Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-14 02:27:54 UTC
Update Date2022-03-07 02:49:21 UTC
HMDB IDHMDB0004710
Secondary Accession Numbers
  • HMDB04710
Metabolite Identification
Common Name9,10,13-TriHOME
Description9,10,13-TriHOME belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, 9,10,13-trihome is considered to be an octadecanoid. Based on a literature review a significant number of articles have been published on 9,10,13-TriHOME.
Structure
Data?1582752313
Synonyms
ValueSource
(11E)-9,10,13-Trihydroxyoctadec-11-enoateHMDB
(11E)-9,10,13-Trihydroxyoctadec-11-enoic acidHMDB
(e)-9,10,13-Trihydroxy-11-octadecenoateHMDB
(e)-9,10,13-Trihydroxy-11-octadecenoic acidHMDB
9,10,13-Trihydroxy-11-octadecenoateHMDB
9,10,13-Trihydroxy-11-octadecenoic acidHMDB
9,10,13-Trihydroxyoctadec-11-enoateHMDB
9,10,13-Trihydroxyoctadec-11-enoic acidHMDB, MeSH
(9S,10R,11E,13S)-9,10,13-Trihydroxyoctadec-11-enoateGenerator, HMDB
Chemical FormulaC18H34O5
Average Molecular Weight330.4596
Monoisotopic Molecular Weight330.240624198
IUPAC Name(9S,10R,11E,13S)-9,10,13-trihydroxyoctadec-11-enoic acid
Traditional Name(9S,10R,11E,13S)-9,10,13-trihydroxyoctadec-11-enoic acid
CAS Registry Number29907-57-1
SMILES
CCCCC[C@H](O)\C=C\[C@@H](O)[C@@H](O)CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H34O5/c1-2-3-7-10-15(19)13-14-17(21)16(20)11-8-5-4-6-9-12-18(22)23/h13-17,19-21H,2-12H2,1H3,(H,22,23)/b14-13+/t15-,16-,17+/m0/s1
InChI KeyNTVFQBIHLSPEGQ-SYMVGPSASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • 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
StateSolid
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 Solubility0.15 g/LALOGPS
logP3.76ALOGPS
logP3.25ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity91.79 m³·mol⁻¹ChemAxon
Polarizability39.1 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]+183.99331661259
DarkChem[M-H]-185.7231661259
DeepCCS[M+H]+190.45230932474
DeepCCS[M-H]-188.05630932474
DeepCCS[M-2H]-221.75730932474
DeepCCS[M+Na]+196.92830932474
AllCCS[M+H]+190.232859911
AllCCS[M+H-H2O]+187.432859911
AllCCS[M+NH4]+192.732859911
AllCCS[M+Na]+193.432859911
AllCCS[M-H]-184.532859911
AllCCS[M+Na-2H]-185.832859911
AllCCS[M+HCOO]-187.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
9,10,13-TriHOMECCCCC[C@H](O)\C=C\[C@@H](O)[C@@H](O)CCCCCCCC(O)=O4272.0Standard polar33892256
9,10,13-TriHOMECCCCC[C@H](O)\C=C\[C@@H](O)[C@@H](O)CCCCCCCC(O)=O2548.3Standard non polar33892256
9,10,13-TriHOMECCCCC[C@H](O)\C=C\[C@@H](O)[C@@H](O)CCCCCCCC(O)=O2704.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
9,10,13-TriHOME,1TMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](O)[C@@H](O)CCCCCCCC(=O)O)O[Si](C)(C)C2757.0Semi standard non polar33892256
9,10,13-TriHOME,1TMS,isomer #2CCCCC[C@H](O)/C=C/[C@@H](O[Si](C)(C)C)[C@@H](O)CCCCCCCC(=O)O2685.4Semi standard non polar33892256
9,10,13-TriHOME,1TMS,isomer #3CCCCC[C@H](O)/C=C/[C@@H](O)[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C2675.5Semi standard non polar33892256
9,10,13-TriHOME,1TMS,isomer #4CCCCC[C@H](O)/C=C/[C@@H](O)[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C2692.0Semi standard non polar33892256
9,10,13-TriHOME,2TMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](O[Si](C)(C)C)[C@@H](O)CCCCCCCC(=O)O)O[Si](C)(C)C2700.4Semi standard non polar33892256
9,10,13-TriHOME,2TMS,isomer #2CCCCC[C@@H](/C=C/[C@@H](O)[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C2706.4Semi standard non polar33892256
9,10,13-TriHOME,2TMS,isomer #3CCCCC[C@@H](/C=C/[C@@H](O)[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2733.0Semi standard non polar33892256
9,10,13-TriHOME,2TMS,isomer #4CCCCC[C@H](O)/C=C/[C@@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C2702.7Semi standard non polar33892256
9,10,13-TriHOME,2TMS,isomer #5CCCCC[C@H](O)/C=C/[C@@H](O[Si](C)(C)C)[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C2683.9Semi standard non polar33892256
9,10,13-TriHOME,2TMS,isomer #6CCCCC[C@H](O)/C=C/[C@@H](O)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2673.2Semi standard non polar33892256
9,10,13-TriHOME,3TMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C2711.3Semi standard non polar33892256
9,10,13-TriHOME,3TMS,isomer #2CCCCC[C@@H](/C=C/[C@@H](O[Si](C)(C)C)[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2738.7Semi standard non polar33892256
9,10,13-TriHOME,3TMS,isomer #3CCCCC[C@@H](/C=C/[C@@H](O)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2742.2Semi standard non polar33892256
9,10,13-TriHOME,3TMS,isomer #4CCCCC[C@H](O)/C=C/[C@@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2710.9Semi standard non polar33892256
