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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 00:55:30 UTC

Update Date

2023-02-21 17:29:53 UTC

HMDB ID

HMDB0060348

Secondary Accession Numbers

HMDB60348

Metabolite Identification

Common Name

2-Maleylacetate

Description

2-Maleylacetate, also known as maleylacetic acid, belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. 2-Maleylacetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(Z)-4-oxo-2-Hexenedioic acid	ChEBI
4-Oxohex-2-enedioate	ChEBI
Maleylacetate	ChEBI
(Z)-4-oxo-2-Hexenedioate	Generator
4-Oxohex-2-enedioic acid	Generator
Maleylacetic acid	Generator
2-Maleylacetic acid	Generator
Maleoylacetic acid	MeSH

Chemical Formula

C₆H₆O₅

Average Molecular Weight

158.1088

Monoisotopic Molecular Weight

158.021523302

IUPAC Name

(2Z)-4-oxohex-2-enedioic acid

Traditional Name

maleylacetic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC(=O)\C=C/C(O)=O

InChI Identifier

InChI=1S/C6H6O5/c7-4(3-6(10)11)1-2-5(8)9/h1-2H,3H2,(H,8,9)(H,10,11)/b2-1-

InChI Key

SOXXPQLIZIPMIZ-UPHRSURJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-chain keto acids and derivatives

Alternative Parents

Substituents

Medium-chain keto acid
Beta-keto acid
B'-hydroxy-alpha,beta-unsaturated-ketone
Fatty acyl
Beta-hydroxy ketone
Dicarboxylic acid or derivatives
1,3-dicarbonyl compound
Unsaturated fatty acid
Acryloyl-group
Alpha,beta-unsaturated ketone
Enone
Ketone
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

4-oxohex-2-enedioic acid (CHEBI:1184 )

Ontology

Not Available

Exogenous (HMDB: HMDB0060348)

