Jump To Section:

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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:40:42 UTC

Update Date

2023-02-21 17:19:52 UTC

HMDB ID

HMDB0031055

Secondary Accession Numbers

HMDB31055

Metabolite Identification

Common Name

(Z)-10-Hydroxy-8-decene-4,6-diynoic acid

Description

(Z)-10-Hydroxy-8-decene-4,6-diynoic acid, also known as (Z)-helianthenate F, 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 (Z)-10-Hydroxy-8-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       3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850  -4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.620  -5.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.390  -6.668   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.930  -6.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.700  -8.002   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.240  -8.002   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.930  -9.336   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
(Z)-10-Hydroxy-8-decene-4,6-diynoate	Generator
10-Hydroxy-8Z-decene-4,6-diynoate	HMDB
(Z)-Helianthenate F	HMDB

Chemical Formula

C₁₀H₁₀O₃

Average Molecular Weight

178.1846

Monoisotopic Molecular Weight

178.062994186

IUPAC Name

(8Z)-10-hydroxydec-8-en-4,6-diynoic acid

Traditional Name

(8Z)-10-hydroxydec-8-en-4,6-diynoic acid

CAS Registry Number

51193-97-6

SMILES

OC\C=C/C#CC#CCCC(O)=O

InChI Identifier

InChI=1S/C10H10O3/c11-9-7-5-3-1-2-4-6-8-10(12)13/h5,7,11H,6,8-9H2,(H,12,13)/b7-5-

InChI Key

JIPUTTVWDAXSEZ-ALCCZGGFSA-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

Unsaturated fatty acids (LMFA01030713 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0031055)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0031055)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031055)

Source

Endogenous

Endogenous (HMDB: HMDB0031055)

Plant

Plant (HMDB: HMDB0031055)

Animal

Animal (HMDB: HMDB0031055)

Exogenous

Food

Food (HMDB: HMDB0031055)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0031055)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0031055)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0031055)

Lipid metabolism pathway (HMDB: HMDB0031055)

Biochemical process

Lipid transport (HMDB: HMDB0031055)

Role

Biological role

Energy source (HMDB: HMDB0031055)

