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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:18:42 UTC

Update Date

2023-02-21 17:26:48 UTC

HMDB ID

HMDB0038965

Secondary Accession Numbers

HMDB38965

Metabolite Identification

Common Name

(E)-10-Hydroxy-2-decene-4,6-diynoic acid

Description

(E)-10-Hydroxy-2-decene-4,6-diynoic acid, also known as (2E)-10-hydroxydec-2-en-4,6-diynoate, 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 (E)-10-Hydroxy-2-decene-4,6-diynoic acid.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       3.850   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.080   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.620   5.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.390   6.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.930   6.668   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.700   8.002   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.240   8.002   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12   13                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-10-Hydroxy-2-decene-4,6-diynoate	Generator
(2E)-10-Hydroxydec-2-en-4,6-diynoate	HMDB

Chemical Formula

C₁₀H₁₀O₃

Average Molecular Weight

178.1846

Monoisotopic Molecular Weight

178.062994186

IUPAC Name

(2E)-10-hydroxydec-2-en-4,6-diynoic acid

Traditional Name

(2E)-10-hydroxydec-2-en-4,6-diynoic acid

CAS Registry Number

Not Available

SMILES

OCCCC#CC#C\C=C\C(O)=O

InChI Identifier

InChI=1S/C10H10O3/c11-9-7-5-3-1-2-4-6-8-10(12)13/h6,8,11H,5,7,9H2,(H,12,13)/b8-6+

InChI Key

FFWLSJVIZWBSTJ-SOFGYWHQSA-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
Hydroxy fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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: HMDB0038965)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0038965)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038965)

Source

Endogenous

Endogenous (HMDB: HMDB0038965)

Plant

Plant (HMDB: HMDB0038965)

Animal

Animal (HMDB: HMDB0038965)

Exogenous

Food

Food (HMDB: HMDB0038965)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0038965)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038965)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038965)

Lipid metabolism pathway (HMDB: HMDB0038965)

Biochemical process

Lipid transport (HMDB: HMDB0038965)