9,10,13-TriHOME,4TMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2718.1Semi standard non polar33892256
9,10,13-TriHOME,1TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](O)[C@@H](O)CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2978.5Semi standard non polar33892256
9,10,13-TriHOME,1TBDMS,isomer #2CCCCC[C@H](O)/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCCCCCC(=O)O2920.2Semi standard non polar33892256
9,10,13-TriHOME,1TBDMS,isomer #3CCCCC[C@H](O)/C=C/[C@@H](O)[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2928.2Semi standard non polar33892256
9,10,13-TriHOME,1TBDMS,isomer #4CCCCC[C@H](O)/C=C/[C@@H](O)[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2944.8Semi standard non polar33892256
9,10,13-TriHOME,2TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C3188.4Semi standard non polar33892256
9,10,13-TriHOME,2TBDMS,isomer #2CCCCC[C@@H](/C=C/[C@@H](O)[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3209.9Semi standard non polar33892256
9,10,13-TriHOME,2TBDMS,isomer #3CCCCC[C@@H](/C=C/[C@@H](O)[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3229.2Semi standard non polar33892256
9,10,13-TriHOME,2TBDMS,isomer #4CCCCC[C@H](O)/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C3192.6Semi standard non polar33892256
9,10,13-TriHOME,2TBDMS,isomer #5CCCCC[C@H](O)/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C3193.6Semi standard non polar33892256
9,10,13-TriHOME,2TBDMS,isomer #6CCCCC[C@H](O)/C=C/[C@@H](O)[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3190.2Semi standard non polar33892256
9,10,13-TriHOME,3TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3473.5Semi standard non polar33892256
9,10,13-TriHOME,3TBDMS,isomer #2CCCCC[C@@H](/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3476.7Semi standard non polar33892256
9,10,13-TriHOME,3TBDMS,isomer #3CCCCC[C@@H](/C=C/[C@@H](O)[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3486.1Semi standard non polar33892256
9,10,13-TriHOME,3TBDMS,isomer #4CCCCC[C@H](O)/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3459.1Semi standard non polar33892256
9,10,13-TriHOME,4TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3691.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 9,10,13-TriHOME GC-MS (Non-derivatized) - 70eV, Positivesplash10-01w0-8912000000-5a1e2b5948d62d3d2a8a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9,10,13-TriHOME GC-MS (4 TMS) - 70eV, Positivesplash10-0ufr-9213245000-c56c2b31482e1a9756192017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9,10,13-TriHOME 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 - 9,10,13-TriHOME 10V, Positive-QTOFsplash10-03dj-0169000000-7c5aaa7b03ba201209182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9,10,13-TriHOME 20V, Positive-QTOFsplash10-002b-5942000000-a07971b592bb673ce4152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9,10,13-TriHOME 40V, Positive-QTOFsplash10-05pp-9310000000-58283bb52ee9feb9d63d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9,10,13-TriHOME 10V, Negative-QTOFsplash10-004i-0019000000-f4a3d38dc4bb1c275bcc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9,10,13-TriHOME 20V, Negative-QTOFsplash10-08i0-1935000000-3f4e473193cf8a188ff62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9,10,13-TriHOME 40V, Negative-QTOFsplash10-0a4i-8900000000-b2d3152f1de8d749a99a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9,10,13-TriHOME 10V, Positive-QTOFsplash10-03dj-1279000000-6f96d792b4e00d659f6b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9,10,13-TriHOME 20V, Positive-QTOFsplash10-0002-7953000000-6566bcdbde83ae6f27782021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9,10,13-TriHOME 40V, Positive-QTOFsplash10-0api-9200000000-24a2bc2c01a5f3e1a97e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9,10,13-TriHOME 10V, Negative-QTOFsplash10-004i-0009000000-e02991afc43a2235e25f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9,10,13-TriHOME 20V, Negative-QTOFsplash10-004i-1649000000-db07237f7f737ccb656a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9,10,13-TriHOME 40V, Negative-QTOFsplash10-0a4i-9851000000-9fd4ae86fed46710873d2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000513 +/- 0.000083 (0.000430 - 0.000596) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000513 +/- 0.000083 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00116 +/- 0.00064 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00033 +/- 0.00018 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023419
KNApSAcK IDNot Available
Chemspider ID30776564
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14968868
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.