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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:06:04 UTC
Update Date2022-03-07 02:54:03 UTC
HMDB IDHMDB0034295
Secondary Accession Numbers
  • HMDB34295
Metabolite Identification
Common NameFloionolic acid
DescriptionFloionolic acid, also known as floionolate, 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. Based on a literature review a significant number of articles have been published on Floionolic acid.
Structure
Data?1563862541
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 Weight332.4754
Monoisotopic Molecular Weight332.256274262
IUPAC Name9,10,18-trihydroxyoctadecanoic acid
Traditional Namephloionolic acid
CAS Registry Number17705-68-9
SMILES
OCCCCCCCCC(O)C(O)CCCCCCCC(O)=O
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point104 - 105 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
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]+183.40331661259
DarkChem[M-H]-182.83631661259
DeepCCS[M+H]+185.4630932474
DeepCCS[M-H]-182.9130932474
DeepCCS[M-2H]-217.77230932474
DeepCCS[M+Na]+194.06330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Floionolic acidOCCCCCCCCC(O)C(O)CCCCCCCC(O)=O4186.9Standard polar33892256
Floionolic acidOCCCCCCCCC(O)C(O)CCCCCCCC(O)=O2533.2Standard non polar33892256
Floionolic acidOCCCCCCCCC(O)C(O)CCCCCCCC(O)=O2805.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Floionolic acid,1TMS,isomer #1C[Si](C)(C)OCCCCCCCCC(O)C(O)CCCCCCCC(=O)O2895.4Semi standard non polar33892256
Floionolic acid,1TMS,isomer #2C[Si](C)(C)OC(CCCCCCCCO)C(O)CCCCCCCC(=O)O2840.4Semi standard non polar33892256
Floionolic acid,1TMS,isomer #3C[Si](C)(C)OC(CCCCCCCC(=O)O)C(O)CCCCCCCCO2841.5Semi standard non polar33892256
Floionolic acid,1TMS,isomer #4C[Si](C)(C)OC(=O)CCCCCCCC(O)C(O)CCCCCCCCO2867.2Semi standard non polar33892256
Floionolic acid,2TMS,isomer #1C[Si](C)(C)OCCCCCCCCC(O[Si](C)(C)C)C(O)CCCCCCCC(=O)O2881.9Semi standard non polar33892256
Floionolic acid,2TMS,isomer #2C[Si](C)(C)OCCCCCCCCC(O)C(CCCCCCCC(=O)O)O[Si](C)(C)C2883.3Semi standard non polar33892256
Floionolic acid,2TMS,isomer #3C[Si](C)(C)OCCCCCCCCC(O)C(O)CCCCCCCC(=O)O[Si](C)(C)C2954.4Semi standard non polar33892256
Floionolic acid,2TMS,isomer #4C[Si](C)(C)OC(CCCCCCCCO)C(CCCCCCCC(=O)O)O[Si](C)(C)C2868.9Semi standard non polar33892256
Floionolic acid,2TMS,isomer #5C[Si](C)(C)OC(=O)CCCCCCCC(O)C(CCCCCCCCO)O[Si](C)(C)C2846.3Semi standard non polar33892256
Floionolic acid,2TMS,isomer #6C[Si](C)(C)OC(=O)CCCCCCCC(O[Si](C)(C)C)C(O)CCCCCCCCO2846.5Semi standard non polar33892256
Floionolic acid,3TMS,isomer #1C[Si](C)(C)OCCCCCCCCC(O[Si](C)(C)C)C(CCCCCCCC(=O)O)O[Si](C)(C)C2850.0Semi standard non polar33892256
Floionolic acid,3TMS,isomer #2C[Si](C)(C)OCCCCCCCCC(O[Si](C)(C)C)C(O)CCCCCCCC(=O)O[Si](C)(C)C2883.0Semi standard non polar33892256
Floionolic acid,3TMS,isomer #3C[Si](C)(C)OCCCCCCCCC(O)C(CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2883.7Semi standard non polar33892256
Floionolic acid,3TMS,isomer #4C[Si](C)(C)OC(=O)CCCCCCCC(O[Si](C)(C)C)C(CCCCCCCCO)O[Si](C)(C)C2816.0Semi standard non polar33892256
Floionolic acid,4TMS,isomer #1C[Si](C)(C)OCCCCCCCCC(O[Si](C)(C)C)C(CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2831.0Semi standard non polar33892256
Floionolic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCCCCCC(O)C(O)CCCCCCCC(=O)O3133.1Semi standard non polar33892256
Floionolic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(CCCCCCCCO)C(O)CCCCCCCC(=O)O3094.1Semi standard non polar33892256
Floionolic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(CCCCCCCC(=O)O)C(O)CCCCCCCCO3094.7Semi standard non polar33892256
Floionolic acid,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(O)C(O)CCCCCCCCO3104.1Semi standard non polar33892256
Floionolic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(O)CCCCCCCC(=O)O3385.4Semi standard non polar33892256
Floionolic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCCCCCCCCC(O)C(CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C3386.7Semi standard non polar33892256
Floionolic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OCCCCCCCCC(O)C(O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C3406.0Semi standard non polar33892256
Floionolic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(CCCCCCCCO)C(CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C3378.7Semi standard non polar33892256
Floionolic acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(O)C(CCCCCCCCO)O[Si](C)(C)C(C)(C)C3336.7Semi standard non polar33892256
