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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-11-30 15:52:44 UTC

Update Date

2023-02-21 17:17:58 UTC

HMDB ID

HMDB0013311

Secondary Accession Numbers

HMDB13311

Metabolite Identification

Common Name

trans-2-Hexenedioic acid

Description

trans-2-Hexenedioic acid, also known as trans-2,3-dehydroadipate or (e)-hex-2-enedioic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Based on a literature review a significant number of articles have been published on trans-2-Hexenedioic acid.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(e)-Hex-2-enedioic acid	ChEBI
trans-2,3-Dehydroadipic acid	ChEBI
trans-2,3-Didehydroadipic acid	ChEBI
(e)-Hex-2-enedioate	Generator
trans-2,3-Dehydroadipate	Generator
trans-2,3-Didehydroadipate	Generator
trans-2-Hexenedioate	Generator
(2E)-Hex-2-enedioate	HMDB
(2E)-Hex-2-enedioic acid	HMDB

Chemical Formula

C₆H₈O₄

Average Molecular Weight

144.1253

Monoisotopic Molecular Weight

144.042258744

IUPAC Name

(2E)-hex-2-enedioic acid

Traditional Name

trans-β-hydromuconic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H8O4/c7-5(8)3-1-2-4-6(9)10/h1,3H,2,4H2,(H,7,8)(H,9,10)/b3-1+

InChI Key

HSBSUGYTMJWPAX-HNQUOIGGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-hexenedioic acid (CHEBI:49296 )
Dicarboxylic acids (LMFA01170070 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0013311)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0013311)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013311)

Source

Endogenous

Endogenous (HMDB: HMDB0013311)

Animal

Animal (HMDB: HMDB0013311)

Exogenous

Food

Food (HMDB: HMDB0013311)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0013311)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0013311)

Cellular process

Cell signaling (HMDB: HMDB0013311)

Biochemical process

Lipid transport (HMDB: HMDB0013311)

Role

Biological role

Energy storage (HMDB: HMDB0013311)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013311)

Pharmaceutical industry

Biomarker

Medium Chain Acyl Co A Dehydrogenase Deficiency (MarkerDB: MDB00029972)

Physical Properties

State

Solid

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	9.54 g/L	ALOGPS
logP	0.32	ALOGPS
logP	0.49	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	33.83 m³·mol⁻¹	ChemAxon
Polarizability	13.6 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
DarkChem	[M+H]+	132.6	31661259
DarkChem	[M-H]-	128.07	31661259
DeepCCS	[M+H]+	127.764	30932474
DeepCCS	[M-H]-	124.484	30932474
DeepCCS	[M-2H]-	161.267	30932474
DeepCCS	[M+Na]+	136.339	30932474
AllCCS	[M+H]+	132.1	32859911
AllCCS	[M+H-H2O]+	128.0	32859911
AllCCS	[M+NH4]+	135.9	32859911
AllCCS	[M+Na]+	137.0	32859911
AllCCS	[M-H]-	128.8	32859911
AllCCS	[M+Na-2H]-	130.9	32859911
AllCCS	[M+HCOO]-	133.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
trans-2-Hexenedioic acid	OC(=O)CC\C=C\C(O)=O	2437.1	Standard polar	33892256
trans-2-Hexenedioic acid	OC(=O)CC\C=C\C(O)=O	1140.3	Standard non polar	33892256
trans-2-Hexenedioic acid	OC(=O)CC\C=C\C(O)=O	1421.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
trans-2-Hexenedioic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC/C=C/C(=O)O	1467.8	Semi standard non polar	33892256
trans-2-Hexenedioic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)/C=C/CCC(=O)O	1485.3	Semi standard non polar	33892256
trans-2-Hexenedioic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C/CCC(=O)O[Si](C)(C)C	1537.3	Semi standard non polar	33892256
trans-2-Hexenedioic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC/C=C/C(=O)O	1723.9	Semi standard non polar	33892256
trans-2-Hexenedioic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)/C=C/CCC(=O)O	1726.3	Semi standard non polar	33892256
trans-2-Hexenedioic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C/CCC(=O)O[Si](C)(C)C(C)(C)C	1979.9	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-2-Hexenedioic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-9200000000-e999c41efa4ddf24c00a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-2-Hexenedioic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9830000000-f1b33bdcaa5eaaefce36	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-2-Hexenedioic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-2-Hexenedioic acid 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-2-Hexenedioic acid 10V, Positive-QTOF	splash10-004j-1900000000-4c92e1966212431b13b3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenedioic acid 20V, Positive-QTOF	splash10-002b-9800000000-4882ce5383961e543dee	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenedioic acid 40V, Positive-QTOF	splash10-0f79-9000000000-a4044e1226bb8f523335	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenedioic acid 10V, Negative-QTOF	splash10-0006-1900000000-30a2e879a2c6d5912284	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenedioic acid 20V, Negative-QTOF	splash10-002f-4900000000-67db21d7173b3c541b72	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenedioic acid 40V, Negative-QTOF	splash10-0a4l-9100000000-b4cd23c90fabb262ddb5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenedioic acid 10V, Negative-QTOF	splash10-0007-7900000000-80b809038ce6ea18268e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenedioic acid 20V, Negative-QTOF	splash10-001i-9300000000-69bc99b12ac3331dbebc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenedioic acid 40V, Negative-QTOF	splash10-001l-9000000000-9b70701f31edf163980f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenedioic acid 10V, Positive-QTOF	splash10-0032-9500000000-58af847a9e7e87a0a46a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenedioic acid 20V, Positive-QTOF	splash10-001r-9100000000-fca272bd90499fb767ee	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-2-Hexenedioic acid 40V, Positive-QTOF	splash10-0ktu-9000000000-1292dac9c4342adc06ea	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	0 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	0.784 +/- 1.569 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	10.198 +/- 7.0601 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	4.707 +/- 0.784 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	6.276 +/- 1.569 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	0 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	0 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	9.413 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	38.438 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details

Associated Disorders and Diseases

Disease References

Medium Chain Acyl-CoA Dehydrogenase Deficiency
Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. [PubMed:2380628 ]

Associated OMIM IDs

201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029375

KNApSAcK ID

Not Available

Chemspider ID

9052499

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10877230

PDB ID

Not Available

ChEBI ID

49296

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029972

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Jin SJ, Tserng KY: Identification of isomeric unsaturated medium-chain dicarboxylic acids in human urine. J Lipid Res. 1989 Oct;30(10):1611-9. [PubMed:2614263 ]
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.

Showing metabocard for trans-2-Hexenedioic acid (HMDB0013311)

MOL for HMDB0013311 (trans-2-Hexenedioic acid)

3D MOL for HMDB0013311 (trans-2-Hexenedioic acid)

3D SDF for HMDB0013311 (trans-2-Hexenedioic acid)

3D-SDF for HMDB0013311 (trans-2-Hexenedioic acid)

PDB for HMDB0013311 (trans-2-Hexenedioic acid)

3D PDB for HMDB0013311 (trans-2-Hexenedioic acid)

SMILES for HMDB0013311 (trans-2-Hexenedioic acid)

INCHI for HMDB0013311 (trans-2-Hexenedioic acid)

Structure for HMDB0013311 (trans-2-Hexenedioic acid)

3D Structure for HMDB0013311 (trans-2-Hexenedioic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra