9,10,18-Trihydroxyoctadecanoic acid (CHEM028355)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:23:54 UTC
Update Date2016-11-09 01:18:40 UTC
Accession NumberCHEM028355
Identification
Common Name9,10,18-Trihydroxyoctadecanoic acid
ClassSmall Molecule
DescriptionAn omega-hydroxy fatty acid that is 18-hydroxyoctadecanoic acid carrying two additional hydroxy substituents at positions 9 and 10.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
9,10,18-Trihydroxy-octadecanoic acidChEBI
9,10,18-Trihydroxystearic acidChEBI
9,10,18-Trihydroxy-octadecanoateGenerator
9,10,18-TrihydroxystearateGenerator
FloionolateGenerator
Phloionolic acidHMDB
PhloionolateHMDB
9,10,18-TrihydroxyoctadecanoateHMDB
Chemical FormulaC18H36O5
Average Molecular Mass332.475 g/mol
Monoisotopic Mass332.256 g/mol
CAS Registry Number496-86-6
IUPAC Name9,10,18-trihydroxyoctadecanoic acid
Traditional Namephloionolic acid
SMILESOCCCCCCCCC(O)C(O)CCCCCCCC(O)=O
InChI IdentifierInChI=1S/C18H36O5/c19-15-11-7-2-1-4-8-12-16(20)17(21)13-9-5-3-6-10-14-18(22)23/h16-17,19-21H,1-15H2,(H,22,23)
InChI KeyOISFHODBOQNZAG-UHFFFAOYSA-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
  • Secondary alcohol
  • Polyol
  • 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 FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP3.63ALOGPS
logP3.25ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity91.25 m³·mol⁻¹ChemAxon
Polarizability41.24 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-1911000000-d840e20ff525bafe39b4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0a4i-9808748000-381c45839b6ccd5dcd80Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0159000000-03c0b5a582f0608854bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00mk-4952000000-5b68b9c79eff7efcc8b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ne-9410000000-7015b14a06ff39c54350Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0159000000-03c0b5a582f0608854bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00mk-4952000000-5b68b9c79eff7efcc8b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ne-9410000000-7015b14a06ff39c54350Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0159000000-03c0b5a582f0608854bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00mk-4952000000-5b68b9c79eff7efcc8b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ne-9410000000-7015b14a06ff39c54350Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0159000000-03c0b5a582f0608854bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00mk-4952000000-5b68b9c79eff7efcc8b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ne-9410000000-7015b14a06ff39c54350Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0159000000-03c0b5a582f0608854bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00mk-4952000000-5b68b9c79eff7efcc8b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ne-9410000000-7015b14a06ff39c54350Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0129000000-b1d85f203fcb931fa03aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08gi-1946000000-02d24ec6ae833a1fa176Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-f5b7a54f8cc1c84bc439Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0129000000-b1d85f203fcb931fa03aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08gi-1946000000-02d24ec6ae833a1fa176Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-f5b7a54f8cc1c84bc439Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0129000000-b1d85f203fcb931fa03aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08gi-1946000000-02d24ec6ae833a1fa176Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-f5b7a54f8cc1c84bc439Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0129000000-b1d85f203fcb931fa03aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0034295
FooDB IDFDB012635
Phenol Explorer IDNot Available
KNApSAcK IDC00034431
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4446065
ChEBI ID133325
PubChem Compound ID5282938
Kegg Compound IDC19621
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11171237
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1567426
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16417304
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17328933
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18998700
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23384782
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=240326
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24086493
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24197199
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24221429
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=4356240
12. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
13. 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.
14. 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.
15. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
16. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
17. The lipid handbook with CD-ROM