Floionolic acid,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(O[Si](C)(C)C(C)(C)C)C(O)CCCCCCCCO3337.3Semi standard non polar33892256
Floionolic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C3614.5Semi standard non polar33892256
Floionolic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C3590.9Semi standard non polar33892256
Floionolic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OCCCCCCCCC(O)C(CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3590.9Semi standard non polar33892256
Floionolic acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(O[Si](C)(C)C(C)(C)C)C(CCCCCCCCO)O[Si](C)(C)C(C)(C)C3550.3Semi standard non polar33892256
Floionolic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3752.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Floionolic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-1911000000-d840e20ff525bafe39b42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Floionolic acid GC-MS (4 TMS) - 70eV, Positivesplash10-0a4i-9808748000-381c45839b6ccd5dcd802017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Floionolic acid 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 - Floionolic acid 10V, Positive-QTOFsplash10-014j-0159000000-03c0b5a582f0608854bd2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 20V, Positive-QTOFsplash10-00mk-4952000000-5b68b9c79eff7efcc8b32015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 40V, Positive-QTOFsplash10-05ne-9410000000-7015b14a06ff39c543502015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 10V, Positive-QTOFsplash10-014j-0159000000-03c0b5a582f0608854bd2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 20V, Positive-QTOFsplash10-00mk-4952000000-5b68b9c79eff7efcc8b32015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 40V, Positive-QTOFsplash10-05ne-9410000000-7015b14a06ff39c543502015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 10V, Positive-QTOFsplash10-014j-0159000000-03c0b5a582f0608854bd2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 20V, Positive-QTOFsplash10-00mk-4952000000-5b68b9c79eff7efcc8b32015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 40V, Positive-QTOFsplash10-05ne-9410000000-7015b14a06ff39c543502015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 10V, Positive-QTOFsplash10-014j-0159000000-03c0b5a582f0608854bd2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 20V, Positive-QTOFsplash10-00mk-4952000000-5b68b9c79eff7efcc8b32015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 40V, Positive-QTOFsplash10-05ne-9410000000-7015b14a06ff39c543502015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 10V, Positive-QTOFsplash10-014j-0159000000-03c0b5a582f0608854bd2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 20V, Positive-QTOFsplash10-00mk-4952000000-5b68b9c79eff7efcc8b32015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 40V, Positive-QTOFsplash10-05ne-9410000000-7015b14a06ff39c543502015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 10V, Negative-QTOFsplash10-001i-0129000000-b1d85f203fcb931fa03a2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 20V, Negative-QTOFsplash10-08gi-1946000000-02d24ec6ae833a1fa1762015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 40V, Negative-QTOFsplash10-0a4i-7900000000-f5b7a54f8cc1c84bc4392015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 10V, Negative-QTOFsplash10-001i-0129000000-b1d85f203fcb931fa03a2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 20V, Negative-QTOFsplash10-08gi-1946000000-02d24ec6ae833a1fa1762015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 40V, Negative-QTOFsplash10-0a4i-7900000000-f5b7a54f8cc1c84bc4392015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 10V, Negative-QTOFsplash10-001i-0129000000-b1d85f203fcb931fa03a2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 20V, Negative-QTOFsplash10-08gi-1946000000-02d24ec6ae833a1fa1762015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 40V, Negative-QTOFsplash10-0a4i-7900000000-f5b7a54f8cc1c84bc4392015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Floionolic acid 10V, Negative-QTOFsplash10-001i-0129000000-b1d85f203fcb931fa03a2015-05-27Wishart 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 IDFDB012635
KNApSAcK IDC00034431
Chemspider ID4446065
KEGG Compound IDC19621
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5282938
PDB IDNot Available
ChEBI ID133325
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.