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	7.25 g/L	ALOGPS
logP	-0.06	ALOGPS
logP	0.18	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	2.71	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	34.5 m³·mol⁻¹	ChemAxon
Polarizability	13.16 Å³	ChemAxon
Number of Rings	0	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]+	129.448	30932474
DeepCCS	[M-H]-	125.618	30932474
DeepCCS	[M-2H]-	162.843	30932474
DeepCCS	[M+Na]+	138.383	30932474
AllCCS	[M+H]+	134.2	32859911
AllCCS	[M+H-H2O]+	130.1	32859911
AllCCS	[M+NH4]+	137.9	32859911
AllCCS	[M+Na]+	139.0	32859911
AllCCS	[M-H]-	128.5	32859911
AllCCS	[M+Na-2H]-	130.2	32859911
AllCCS	[M+HCOO]-	132.1	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.	2.69 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9434 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.35 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	903.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	348.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	68.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	207.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	66.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	263.7 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	322.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	271.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	652.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	132.6 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	973.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	230.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	227.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	742.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	255.2 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	323.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Maleylacetate	OC(=O)CC(=O)\C=C/C(O)=O	2725.0	Standard polar	33892256
2-Maleylacetate	OC(=O)CC(=O)\C=C/C(O)=O	1200.5	Standard non polar	33892256
2-Maleylacetate	OC(=O)CC(=O)\C=C/C(O)=O	1588.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Maleylacetate,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC(=O)/C=C\C(=O)O	1585.1	Semi standard non polar	33892256
2-Maleylacetate,1TMS,isomer #2	C[Si](C)(C)OC(=O)/C=C\C(=O)CC(=O)O	1551.7	Semi standard non polar	33892256
2-Maleylacetate,1TMS,isomer #3	C[Si](C)(C)OC(=CC(=O)O)/C=C\C(=O)O	1750.3	Semi standard non polar	33892256
2-Maleylacetate,2TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C\C(=O)CC(=O)O[Si](C)(C)C	1641.9	Semi standard non polar	33892256
2-Maleylacetate,2TMS,isomer #2	C[Si](C)(C)OC(=O)C=C(/C=C\C(=O)O)O[Si](C)(C)C	1813.0	Semi standard non polar	33892256
2-Maleylacetate,2TMS,isomer #3	C[Si](C)(C)OC(=O)/C=C\C(=CC(=O)O)O[Si](C)(C)C	1809.0	Semi standard non polar	33892256
2-Maleylacetate,3TMS,isomer #1	C[Si](C)(C)OC(=O)C=C(/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1821.5	Semi standard non polar	33892256
2-Maleylacetate,3TMS,isomer #1	C[Si](C)(C)OC(=O)C=C(/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1741.0	Standard non polar	33892256
2-Maleylacetate,3TMS,isomer #1	C[Si](C)(C)OC(=O)C=C(/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1792.3	Standard polar	33892256
2-Maleylacetate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(=O)/C=C\C(=O)O	1820.8	Semi standard non polar	33892256
2-Maleylacetate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=O)CC(=O)O	1786.9	Semi standard non polar	33892256
2-Maleylacetate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CC(=O)O)/C=C\C(=O)O	1980.6	Semi standard non polar	33892256
2-Maleylacetate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=O)CC(=O)O[Si](C)(C)C(C)(C)C	2093.7	Semi standard non polar	33892256
2-Maleylacetate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C=C(/C=C\C(=O)O)O[Si](C)(C)C(C)(C)C	2273.6	Semi standard non polar	33892256
2-Maleylacetate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=CC(=O)O)O[Si](C)(C)C(C)(C)C	2314.1	Semi standard non polar	33892256
2-Maleylacetate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C=C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2506.6	Semi standard non polar	33892256
2-Maleylacetate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C=C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2350.8	Standard non polar	33892256
2-Maleylacetate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C=C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2148.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Maleylacetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9200000000-6cbb9b4c6c7936d0cff9	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Maleylacetate GC-MS (2 TMS) - 70eV, Positive	splash10-022i-9860000000-61befd7ba0403872d1ae	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Maleylacetate 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-Maleylacetate 10V, Positive-QTOF	splash10-0006-1900000000-9f4bd73246c1ec182e88	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Maleylacetate 20V, Positive-QTOF	splash10-01vn-7900000000-eee90ce719bbc702b1c3	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Maleylacetate 40V, Positive-QTOF	splash10-006t-9100000000-9e9070ad596a90e7503f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Maleylacetate 10V, Negative-QTOF	splash10-0bti-3900000000-2025e2328c5b1fbdc64f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Maleylacetate 20V, Negative-QTOF	splash10-08fs-9600000000-ae443a75a844ee0bd1da	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Maleylacetate 40V, Negative-QTOF	splash10-066v-9100000000-1414fa6f2dc1874da3eb	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Maleylacetate 10V, Positive-QTOF	splash10-0005-9600000000-9039551339c09bdfdca5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Maleylacetate 20V, Positive-QTOF	splash10-05mk-9000000000-1355e25670468c555e84	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Maleylacetate 40V, Positive-QTOF	splash10-00kf-9000000000-a445bad55c5cecfc7f5a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Maleylacetate 10V, Negative-QTOF	splash10-02t9-9600000000-c53bd6320b75c2dc6909	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Maleylacetate 20V, Negative-QTOF	splash10-014i-9100000000-36a3c561086be0ee94d3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Maleylacetate 40V, Negative-QTOF	splash10-014i-9000000000-862eaff8183941aa3ff2	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

C00013593

Chemspider ID

4444140

KEGG Compound ID

C02222

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Maleylacetic acid

METLIN ID

Not Available

PubChem Compound

5280500

PDB ID

Not Available

ChEBI ID

1184

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

cis-4-Carboxymethylenebut-2-en-4-olide + Water → 2-Maleylacetate	details
trans-4-Carboxymethylenebut-2-en-4-olide + Water → 2-Maleylacetate	details
5-Fluoromuconolactone + Water → 2-Maleylacetate + Fluoride	details
4-Fluoromuconolactone + Water → 2-Maleylacetate + Fluoride	details

Showing metabocard for 2-Maleylacetate (HMDB0060348)

MOL for HMDB0060348 (2-Maleylacetate)

3D MOL for HMDB0060348 (2-Maleylacetate)

3D SDF for HMDB0060348 (2-Maleylacetate)

3D-SDF for HMDB0060348 (2-Maleylacetate)

PDB for HMDB0060348 (2-Maleylacetate)

3D PDB for HMDB0060348 (2-Maleylacetate)

SMILES for HMDB0060348 (2-Maleylacetate)

INCHI for HMDB0060348 (2-Maleylacetate)

Structure for HMDB0060348 (2-Maleylacetate)

3D Structure for HMDB0060348 (2-Maleylacetate)

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