Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 04:25:48 UTC
Update Date2022-03-07 03:17:56 UTC
HMDB IDHMDB0062566
Secondary Accession Numbers
  • HMDB62566
Metabolite Identification
Common Name3-hydroxyicosanoic Acid
Description3-hydroxyicosanoic Acid, also known as 3-hydroxyeicosanoate or 3-hydroxyarachidic 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. Thus, 3-hydroxyicosanoic Acid is considered to be a fatty acid lipid molecule. 3-hydroxyicosanoic Acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866330
Synonyms
ValueSource
3-Hydroxyarachidic acidChEBI
3-Hydroxyeicosanoic acidChEBI
beta-Hydroxyachidic acidChEBI
beta-Hydroxyeicosanoic acidChEBI
beta-Hydroxyicosanoic acidChEBI
3-HydroxyarachidateGenerator
3-HydroxyeicosanoateGenerator
b-HydroxyachidateGenerator
b-Hydroxyachidic acidGenerator
beta-HydroxyachidateGenerator
Β-hydroxyachidateGenerator
Β-hydroxyachidic acidGenerator
b-HydroxyeicosanoateGenerator
b-Hydroxyeicosanoic acidGenerator
beta-HydroxyeicosanoateGenerator
Β-hydroxyeicosanoateGenerator
Β-hydroxyeicosanoic acidGenerator
b-HydroxyicosanoateGenerator
b-Hydroxyicosanoic acidGenerator
beta-HydroxyicosanoateGenerator
Β-hydroxyicosanoateGenerator
Β-hydroxyicosanoic acidGenerator
3-HydroxyicosanoateGenerator
Chemical FormulaC20H40O3
Average Molecular Weight328.537
Monoisotopic Molecular Weight328.297745148
IUPAC Name3-hydroxyicosanoic acid
Traditional Name3-hydroxyeicosanoic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(O)CC(O)=O
InChI Identifier
InChI=1S/C20H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(21)18-20(22)23/h19,21H,2-18H2,1H3,(H,22,23)
InChI KeyXXKHCFPQYSMGCI-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
  • Beta-hydroxy acid
  • Hydroxy acid
  • Secondary alcohol
  • 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 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 Solubility0.00049 g/lALOGPS
LogP7.69ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP7.69ALOGPS
logP6.8ChemAxon
logS-5.8ALOGPS
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 Count18ChemAxon
Refractivity97 m³·mol⁻¹ChemAxon
Polarizability43.44 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
DarkChem[M+H]+186.85531661259
DarkChem[M-H]-186.05131661259
DeepCCS[M+H]+183.91630932474
DeepCCS[M-H]-179.89630932474
DeepCCS[M-2H]-216.81430932474
DeepCCS[M+Na]+192.84330932474
AllCCS[M+H]+196.132859911
AllCCS[M+H-H2O]+193.532859911
AllCCS[M+NH4]+198.632859911
AllCCS[M+Na]+199.332859911
AllCCS[M-H]-188.132859911
AllCCS[M+Na-2H]-189.632859911
AllCCS[M+HCOO]-191.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-hydroxyicosanoic AcidCCCCCCCCCCCCCCCCCC(O)CC(O)=O3749.5Standard polar33892256
3-hydroxyicosanoic AcidCCCCCCCCCCCCCCCCCC(O)CC(O)=O2369.5Standard non polar33892256
3-hydroxyicosanoic AcidCCCCCCCCCCCCCCCCCC(O)CC(O)=O2548.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-hydroxyicosanoic Acid,1TMS,isomer #1CCCCCCCCCCCCCCCCCC(CC(=O)O)O[Si](C)(C)C2587.6Semi standard non polar33892256
3-hydroxyicosanoic Acid,1TMS,isomer #2CCCCCCCCCCCCCCCCCC(O)CC(=O)O[Si](C)(C)C2592.2Semi standard non polar33892256
3-hydroxyicosanoic Acid,2TMS,isomer #1CCCCCCCCCCCCCCCCCC(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2613.7Semi standard non polar33892256
3-hydroxyicosanoic Acid,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCC(CC(=O)O)O[Si](C)(C)C(C)(C)C2845.9Semi standard non polar33892256
3-hydroxyicosanoic Acid,1TBDMS,isomer #2CCCCCCCCCCCCCCCCCC(O)CC(=O)O[Si](C)(C)C(C)(C)C2846.9Semi standard non polar33892256
3-hydroxyicosanoic Acid,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCC(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3104.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-hydroxyicosanoic Acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8591000000-7c0e3bce2074cd9f44a02017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-hydroxyicosanoic Acid GC-MS (2 TMS) - 70eV, Positivesplash10-0adl-9323100000-b4f0900b618498979ae52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-hydroxyicosanoic 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-hydroxyicosanoic Acid 10V, Positive-QTOFsplash10-03di-0059000000-e936c41a541b1540339d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 20V, Positive-QTOFsplash10-02vl-1193000000-5fa84dc3a4c4f13c217a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 40V, Positive-QTOFsplash10-052o-6690000000-08e36015aa3a28f49e5c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 10V, Negative-QTOFsplash10-056r-0039000000-0af44605508babc943902017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 20V, Negative-QTOFsplash10-0api-3097000000-4b46f0aef956a1b66e602017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 40V, Negative-QTOFsplash10-0aou-9060000000-62e5ae5b33515cbd8fcc2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 10V, Positive-QTOFsplash10-004i-2039000000-60db8ad7748a61608b912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 20V, Positive-QTOFsplash10-0c2c-9434000000-b55c6091b4d8a27d70d22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 40V, Positive-QTOFsplash10-0a4l-9000000000-71382d945a6f624527282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 10V, Negative-QTOFsplash10-056r-7009000000-2d03ff18c9997b38b2d82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 20V, Negative-QTOFsplash10-0a4i-9000000000-989d9940c0b7c715d5b32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 40V, Negative-QTOFsplash10-0006-9000000000-1dbaabbf4e0297e1818a2021-09-22Wishart 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 Compound5282918
PDB IDNot Available
ChEBI ID52347
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.