MiMeDB: Showing metabocard for (2E)-oct-2-enedioic acid (MMDBc0050229)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 19:52:23 UTC

Update Date

2024-10-17 05:21:24 UTC

Metabolite ID

MMDBc0050229

Metabolite Identification

Common Name

(2E)-oct-2-enedioic acid

Description

2-Octenedioic acid is an unsaturated dicarboxylic acid found in the urine of persons with abnormal fatty acid metabolism, such as patients with Dicarboxylic aciduria (PMID 2094705 , 2614263 ).

Structure

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

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      19.439 -20.443   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      18.105 -22.753   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.436 -21.213   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.770 -18.903   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      14.104 -20.443   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.438 -21.213   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.771 -21.213   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.772 -20.443   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.437 -20.443   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.105 -21.213   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.103 -21.213   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.770 -20.443   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    1    2    8                                                  
CONECT   11    9   12                                                       
CONECT   12    3    4   11                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

Synonyms

Value	Source
2-Octenedioate	Generator
1-Hexene-1,6-dicarboxylate	HMDB
1-Hexene-1,6-dicarboxylic acid	HMDB
(2E)-Oct-2-enedioate	HMDB

Molecular Formula

C₈H₁₂O₄

Average Mass

172.1785

Monoisotopic Mass

172.073558872

IUPAC Name

(2E)-oct-2-enedioic acid

Traditional Name

(E)-oct-2-enedioic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCCC\C=C\C(O)=O

InChI Identifier

InChI=1S/C8H12O4/c9-7(10)5-3-1-2-4-6-8(11)12/h3,5H,1-2,4,6H2,(H,9,10)(H,11,12)/b5-3+

InChI Key

BNTPVRGYUHJFHN-HWKANZROSA-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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.06 g/L	ALOGPS
logP	1.14	ALOGPS
logP	1.38	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	4.15	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	43.03 m³·mol⁻¹	ChemAxon
Polarizability	17.61 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000e-9300000000-f1a09c8baab1ebacd19e	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00fr-9741000000-56f639d2fb2625d3cdbb	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-2900000000-9b5e8c7acbeffa7a7bff	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-aa84fcbe642b74aa9e12	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-016u-9000000000-a9bca1da2edcacdb888a	2012-07-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-3b5890274a618a3778b5	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fk9-0900000000-0fe0b507570004cbecf9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9300000000-45583d6735565af2116f	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-babb20dbeb5c909004f2	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a6r-1900000000-5b13ae6b7c8afdc726c1	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pc3-9100000000-e4e183c717cd0420d580	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-0900000000-80506768aa9d594be0c6	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-2900000000-74cc16e06c099daad389	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-015i-9100000000-08861ade868bf4d03dfa	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0bt9-2900000000-364a4d0b62fbc3892c43	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015a-9200000000-bf9c4f003c6d7f93b5fc	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbc-9000000000-337718fabcf3039c5d04	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Evidence Type	Host and Biospecimen	Data Source	Reference
Medium chain acyl-coa dehydrogenase deficiency	Association	Human Urine	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Medium chain acyl-coa dehydrogenase deficiency	Association	Human Urine	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Medium chain acyl-coa dehydrogenase deficiency	Association	Human Urine	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003
Medium chain acyl-coa dehydrogenase deficiency	Association	Human Urine	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human

Exposure Sources

Source Type	Activity	Data Source	Reference
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	7			umol/mmol creatinine	Adult (>18 years old)	Both	Medium Chain Acyl-CoA Dehydrogenase Deficiency	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Urine	Detected and Quantified	125.00	0.00	250.00	umol/mmol creatinine	Children (1-13 years old)	Both	Medium chain acyl-CoA dehydrogenase deficiency (MCAD)	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Urine	Detected and Quantified		0	1	umol/mmol creatinine	Newborn (0-30 days old)	Both	Medium Chain Acyl-CoA Dehydrogenase Deficiency	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003
Human Urine	Detected and Quantified		0	2.8	umol/mmol creatinine	Children (1-13 years old)	Both	Medium Chain Acyl-CoA Dehydrogenase Deficiency	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003
Human Blood	Detected but not Quantified								HMDB

External Links

HMDB ID

HMDB0000341

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021965

KNApSAcK ID

C00007508

Chemspider ID

4800646

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5330

PubChem Compound

6079438

PDB ID

Not Available

ChEBI ID

89192

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Pitt JJ: Gas chromatographic-mass spectrometric characterisation of unsaturated dicarboxylic acids in urine. J Chromatogr. 1990 Dec 14;534:182-9. doi: 10.1016/s0378-4347(00)82160-x. [PubMed:2094705 ]
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 ]

Showing metabocard for (2E)-oct-2-enedioic acid (MMDBc0050229)

MOL for #<Metabolite:0x00007fdb71285b00>

3D MOL for #<Metabolite:0x00007fdb71285b00>

3D SDF for #<Metabolite:0x00007fdb71285b00>

3D-SDF for #<Metabolite:0x00007fdb71285b00>

PDB for #<Metabolite:0x00007fdb71285b00>

3D PDB for #<Metabolite:0x00007fdb71285b00>

SMILES for #<Metabolite:0x00007fdb71285b00>

INCHI for #<Metabolite:0x00007fdb71285b00>

Structure for #<Metabolite:0x00007fdb71285b00>

3D Structure for #<Metabolite:0x00007fdb71285b00>