Physical Properties

State

Not Available

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	0.087 g/L	ALOGPS
logP	1.27	ALOGPS
logP	1.12	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.58	ChemAxon
pKa (Strongest Basic)	-2.5	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	51.09 m³·mol⁻¹	ChemAxon
Polarizability	18.95 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]+	144.556	31661259
DarkChem	[M-H]-	142.388	31661259
DeepCCS	[M+H]+	130.501	30932474
DeepCCS	[M-H]-	126.672	30932474
DeepCCS	[M-2H]-	163.729	30932474
DeepCCS	[M+Na]+	139.224	30932474
AllCCS	[M+H]+	137.9	32859911
AllCCS	[M+H-H2O]+	134.0	32859911
AllCCS	[M+NH4]+	141.5	32859911
AllCCS	[M+Na]+	142.6	32859911
AllCCS	[M-H]-	139.0	32859911
AllCCS	[M+Na-2H]-	140.1	32859911
AllCCS	[M+HCOO]-	141.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	4.39 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6771 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.24 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	48.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1589.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	315.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	108.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	199.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	111.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	386.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	381.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	113.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	818.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	297.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1091.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	258.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	546.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	259.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	129.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(Z)-10-Hydroxy-8-decene-4,6-diynoic acid	OC\C=C/C#CC#CCCC(O)=O	2940.3	Standard polar	33892256
(Z)-10-Hydroxy-8-decene-4,6-diynoic acid	OC\C=C/C#CC#CCCC(O)=O	1703.3	Standard non polar	33892256
(Z)-10-Hydroxy-8-decene-4,6-diynoic acid	OC\C=C/C#CC#CCCC(O)=O	1836.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(Z)-10-Hydroxy-8-decene-4,6-diynoic acid,1TMS,isomer #1	C[Si](C)(C)OC/C=C\C#CC#CCCC(=O)O	1946.3	Semi standard non polar	33892256
(Z)-10-Hydroxy-8-decene-4,6-diynoic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)CCC#CC#C/C=C\CO	1867.0	Semi standard non polar	33892256
(Z)-10-Hydroxy-8-decene-4,6-diynoic acid,2TMS,isomer #1	C[Si](C)(C)OC/C=C\C#CC#CCCC(=O)O[Si](C)(C)C	2004.7	Semi standard non polar	33892256
(Z)-10-Hydroxy-8-decene-4,6-diynoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC/C=C\C#CC#CCCC(=O)O	2176.3	Semi standard non polar	33892256
(Z)-10-Hydroxy-8-decene-4,6-diynoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC#CC#C/C=C\CO	2102.9	Semi standard non polar	33892256
(Z)-10-Hydroxy-8-decene-4,6-diynoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC/C=C\C#CC#CCCC(=O)O[Si](C)(C)C(C)(C)C	2415.6	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 - (Z)-10-Hydroxy-8-decene-4,6-diynoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ilc-3900000000-6bd34cc816a95acb7e33	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-10-Hydroxy-8-decene-4,6-diynoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-05j3-9361000000-b4d22d555ed141ce0870	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-10-Hydroxy-8-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 - (Z)-10-Hydroxy-8-decene-4,6-diynoic acid 10V, Positive-QTOF	splash10-03fr-0900000000-cf8b38307f25f09a0332	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-10-Hydroxy-8-decene-4,6-diynoic acid 20V, Positive-QTOF	splash10-02tc-2900000000-1d0379f462e619bbce46	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-10-Hydroxy-8-decene-4,6-diynoic acid 40V, Positive-QTOF	splash10-0v00-9300000000-2866d78469fc907e3ace	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-10-Hydroxy-8-decene-4,6-diynoic acid 10V, Negative-QTOF	splash10-004i-0900000000-1ba883145fd2122d7b4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-10-Hydroxy-8-decene-4,6-diynoic acid 20V, Negative-QTOF	splash10-056r-2900000000-e92191ccfa136abb112e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-10-Hydroxy-8-decene-4,6-diynoic acid 40V, Negative-QTOF	splash10-052f-9500000000-8bf033cf2168101c6b0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-10-Hydroxy-8-decene-4,6-diynoic acid 10V, Positive-QTOF	splash10-00n0-7900000000-85cd67c05b24aa8d7c5b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-10-Hydroxy-8-decene-4,6-diynoic acid 20V, Positive-QTOF	splash10-004r-9300000000-2ce313a5eeba5966d27c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-10-Hydroxy-8-decene-4,6-diynoic acid 40V, Positive-QTOF	splash10-004r-9200000000-939728b52f2f7709a6ab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-10-Hydroxy-8-decene-4,6-diynoic acid 10V, Negative-QTOF	splash10-004i-0900000000-7481e6c74c4c2d2def19	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-10-Hydroxy-8-decene-4,6-diynoic acid 20V, Negative-QTOF	splash10-0pyi-2900000000-5f34cefba25c54263b2a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-10-Hydroxy-8-decene-4,6-diynoic acid 40V, Negative-QTOF	splash10-029i-9300000000-e2000db9c39161856205	2021-09-23	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

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

FDB003056

KNApSAcK ID

Not Available

Chemspider ID

7822572

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9543622

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 (Z)-10-Hydroxy-8-decene-4,6-diynoic acid (HMDB0031055)

MOL for HMDB0031055 ((Z)-10-Hydroxy-8-decene-4,6-diynoic acid)

3D MOL for HMDB0031055 ((Z)-10-Hydroxy-8-decene-4,6-diynoic acid)

3D SDF for HMDB0031055 ((Z)-10-Hydroxy-8-decene-4,6-diynoic acid)

3D-SDF for HMDB0031055 ((Z)-10-Hydroxy-8-decene-4,6-diynoic acid)

PDB for HMDB0031055 ((Z)-10-Hydroxy-8-decene-4,6-diynoic acid)

3D PDB for HMDB0031055 ((Z)-10-Hydroxy-8-decene-4,6-diynoic acid)

SMILES for HMDB0031055 ((Z)-10-Hydroxy-8-decene-4,6-diynoic acid)

INCHI for HMDB0031055 ((Z)-10-Hydroxy-8-decene-4,6-diynoic acid)

Structure for HMDB0031055 ((Z)-10-Hydroxy-8-decene-4,6-diynoic acid)

3D Structure for HMDB0031055 ((Z)-10-Hydroxy-8-decene-4,6-diynoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra