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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-11-30 15:52:45 UTC

Update Date

2023-02-21 17:17:58 UTC

HMDB ID

HMDB0013312

Secondary Accession Numbers

HMDB13312

Metabolite Identification

Common Name

trans-3-Octenedioic acid

Description

trans-3-Octenedioic 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 small amount of articles have been published on trans-3-Octenedioic acid.

Structure

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

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0       8.869 -21.282   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.409 -21.282   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.179 -22.615   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.719 -22.615   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.489 -23.949   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.029 -23.949   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.799 -25.283   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.339 -25.283   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      18.109 -26.617   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      18.109 -23.949   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       8.099 -19.948   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       8.099 -22.615   0.000  0.00  0.00           O+0
CONECT    1    2   11   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1                                                            
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
trans-3-Octenedioate	Generator
trans-3-Octene -1,8-dioate	HMDB
trans-3-Octene -1,8-dioic acid	HMDB
trans-3-Octene-1,8-dioiate	HMDB
trans-3-Octenedioiate	HMDB
(3E)-Oct-3-enedioate	Generator

Chemical Formula

C₈H₁₂O₄

Average Molecular Weight

172.1785

Monoisotopic Molecular Weight

172.073558872

IUPAC Name

(3E)-oct-3-enedioic acid

Traditional Name

(3E)-oct-3-enedioic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H12O4/c9-7(10)5-3-1-2-4-6-8(11)12/h1,3H,2,4-6H2,(H,9,10)(H,11,12)/b3-1+

InChI Key

QWWZNXBOJLOHGI-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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0013312)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0013312)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013312)

Source

Endogenous

Endogenous (HMDB: HMDB0013312)

Animal

Animal (HMDB: HMDB0013312)

Exogenous

Food

Food (HMDB: HMDB0013312)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0013312)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0013312)

Cellular process

Cell signaling (HMDB: HMDB0013312)

Biochemical process

Lipid transport (HMDB: HMDB0013312)

Role

Biological role

Energy storage (HMDB: HMDB0013312)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013312)

Pharmaceutical industry

Biomarker

Medium Chain Acyl Co A Dehydrogenase Deficiency (MarkerDB: MDB00029973)

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	3.04 g/L	ALOGPS
logP	1.01	ALOGPS
logP	1.02	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	4.05	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	6	ChemAxon
Refractivity	43.06 m³·mol⁻¹	ChemAxon
Polarizability	17.52 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	140.944	31661259
DarkChem	[M-H]-	136.908	31661259
DeepCCS	[M+H]+	132.903	30932474
DeepCCS	[M-H]-	129.074	30932474
DeepCCS	[M-2H]-	166.219	30932474
DeepCCS	[M+Na]+	141.653	30932474
AllCCS	[M+H]+	138.5	32859911
AllCCS	[M+H-H2O]+	134.6	32859911
AllCCS	[M+NH4]+	142.1	32859911
AllCCS	[M+Na]+	143.1	32859911
AllCCS	[M-H]-	138.0	32859911
AllCCS	[M+Na-2H]-	139.6	32859911
AllCCS	[M+HCOO]-	141.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
trans-3-Octenedioic acid	OC(=O)CCC\C=C\CC(O)=O	2594.5	Standard polar	33892256
trans-3-Octenedioic acid	OC(=O)CCC\C=C\CC(O)=O	1332.3	Standard non polar	33892256
trans-3-Octenedioic acid	OC(=O)CCC\C=C\CC(O)=O	1563.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
trans-3-Octenedioic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCC/C=C/CC(=O)O	1618.6	Semi standard non polar	33892256
trans-3-Octenedioic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)C/C=C/CCCC(=O)O	1619.0	Semi standard non polar	33892256
trans-3-Octenedioic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C/C=C/CCCC(=O)O[Si](C)(C)C	1689.0	Semi standard non polar	33892256
trans-3-Octenedioic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C/CC(=O)O	1866.8	Semi standard non polar	33892256
trans-3-Octenedioic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C/C=C/CCCC(=O)O	1862.3	Semi standard non polar	33892256
trans-3-Octenedioic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C	2150.8	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-3-Octenedioic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-006t-9200000000-9bda4daccea0c94ba554	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-3-Octenedioic acid GC-MS (2 TMS) - 70eV, Positive	splash10-006t-9730000000-4a24977789b6226b0490	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-3-Octenedioic 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-3-Octenedioic acid 10V, Positive-QTOF	splash10-0ab9-0900000000-80506768aa9d594be0c6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Octenedioic acid 20V, Positive-QTOF	splash10-0a6r-3900000000-e85beb2bb9f54e7ddd6e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Octenedioic acid 40V, Positive-QTOF	splash10-0gc0-9100000000-1b6622424a44ba223729	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Octenedioic acid 10V, Negative-QTOF	splash10-00di-0900000000-3b5890274a618a3778b5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Octenedioic acid 20V, Negative-QTOF	splash10-0fk9-0900000000-86dcd0e893c03155a7b0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Octenedioic acid 40V, Negative-QTOF	splash10-0a4l-9200000000-8392a616f5e3f797f3c7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Octenedioic acid 10V, Positive-QTOF	splash10-0a4i-3900000000-9f615067149aaf649407	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Octenedioic acid 20V, Positive-QTOF	splash10-0159-9100000000-bcd7d596f007fa1c541b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Octenedioic acid 40V, Positive-QTOF	splash10-0gb9-9000000000-bc65e58459c0d8e04de7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Octenedioic acid 10V, Negative-QTOF	splash10-00di-0900000000-12d84d80655c19cc06b4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Octenedioic acid 20V, Negative-QTOF	splash10-0a6r-0900000000-471c5124e9348bc19c34	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Octenedioic acid 40V, Negative-QTOF	splash10-0a4l-9100000000-7748b687479c27e3f8a1	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	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	0.197 +/- 0.394 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	1.313 +/- 1.970 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	22.983 +/- 19.699 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	4.597 +/- 3.283 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	7.223 +/- 1.970 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	5.91 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	21.669 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	65.664 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

FDB029376

KNApSAcK ID

Not Available

Chemspider ID

11431462

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22495178

PDB ID

Not Available

ChEBI ID

173786

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029973

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Jin SJ, Tserng KY: Metabolic origins of urinary unsaturated dicarboxylic acids. Biochemistry. 1990 Sep 18;29(37):8540-7. [PubMed:2271537 ]
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-3-Octenedioic acid (HMDB0013312)

MOL for HMDB0013312 (trans-3-Octenedioic acid)

3D MOL for HMDB0013312 (trans-3-Octenedioic acid)

3D SDF for HMDB0013312 (trans-3-Octenedioic acid)

3D-SDF for HMDB0013312 (trans-3-Octenedioic acid)

PDB for HMDB0013312 (trans-3-Octenedioic acid)

3D PDB for HMDB0013312 (trans-3-Octenedioic acid)

SMILES for HMDB0013312 (trans-3-Octenedioic acid)

INCHI for HMDB0013312 (trans-3-Octenedioic acid)

Structure for HMDB0013312 (trans-3-Octenedioic acid)

3D Structure for HMDB0013312 (trans-3-Octenedioic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra