran-2-ylidene]acetic acid

Chemical Formula

C₆H₄O₄

SMILES

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

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

4-carboxymethylenebut-2-en-4-olide (CHEBI:18371 )

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted 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	11.91 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fb9-9100000000-a9372b7bcb64119f38d0	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9600000000-40562b3dbdce53cefdb4	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-4da24f4d3150d4cb0d9c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-2900000000-285620f88db9e73b5ead	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0umi-9300000000-c40d20cf666aab67a491	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000j-5900000000-34a6a177544dbc512389	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0072-9600000000-42a684d27e1e540b3b12	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f95-9000000000-ff8b053604593c0325bb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9400000000-32ec3f966c201e73e6b7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9100000000-acf0d7874c4fc167d1fa	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-f749d27c9aea80365dab	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000b-9400000000-b7f9b56049121a6c58e7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9000000000-bb74108b75d88d650746	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uxu-9000000000-3ae3dd5a3949ebdd590f	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	18371
HMDB ID	HMDB0060459
Pubchem Compound ID	5459914
Kegg ID	C04431
ChemSpider ID	4573642
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Putative carboxymethylenebutenolidase

General function:: Involved in hydrolase activity
Specific function:: 4-carboxymethylenebut-2-en-4-olide + H(2)O = 4-oxohex-2-enedioate
Gene Name:: Not Available
Uniprot ID:: Q07505
Molecular weight:: 30836.90039

Reactions

4-carboxymethylenebut-2-en-4-olide + H(2)O → 4-oxohex-2-enedioate.

cis-4-carboxymethylenebut-2-en-4-olide (YMDB00159)

Structure for #<Compound:0xaadb4228>

Enzymes

Reactions