Role

Biological role

Energy source (HMDB: HMDB0038965)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	154.5 - 156 °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	0.054 g/L	ALOGPS
logP	1.62	ALOGPS
logP	1.32	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	3.67	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	51.22 m³·mol⁻¹	ChemAxon
Polarizability	19.43 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]+	144.052	31661259
DarkChem	[M-H]-	144.056	31661259
DeepCCS	[M+H]+	134.218	30932474
DeepCCS	[M-H]-	130.387	30932474
DeepCCS	[M-2H]-	167.464	30932474
DeepCCS	[M+Na]+	142.854	30932474
AllCCS	[M+H]+	137.9	32859911
AllCCS	[M+H-H2O]+	134.0	32859911
AllCCS	[M+NH4]+	141.6	32859911
AllCCS	[M+Na]+	142.7	32859911
AllCCS	[M-H]-	139.4	32859911
AllCCS	[M+Na-2H]-	140.6	32859911
AllCCS	[M+HCOO]-	141.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E)-10-Hydroxy-2-decene-4,6-diynoic acid	OCCCC#CC#C\C=C\C(O)=O	3057.5	Standard polar	33892256
(E)-10-Hydroxy-2-decene-4,6-diynoic acid	OCCCC#CC#C\C=C\C(O)=O	1740.6	Standard non polar	33892256
(E)-10-Hydroxy-2-decene-4,6-diynoic acid	OCCCC#CC#C\C=C\C(O)=O	1897.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E)-10-Hydroxy-2-decene-4,6-diynoic acid,1TMS,isomer #1	C[Si](C)(C)OCCCC#CC#C/C=C/C(=O)O	1949.5	Semi standard non polar	33892256
(E)-10-Hydroxy-2-decene-4,6-diynoic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)/C=C/C#CC#CCCCO	1912.6	Semi standard non polar	33892256
(E)-10-Hydroxy-2-decene-4,6-diynoic acid,2TMS,isomer #1	C[Si](C)(C)OCCCC#CC#C/C=C/C(=O)O[Si](C)(C)C	2012.3	Semi standard non polar	33892256
(E)-10-Hydroxy-2-decene-4,6-diynoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCC#CC#C/C=C/C(=O)O	2184.3	Semi standard non polar	33892256
(E)-10-Hydroxy-2-decene-4,6-diynoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C#CC#CCCCO	2146.3	Semi standard non polar	33892256
(E)-10-Hydroxy-2-decene-4,6-diynoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCC#CC#C/C=C/C(=O)O[Si](C)(C)C(C)(C)C	2443.9	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 - (E)-10-Hydroxy-2-decene-4,6-diynoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ec-5900000000-a9608586f5e5fc1b2d5c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-10-Hydroxy-2-decene-4,6-diynoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9251000000-487649c3234d8f9dc49a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-10-Hydroxy-2-decene-4,6-diynoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-10-Hydroxy-2-decene-4,6-diynoic 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 - (E)-10-Hydroxy-2-decene-4,6-diynoic acid 10V, Positive-QTOF	splash10-03fr-0900000000-285bf768baaf5de4936e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-10-Hydroxy-2-decene-4,6-diynoic acid 20V, Positive-QTOF	splash10-02t9-2900000000-838c21d45d19ed2c0412	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-10-Hydroxy-2-decene-4,6-diynoic acid 40V, Positive-QTOF	splash10-0v00-9400000000-ceff6d435bbd515f8bb7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-10-Hydroxy-2-decene-4,6-diynoic acid 10V, Negative-QTOF	splash10-004i-0900000000-b65234e65a9db7edd4f9	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-10-Hydroxy-2-decene-4,6-diynoic acid 20V, Negative-QTOF	splash10-056r-1900000000-dcdf14483241f51e89bc	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-10-Hydroxy-2-decene-4,6-diynoic acid 40V, Negative-QTOF	splash10-052f-9500000000-e56edd2a6b73af8777ff	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-10-Hydroxy-2-decene-4,6-diynoic acid 10V, Positive-QTOF	splash10-0059-4900000000-f38a6068127b9a9499fa	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-10-Hydroxy-2-decene-4,6-diynoic acid 20V, Positive-QTOF	splash10-00p0-9300000000-a41cd346204252d05738	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-10-Hydroxy-2-decene-4,6-diynoic acid 40V, Positive-QTOF	splash10-004r-9200000000-9a2f1d6ab181bdb6c66e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-10-Hydroxy-2-decene-4,6-diynoic acid 10V, Negative-QTOF	splash10-004i-0900000000-ac193e5d5157f593692d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-10-Hydroxy-2-decene-4,6-diynoic acid 20V, Negative-QTOF	splash10-0lgr-3900000000-e2f51f34de2b258d07ed	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-10-Hydroxy-2-decene-4,6-diynoic acid 40V, Negative-QTOF	splash10-03mr-9400000000-f46d80eb8e2d89701535	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

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB018451

KNApSAcK ID

Not Available

Chemspider ID

30777310

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101411738

PDB ID

Not Available

ChEBI ID

Not Available

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

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (E)-10-Hydroxy-2-decene-4,6-diynoic acid (HMDB0038965)

MOL for HMDB0038965 ((E)-10-Hydroxy-2-decene-4,6-diynoic acid)

3D MOL for HMDB0038965 ((E)-10-Hydroxy-2-decene-4,6-diynoic acid)

3D SDF for HMDB0038965 ((E)-10-Hydroxy-2-decene-4,6-diynoic acid)

3D-SDF for HMDB0038965 ((E)-10-Hydroxy-2-decene-4,6-diynoic acid)

PDB for HMDB0038965 ((E)-10-Hydroxy-2-decene-4,6-diynoic acid)

3D PDB for HMDB0038965 ((E)-10-Hydroxy-2-decene-4,6-diynoic acid)

SMILES for HMDB0038965 ((E)-10-Hydroxy-2-decene-4,6-diynoic acid)

INCHI for HMDB0038965 ((E)-10-Hydroxy-2-decene-4,6-diynoic acid)

Structure for HMDB0038965 ((E)-10-Hydroxy-2-decene-4,6-diynoic acid)

3D Structure for HMDB0038965 ((E)-10-Hydroxy-2-decene-4,6-diynoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra