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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

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:17:05 UTC

HMDB ID

HMDB0004982

Secondary Accession Numbers

HMDB04982

Metabolite Identification

Common Name

cis-4-Octenedioic acid

Description

cis-4-Octenedioic acid, also known as (Z)-4-octene-1,8-dioate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. cis-4-Octenedioic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.

Structure

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

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-5                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    8    6                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9                                                            
CONECT   11    2                                                            
CONECT   12    9                                                            
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
cis-4-Octenedioate	Generator
(Z)-4-Octene-1,8-dioate	HMDB
(Z)-4-Octene-1,8-dioic acid	HMDB
cis-4-Octene-1,8-dioate	HMDB
cis-4-Octene-1,8-dioic acid	HMDB

Chemical Formula

C₈H₁₂O₄

Average Molecular Weight

172.1785

Monoisotopic Molecular Weight

172.073558872

IUPAC Name

(4Z)-oct-4-enedioic acid

Traditional Name

cis-4-octenedioic acid

CAS Registry Number

38561-68-1

SMILES

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

InChI Identifier

InChI=1S/C8H12O4/c9-7(10)5-3-1-2-4-6-8(11)12/h1-2H,3-6H2,(H,9,10)(H,11,12)/b2-1-

InChI Key

LQVYKEXVMZXOAH-UPHRSURJSA-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

Dicarboxylic acids (LMFA01170078 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0004982)

Excreta

Biofluid or Excreta

Urine (PMID: 2380628)

Cellular substructure

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Medium Chain Acyl Co A Dehydrogenase Deficiency (MarkerDB: MDB00030010)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	96 - 98 °C	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	3.16 g/L	ALOGPS
logP	0.96	ALOGPS
logP	1.02	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	4.08	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	17.2 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]+	139.995	31661259
DarkChem	[M-H]-	135.4	31661259
DeepCCS	[M+H]+	136.88	30932474
DeepCCS	[M-H]-	133.053	30932474
DeepCCS	[M-2H]-	170.059	30932474
DeepCCS	[M+Na]+	145.599	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]-	137.9	32859911
AllCCS	[M+Na-2H]-	139.4	32859911
AllCCS	[M+HCOO]-	141.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cis-4-Octenedioic acid	OC(=O)CC\C=C/CCC(O)=O	2577.1	Standard polar	33892256
cis-4-Octenedioic acid	OC(=O)CC\C=C/CCC(O)=O	1307.3	Standard non polar	33892256
cis-4-Octenedioic acid	OC(=O)CC\C=C/CCC(O)=O	1572.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cis-4-Octenedioic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC/C=C\CCC(=O)O	1608.8	Semi standard non polar	33892256
cis-4-Octenedioic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC/C=C\CCC(=O)O[Si](C)(C)C	1648.8	Semi standard non polar	33892256
cis-4-Octenedioic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC/C=C\CCC(=O)O	1857.4	Semi standard non polar	33892256
cis-4-Octenedioic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C	2096.6	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 - cis-4-Octenedioic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-002b-9700000000-05fd068ced2272cfd647	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-4-Octenedioic acid GC-MS (2 TMS) - 70eV, Positive	splash10-009i-9520000000-59e3c21041662007d302	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-4-Octenedioic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-4-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
Experimental LC-MS/MS	LC-MS/MS Spectrum - cis-4-Octenedioic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-052r-0900000000-dcb0faa12f86c5e6d354	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - cis-4-Octenedioic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-001i-9100000000-2fb14d29c61748d9bc25	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - cis-4-Octenedioic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-00ou-9000000000-ad3de6e6bc5dc675f293	2012-07-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-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 - cis-4-Octenedioic acid 20V, Positive-QTOF	splash10-0a6r-4900000000-e9ac05a7cafb49b272ac	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Octenedioic acid 40V, Positive-QTOF	splash10-0gb9-9100000000-b4faa4cd8c9b56b4113d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-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 - cis-4-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 - cis-4-Octenedioic acid 40V, Negative-QTOF	splash10-0a4l-9200000000-0f20f53f84cb306f481e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Octenedioic acid 10V, Negative-QTOF	splash10-00di-0900000000-12d84d80655c19cc06b4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Octenedioic acid 20V, Negative-QTOF	splash10-0a6r-1900000000-8e3dbdc5ba018c73aacb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Octenedioic acid 40V, Negative-QTOF	splash10-0a7l-9100000000-a55b6694ae01f5c2d1e2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Octenedioic acid 10V, Positive-QTOF	splash10-0a4i-3900000000-20531fc91cac7e3fdfe2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Octenedioic acid 20V, Positive-QTOF	splash10-0159-9100000000-846f91a14695d48f522c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Octenedioic acid 40V, Positive-QTOF	splash10-0gb9-9000000000-b608a016425fd1126b87	2021-09-24	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
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	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

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	0.65 +/- 0.65 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	2380628	details
Urine	Detected and Quantified	0.657 +/- 0.657 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	0.657 +/- 0.657 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	1.970 +/- 3.283 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	2380628	details
Urine	Detected and Quantified	11.163 +/- 7.880 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	5.253 +/- 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	4.597 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	5.253 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	13.133 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	37.429 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	127.389 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	45.902-261.960 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	6434845	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 ] Duran M, De Klerk JB, Wadman SK, Bruinvis L, Ketting D: The differential diagnosis of dicarboxylic aciduria. J Inherit Metab Dis. 1984;7 Suppl 1:48-51. [PubMed:6434845 ]

Associated OMIM IDs

201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023569

KNApSAcK ID

Not Available

Chemspider ID

9979870

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

7235

PubChem Compound

11805205

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00030010

Good Scents ID

Not Available

References

Synthesis Reference

Barco, A.; Benetti, S.; Pollini, G. P.; Taddia, R. Synthesis of cis-4-octene-1,8-dioic acid and its esters. Organic Preparations and Procedures International (1974), 6(5), 217-20.

Material Safety Data Sheet (MSDS)

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. [PubMed:2094705 ]

Showing metabocard for cis-4-Octenedioic acid (HMDB0004982)

MOL for HMDB0004982 (cis-4-Octenedioic acid)

3D MOL for HMDB0004982 (cis-4-Octenedioic acid)

3D SDF for HMDB0004982 (cis-4-Octenedioic acid)

3D-SDF for HMDB0004982 (cis-4-Octenedioic acid)

PDB for HMDB0004982 (cis-4-Octenedioic acid)

3D PDB for HMDB0004982 (cis-4-Octenedioic acid)

SMILES for HMDB0004982 (cis-4-Octenedioic acid)

INCHI for HMDB0004982 (cis-4-Octenedioic acid)

Structure for HMDB0004982 (cis-4-Octenedioic acid)

3D Structure for HMDB0004982 (cis-4-Octenedioic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra