Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:18:45 UTC
Update Date2022-03-07 02:56:00 UTC
HMDB IDHMDB0038966
Secondary Accession Numbers
  • HMDB38966
Metabolite Identification
Common Name(9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol
Description(9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol, also known as (9E)-11,16-dihydroxyoctadeca-9,17-dien-12,14-diyn-1-yl acetic acid, belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms. Based on a literature review a small amount of articles have been published on (9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol.
Structure
Data?1563863289
Synonyms
ValueSource
(9E)-11,16-Dihydroxyoctadeca-9,17-dien-12,14-diyn-1-yl acetic acidHMDB
Chemical FormulaC20H28O4
Average Molecular Weight332.4339
Monoisotopic Molecular Weight332.198759384
IUPAC Name(9E)-11,16-dihydroxyoctadeca-9,17-dien-12,14-diyn-1-yl acetate
Traditional Name(9E)-11,16-dihydroxyoctadeca-9,17-dien-12,14-diyn-1-yl acetate
CAS Registry Number52691-49-3
SMILES
CC(=O)OCCCCCCCC\C=C\C(O)C#CC#CC(O)C=C
InChI Identifier
InChI=1S/C20H28O4/c1-3-19(22)14-11-12-16-20(23)15-10-8-6-4-5-7-9-13-17-24-18(2)21/h3,10,15,19-20,22-23H,1,4-9,13,17H2,2H3/b15-10+
InChI KeyVVURZXYIXNNJCG-XNTDXEJSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentLong-chain fatty alcohols
Alternative Parents
Substituents
  • Long chain fatty alcohol
  • Fatty alcohol ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0076 g/LALOGPS
logP4.27ALOGPS
logP3.82ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)13.03ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity98.31 m³·mol⁻¹ChemAxon
Polarizability40.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+189.58631661259
DarkChem[M-H]-187.60931661259
DeepCCS[M+H]+178.96530932474
DeepCCS[M-H]-176.60730932474
DeepCCS[M-2H]-209.49430932474
DeepCCS[M+Na]+185.05830932474
AllCCS[M+H]+188.032859911
AllCCS[M+H-H2O]+185.132859911
AllCCS[M+NH4]+190.632859911
AllCCS[M+Na]+191.432859911
AllCCS[M-H]-184.832859911
AllCCS[M+Na-2H]-186.332859911
AllCCS[M+HCOO]-188.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diolCC(=O)OCCCCCCCC\C=C\C(O)C#CC#CC(O)C=C4166.2Standard polar33892256
(9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diolCC(=O)OCCCCCCCC\C=C\C(O)C#CC#CC(O)C=C2532.7Standard non polar33892256
(9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diolCC(=O)OCCCCCCCC\C=C\C(O)C#CC#CC(O)C=C2748.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol,1TMS,isomer #1C=CC(O)C#CC#CC(/C=C/CCCCCCCCOC(C)=O)O[Si](C)(C)C2645.2Semi standard non polar33892256
(9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol,1TMS,isomer #2C=CC(C#CC#CC(O)/C=C/CCCCCCCCOC(C)=O)O[Si](C)(C)C2626.0Semi standard non polar33892256
(9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol,2TMS,isomer #1C=CC(C#CC#CC(/C=C/CCCCCCCCOC(C)=O)O[Si](C)(C)C)O[Si](C)(C)C2702.2Semi standard non polar33892256
(9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol,1TBDMS,isomer #1C=CC(O)C#CC#CC(/C=C/CCCCCCCCOC(C)=O)O[Si](C)(C)C(C)(C)C2884.4Semi standard non polar33892256
(9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol,1TBDMS,isomer #2C=CC(C#CC#CC(O)/C=C/CCCCCCCCOC(C)=O)O[Si](C)(C)C(C)(C)C2865.9Semi standard non polar33892256
(9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol,2TBDMS,isomer #1C=CC(C#CC#CC(/C=C/CCCCCCCCOC(C)=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3138.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-06xx-7494000000-4a4628674e9f074e67b02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol GC-MS (2 TMS) - 70eV, Positivesplash10-0006-9214500000-431553ff3b4917b897652017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol 10V, Positive-QTOFsplash10-00lr-1139000000-ea00ffc1298ce835d5492016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol 20V, Positive-QTOFsplash10-05gi-2592000000-315683dce7d9466c58a02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol 40V, Positive-QTOFsplash10-0kbg-7980000000-4008a662f8cff52083812016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol 10V, Negative-QTOFsplash10-001i-5139000000-23fe5d79ac8f48f0a11b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol 20V, Negative-QTOFsplash10-0a4i-9112000000-0dc66fd9e96ac11e3a6c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol 40V, Negative-QTOFsplash10-0a4i-9010000000-09cc57eec7a2f0bea5432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol 10V, Negative-QTOFsplash10-053r-4009000000-726e81124985954871b02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol 20V, Negative-QTOFsplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol 40V, Negative-QTOFsplash10-0a4i-9020000000-1f2d9ffacf2abb6b492c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol 10V, Positive-QTOFsplash10-014i-1398000000-eaa98b65071e50a5f2c42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol 20V, Positive-QTOFsplash10-0axv-2091000000-45663eed686de4d4ec4b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9Z,11S,16S)-1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol 40V, Positive-QTOFsplash10-00nr-1970000000-b36edf3f03e0042ab00d2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB018452
KNApSAcK IDNot Available
Chemspider ID29365067
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71307305
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.