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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:26:15 UTC
Update Date2022-03-07 03:17:46 UTC
HMDB IDHMDB0060512
Secondary Accession Numbers
  • HMDB60512
Metabolite Identification
Common NameSterol
DescriptionSterols, also known as steroid alcohols, are a subgroup of the steroids and an important class of organic molecules. They occur naturally in plants, animals, and fungi, with the most familiar type of animal sterol being cholesterol. Cholesterol is vital to animal cell membrane structure and function and a precursor to fat-soluble vitamins and steroid hormones. (Wikipedia )
Structure
Data?1563866070
Synonyms
ValueSource
SterolsMeSH
Chemical FormulaC17H28O
Average Molecular Weight248.4036
Monoisotopic Molecular Weight248.214015518
IUPAC Nametetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol
Traditional Namesterol
CAS Registry NumberNot Available
SMILES
OC1CCC2C(CCC3C4CCCC4CCC23)C1
InChI Identifier
InChI=1S/C17H28O/c18-13-6-9-15-12(10-13)5-8-16-14-3-1-2-11(14)4-7-17(15)16/h11-18H,1-10H2
InChI KeyFPXSXMFOYWRHDX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-hydroxysteroids. These are steroids carrying a hydroxyl group at the 3-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent3-hydroxysteroids
Alternative Parents
Substituents
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

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 Solubility0.00059 g/LALOGPS
logP4.57ALOGPS
logP3.83ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)18.31ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity74.17 m³·mol⁻¹ChemAxon
Polarizability31.24 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+160.9231661259
DarkChem[M-H]-156.55731661259
DeepCCS[M-2H]-199.22430932474
DeepCCS[M+Na]+174.73430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SterolOC1CCC2C(CCC3C4CCCC4CCC23)C12626.0Standard polar33892256
SterolOC1CCC2C(CCC3C4CCCC4CCC23)C12151.7Standard non polar33892256
SterolOC1CCC2C(CCC3C4CCCC4CCC23)C12208.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sterol,1TMS,isomer #1C[Si](C)(C)OC1CCC2C(CCC3C4CCCC4CCC23)C12254.1Semi standard non polar33892256
Sterol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCC2C(CCC3C4CCCC4CCC23)C12505.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gi9-1690000000-34b26e814ee44384b8db2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sterol GC-MS (1 TMS) - 70eV, Positivesplash10-0006-4592000000-9a85a23a5cffd078c0cc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sterol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterol 10V, Positive-QTOFsplash10-001j-0190000000-10353145ba0de714b5f62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterol 20V, Positive-QTOFsplash10-001j-3690000000-3794e683abf7010e49982016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterol 40V, Positive-QTOFsplash10-0uy3-6950000000-3e0f62c61d1db26039a72016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterol 10V, Negative-QTOFsplash10-0002-0090000000-53e5c105aaf3633b48842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterol 20V, Negative-QTOFsplash10-0002-0090000000-c988565144a133794da32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterol 40V, Negative-QTOFsplash10-0159-2290000000-98a92e5f36881f1607ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterol 10V, Positive-QTOFsplash10-000t-0090000000-1c2f310039cdedd9adc32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterol 20V, Positive-QTOFsplash10-0002-0190000000-098342cc11a5134feb142021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterol 40V, Positive-QTOFsplash10-01wb-3910000000-a7b52e7834ee5513f59c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterol 10V, Negative-QTOFsplash10-0002-0090000000-1cd5462e3d6d0188b8952021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterol 20V, Negative-QTOFsplash10-002b-0090000000-d6b481aaa0a2353a02f52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterol 40V, Negative-QTOFsplash10-0002-0090000000-ddea965f6d6927c3177d2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDFDB003714
KNApSAcK IDC00002159
Chemspider ID1076
KEGG Compound IDC00370
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSterol
METLIN IDNot Available
PubChem Compound1107
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. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:
Central enzyme in the extracellular metabolism of plasma lipoproteins. Synthesized mainly in the liver and secreted into plasma where it converts cholesterol and phosphatidylcholines (lecithins) to cholesteryl esters and lysophosphatidylcholines on the surface of high and low density lipoproteins (HDLs and LDLs). The cholesterol ester is then transported back to the liver. Has a preference for plasma 16:0-18:2 or 18:O-18:2 phosphatidylcholines. Also produced in the brain by primary astrocytes, and esterifies free cholesterol on nascent APOE-containing lipoproteins secreted from glia and influences cerebral spinal fluid (CSF) APOE- and APOA1 levels. Together with APOE and the cholesterol transporter ABCA1, plays a key role in the maturation of glial-derived, nascent lipoproteins. Required for remodeling high-density lipoprotein particles into their spherical forms.
Gene Name:
LCAT
Uniprot ID:
P04180
Molecular weight:
49577.545
Reactions
Phosphatidylcholine + Sterol → 1-Acyl-sn-glycero-3-phosphocholine + Steryl esterdetails