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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:50:57 UTC
Update Date2022-03-07 02:56:11 UTC
HMDB IDHMDB0039403
Secondary Accession Numbers
  • HMDB39403
Metabolite Identification
Common Name2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate
Description2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate 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 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate.
Structure
Data?1563863369
Synonyms
ValueSource
2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetic acidGenerator
(5E,12Z)-2-Hydroxy-4-oxohenicosa-5,12-dien-1-yl acetic acidHMDB
Chemical FormulaC23H40O4
Average Molecular Weight380.5613
Monoisotopic Molecular Weight380.292659768
IUPAC Name(5E,12Z)-2-hydroxy-4-oxohenicosa-5,12-dien-1-yl acetate
Traditional Name(5E,12Z)-2-hydroxy-4-oxohenicosa-5,12-dien-1-yl acetate
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCC\C=C\C(=O)CC(O)COC(C)=O
InChI Identifier
InChI=1S/C23H40O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-22(25)19-23(26)20-27-21(2)24/h10-11,17-18,23,26H,3-9,12-16,19-20H2,1-2H3/b11-10-,18-17+
InChI KeyRCVPNKIEBGIOFR-APUJEFNWSA-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
  • B'-hydroxy-alpha,beta-unsaturated-ketone
  • Beta-hydroxy ketone
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Carboxylic acid ester
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • 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 Solubility0.00029 g/LALOGPS
logP6.51ALOGPS
logP6.34ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)14.25ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity113.56 m³·mol⁻¹ChemAxon
Polarizability46.91 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+206.00630932474
DeepCCS[M-H]-203.45530932474
DeepCCS[M-2H]-236.65830932474
DeepCCS[M+Na]+212.61130932474
AllCCS[M+H]+204.632859911
AllCCS[M+H-H2O]+202.232859911
AllCCS[M+NH4]+206.832859911
AllCCS[M+Na]+207.432859911
AllCCS[M-H]-199.932859911
AllCCS[M+Na-2H]-202.532859911
AllCCS[M+HCOO]-205.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetateCCCCCCCC\C=C/CCCCC\C=C\C(=O)CC(O)COC(C)=O3604.4Standard polar33892256
2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetateCCCCCCCC\C=C/CCCCC\C=C\C(=O)CC(O)COC(C)=O2634.3Standard non polar33892256
2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetateCCCCCCCC\C=C/CCCCC\C=C\C(=O)CC(O)COC(C)=O2841.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate,1TMS,isomer #1CCCCCCCC/C=C\CCCCC/C=C/C(=O)CC(COC(C)=O)O[Si](C)(C)C2843.3Semi standard non polar33892256
2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate,1TMS,isomer #2CCCCCCCC/C=C\CCCCC/C=C/C(=CC(O)COC(C)=O)O[Si](C)(C)C2983.2Semi standard non polar33892256
2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate,2TMS,isomer #1CCCCCCCC/C=C\CCCCC/C=C/C(=CC(COC(C)=O)O[Si](C)(C)C)O[Si](C)(C)C3003.9Semi standard non polar33892256
2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate,2TMS,isomer #1CCCCCCCC/C=C\CCCCC/C=C/C(=CC(COC(C)=O)O[Si](C)(C)C)O[Si](C)(C)C2846.4Standard non polar33892256
2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate,1TBDMS,isomer #1CCCCCCCC/C=C\CCCCC/C=C/C(=O)CC(COC(C)=O)O[Si](C)(C)C(C)(C)C3091.6Semi standard non polar33892256
2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate,1TBDMS,isomer #2CCCCCCCC/C=C\CCCCC/C=C/C(=CC(O)COC(C)=O)O[Si](C)(C)C(C)(C)C3223.0Semi standard non polar33892256
2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate,2TBDMS,isomer #1CCCCCCCC/C=C\CCCCC/C=C/C(=CC(COC(C)=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3479.6Semi standard non polar33892256
2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate,2TBDMS,isomer #1CCCCCCCC/C=C\CCCCC/C=C/C(=CC(COC(C)=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3189.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-01vo-9555000000-5acfd0ddec55c577f48f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate GC-MS (1 TMS) - 70eV, Positivesplash10-002f-9222000000-f0f5fb1c4610e37791ab2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate 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 - 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate 10V, Positive-QTOFsplash10-03e9-1029000000-c32a0e6d54e243d27e9c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate 20V, Positive-QTOFsplash10-0w90-2389000000-e67de976acf181197c3c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate 40V, Positive-QTOFsplash10-01ox-7491000000-57a0a2d519cda31b2f042016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate 10V, Negative-QTOFsplash10-056r-9137000000-0de3d0020e21ea1bf1202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate 20V, Negative-QTOFsplash10-0a4i-9122000000-41b046e84c8654a1b7ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate 40V, Negative-QTOFsplash10-0a4i-9010000000-1070d2025e8a88e28b1a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate 10V, Positive-QTOFsplash10-01q9-1129000000-df8ce7625d83c8e9411c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate 20V, Positive-QTOFsplash10-0ha3-6629000000-cb53f72ce6810fbea0e92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate 40V, Positive-QTOFsplash10-052e-9400000000-675b97b5bb802afdf8f32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate 10V, Negative-QTOFsplash10-0a6r-3109000000-129d8f3fdf20cf40c7542021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate 20V, Negative-QTOFsplash10-0a4i-9016000000-49f0ed14ea16e009de282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxo-5,12-heneicosadien-1-yl acetate 40V, Negative-QTOFsplash10-0a4i-9121000000-40554f0aef2c0c853c322021-09-24Wishart 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 IDFDB018978
KNApSAcK IDNot Available
Chemspider ID8301959
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10126440
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.