Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-10-15 12:12:16 UTC
Update Date2022-03-07 02:51:03 UTC
HMDB IDHMDB0010737
Secondary Accession Numbers
  • HMDB10737
Metabolite Identification
Common Name(R)-3-Hydroxy-Octadecanoic acid
Description(R)-3-Hydroxy-Octadecanoic acid, also known as 3R-hydroxy-octadecanoate, 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 (R)-3-Hydroxy-Octadecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752867
Synonyms
ValueSource
(R)-3-Hydroxy-octadecanoateGenerator
3R-Hydroxy-octadecanoateHMDB
Chemical FormulaC18H36O3
Average Molecular Weight300.4766
Monoisotopic Molecular Weight300.266445018
IUPAC Name(3R)-3-hydroxyoctadecanoic acid
Traditional Name(3R)-3-hydroxyoctadecanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(CCCCCCCCCCCCCCC)CC(O)=O
InChI Identifier
InChI=1S/C18H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17(19)16-18(20)21/h17,19H,2-16H2,1H3,(H,20,21)/t17-/m1/s1
InChI KeyPOMQYTSPMKEQNB-QGZVFWFLSA-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
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 Solubility0.0015 g/LALOGPS
logP6.83ALOGPS
logP5.91ChemAxon
logS-5.3ALOGPS
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 Count16ChemAxon
Refractivity87.8 m³·mol⁻¹ChemAxon
Polarizability39.38 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]+180.32231661259
DarkChem[M-H]-177.52331661259
DeepCCS[M+H]+173.33630932474
DeepCCS[M-H]-170.97830932474
DeepCCS[M-2H]-204.18330932474
DeepCCS[M+Na]+179.42930932474
AllCCS[M+H]+186.032859911
AllCCS[M+H-H2O]+183.132859911
AllCCS[M+NH4]+188.632859911
AllCCS[M+Na]+189.432859911
AllCCS[M-H]-181.032859911
AllCCS[M+Na-2H]-182.232859911
AllCCS[M+HCOO]-183.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-3-Hydroxy-Octadecanoic acid[H][C@@](O)(CCCCCCCCCCCCCCC)CC(O)=O3435.5Standard polar33892256
(R)-3-Hydroxy-Octadecanoic acid[H][C@@](O)(CCCCCCCCCCCCCCC)CC(O)=O2220.1Standard non polar33892256
(R)-3-Hydroxy-Octadecanoic acid[H][C@@](O)(CCCCCCCCCCCCCCC)CC(O)=O2380.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-3-Hydroxy-Octadecanoic acid,1TMS,isomer #1CCCCCCCCCCCCCCC[C@H](CC(=O)O)O[Si](C)(C)C2378.9Semi standard non polar33892256
(R)-3-Hydroxy-Octadecanoic acid,1TMS,isomer #2CCCCCCCCCCCCCCC[C@@H](O)CC(=O)O[Si](C)(C)C2354.6Semi standard non polar33892256
(R)-3-Hydroxy-Octadecanoic acid,2TMS,isomer #1CCCCCCCCCCCCCCC[C@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2442.3Semi standard non polar33892256
(R)-3-Hydroxy-Octadecanoic acid,1TBDMS,isomer #1CCCCCCCCCCCCCCC[C@H](CC(=O)O)O[Si](C)(C)C(C)(C)C2630.5Semi standard non polar33892256
(R)-3-Hydroxy-Octadecanoic acid,1TBDMS,isomer #2CCCCCCCCCCCCCCC[C@@H](O)CC(=O)O[Si](C)(C)C(C)(C)C2614.5Semi standard non polar33892256
(R)-3-Hydroxy-Octadecanoic acid,2TBDMS,isomer #1CCCCCCCCCCCCCCC[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2925.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxy-Octadecanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9580000000-5c278ff8dd48f96e4dc72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxy-Octadecanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00b9-9313100000-c255193ae69203b857a22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxy-Octadecanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-3-Hydroxy-Octadecanoic 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 - (R)-3-Hydroxy-Octadecanoic acid 10V, Positive-QTOFsplash10-001i-0091000000-11da7a1c6a2fd3fd8ad22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-Octadecanoic acid 20V, Positive-QTOFsplash10-00m0-2290000000-5e613b8ee1cddd5b7de22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-Octadecanoic acid 40V, Positive-QTOFsplash10-052g-8930000000-67a1788a6422ceaaa5842017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-Octadecanoic acid 10V, Negative-QTOFsplash10-0002-0090000000-c1f443881c9074c73e742017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-Octadecanoic acid 20V, Negative-QTOFsplash10-0a5i-2090000000-57fc0fb89c504d4bd99f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-Octadecanoic acid 40V, Negative-QTOFsplash10-0a4u-9060000000-e50655f588f888c3ff222017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-Octadecanoic acid 10V, Negative-QTOFsplash10-0002-1090000000-e27ec23f0c5d239db8422021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-Octadecanoic acid 20V, Negative-QTOFsplash10-0a4i-9020000000-216bf02e4a44af3051992021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-Octadecanoic acid 40V, Negative-QTOFsplash10-052f-9020000000-70b91800640608f5b2c42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-Octadecanoic acid 10V, Positive-QTOFsplash10-0ue9-2196000000-a2b72594e167052997872021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-Octadecanoic acid 20V, Positive-QTOFsplash10-0l1l-9461000000-2f611a529518f12ff8722021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-3-Hydroxy-Octadecanoic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-bd05dc1717e2d25c080e2021-09-25Wishart 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 IDFDB027884
KNApSAcK IDNot Available
Chemspider ID4472263
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5312838
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.

Enzymes

General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
P49327
Molecular weight:
273424.06