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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2014-04-11 22:17:06 UTC
Update Date2021-09-14 14:58:38 UTC
HMDB IDHMDB0061657
Secondary Accession Numbers
  • HMDB61657
Metabolite Identification
Common Name3-hydroxypentadecanoic acid
Description3-hydroxypentadecanoic acid 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. 3-hydroxypentadecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866216
Synonyms
ValueSource
3-HydroxypentadecanoateGenerator
3-Hydroxy-pentadecanoateGenerator
Chemical FormulaC15H30O3
Average Molecular Weight258.3969
Monoisotopic Molecular Weight258.219494826
IUPAC Name3-hydroxypentadecanoic acid
Traditional Name3-hydroxypentadecanoic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCC(O)CC(O)=O
InChI Identifier
InChI=1S/C15H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-14(16)13-15(17)18/h14,16H,2-13H2,1H3,(H,17,18)
InChI KeyATMSEJBABXCWDW-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
  • Beta-hydroxy acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Hydroxy fatty acid
  • Hydroxy acid
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
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 Solubility0.013 g/LALOGPS
logP5.13ALOGPS
logP4.58ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.67ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity74 m³·mol⁻¹ChemAxon
Polarizability32.98 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]+166.3531661259
DarkChem[M-H]-164.84931661259
DeepCCS[M+H]+166.15430932474
DeepCCS[M-H]-162.13330932474
DeepCCS[M-2H]-199.33430932474
DeepCCS[M+Na]+175.19430932474
AllCCS[M+H]+170.932859911
AllCCS[M+H-H2O]+167.732859911
AllCCS[M+NH4]+173.932859911
AllCCS[M+Na]+174.732859911
AllCCS[M-H]-169.232859911
AllCCS[M+Na-2H]-170.232859911
AllCCS[M+HCOO]-171.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-hydroxypentadecanoic acidCCCCCCCCCCCCC(O)CC(O)=O3263.8Standard polar33892256
3-hydroxypentadecanoic acidCCCCCCCCCCCCC(O)CC(O)=O1919.1Standard non polar33892256
3-hydroxypentadecanoic acidCCCCCCCCCCCCC(O)CC(O)=O2051.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-hydroxypentadecanoic acid,1TMS,isomer #1CCCCCCCCCCCCC(CC(=O)O)O[Si](C)(C)C2092.4Semi standard non polar33892256
3-hydroxypentadecanoic acid,1TMS,isomer #2CCCCCCCCCCCCC(O)CC(=O)O[Si](C)(C)C2089.1Semi standard non polar33892256
3-hydroxypentadecanoic acid,2TMS,isomer #1CCCCCCCCCCCCC(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2129.0Semi standard non polar33892256
3-hydroxypentadecanoic acid,1TBDMS,isomer #1CCCCCCCCCCCCC(CC(=O)O)O[Si](C)(C)C(C)(C)C2329.5Semi standard non polar33892256
3-hydroxypentadecanoic acid,1TBDMS,isomer #2CCCCCCCCCCCCC(O)CC(=O)O[Si](C)(C)C(C)(C)C2335.0Semi standard non polar33892256
3-hydroxypentadecanoic acid,2TBDMS,isomer #1CCCCCCCCCCCCC(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2587.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-hydroxypentadecanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9420000000-7cb83381afd7477ceb3f2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-hydroxypentadecanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9233000000-fae458e97af8bcc0aa892017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-hydroxypentadecanoic 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 - 3-hydroxypentadecanoic acid 10V, Positive-QTOFsplash10-0006-0190000000-7a2afe92f91abccfd6f42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxypentadecanoic acid 20V, Positive-QTOFsplash10-006y-5980000000-9f678f922af27ad567202017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxypentadecanoic acid 40V, Positive-QTOFsplash10-052f-9600000000-7582c195956a0927f1f92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxypentadecanoic acid 10V, Negative-QTOFsplash10-0a4i-0090000000-645f9c2c220ffc7405392017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxypentadecanoic acid 20V, Negative-QTOFsplash10-0btj-3390000000-abc9b4fae3e43d04483b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxypentadecanoic acid 40V, Negative-QTOFsplash10-0a4m-9520000000-742c1c4476e166b11d1c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxypentadecanoic acid 10V, Positive-QTOFsplash10-0a4i-4390000000-14b7bcd2fe2a3f4fe7932021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxypentadecanoic acid 20V, Positive-QTOFsplash10-0a4j-9200000000-f2ce46ce8ad4c34db5872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxypentadecanoic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-c8463e5c329428499b102021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxypentadecanoic acid 10V, Negative-QTOFsplash10-0a4i-7090000000-7a1e1069b1654d7cd0cd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxypentadecanoic acid 20V, Negative-QTOFsplash10-0a4i-9000000000-928fa01e87973b2ef24d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxypentadecanoic acid 40V, Negative-QTOFsplash10-0006-9000000000-b4af13c76abafd9bd5812021-09-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound182089
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.
  6. The AOCS Lipid Library [Link]