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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 08:39:17 UTC
Update Date2021-09-16 15:27:28 UTC
HMDB IDHMDB0003990
Secondary Accession Numbers
  • HMDB03990
Metabolite Identification
Common Name3b,5a,6b-Cholestanetriol
DescriptionPE(16:0/18:0) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. PE(16:0/18:0), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one octadecanoyl to the C-2 atom. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.
Structure
Data?1582752294
Synonyms
ValueSource
1-Hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamineChEBI
1-Palmitoyl-2-stearoyl-sn-glycero-3-phosphoethanolamine zwitterionChEBI
2-Ammonioethyl (2R)-3-(palmitoyloxy)-2-(stearoyloxy)propyl phosphateChEBI
2-Ammonioethyl (2R)-3-(palmitoyloxy)-2-(stearoyloxy)propyl phosphoric acidGenerator
1-Palmitoyl-2-stearoyl-sn-glycero-3-phosphoethanolamineHMDB
PE(34:0)HMDB
Phophatidylethanolamine(16:0/18:0)HMDB
GPEtn(34:0)HMDB
Phophatidylethanolamine(34:0)HMDB
GPEtn(16:0/18:0)HMDB
3beta,5alpha,6beta-CholestanetriolChEBI
3beta,5alpha,6beta-TrihydroxycholestaneChEBI
Cholestane-3-beta,5-alpha,6-beta-triolChEBI
Cholestane-3beta-5alpha,6beta-triolChEBI
3β,5α,6β-cholestanetriolGenerator
3b,5a,6b-TrihydroxycholestaneGenerator
3β,5α,6β-trihydroxycholestaneGenerator
Cholestane-3-b,5-a,6-b-triolGenerator
Cholestane-3-β,5-α,6-β-triolGenerator
Cholestane-3b-5a,6b-triolGenerator
Cholestane-3β-5α,6β-triolGenerator
5-alpha,6-beta-DihydroxycholestanolHMDB
5alpha,6beta-DihydroxycholestanolHMDB
Cholesta-3beta,5alpha,6beta-triolHMDB
Cholestane-3,5,6-triolHMDB, MeSH
Cholestane-3beta,5alpha,6beta-triolHMDB
CTHMDB
Cholestane-3,5,6-triol, (3beta, 5beta, 6beta)-isomerMeSH, HMDB
Cholestane-3,5,6-triol, (3beta, 6beta)-isomerMeSH, HMDB
Cholestane-3 beta,5 alpha,6 beta-triolMeSH, HMDB
5alpha-Cholestane-3beta,5,6beta-triolMeSH, HMDB
Cholestane-3,5,6-triol, (3beta, 5alpha, 6alpha)-isomerMeSH, HMDB
Cholestane-3,5,6-triol, (3beta)-isomerMeSH, HMDB
Cholestane-3,5,6-triol, (3beta, 5alpha, 6beta)-isomerMeSH, HMDB
3b,5a,6b-CholestanetriolGenerator
5a,6b-DihydroxycholestanolGenerator, HMDB
5Α,6β-dihydroxycholestanolGenerator, HMDB
Chemical FormulaC27H48O3
Average Molecular Weight420.6682
Monoisotopic Molecular Weight420.360345402
IUPAC Name(1S,2R,5S,7R,8R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,7,8-triol
Traditional Namecholestane-3β,5α,6β-triol
CAS Registry Number1253-84-5
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)[C@@]2(O)C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C27H48O3/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24(29)27(30)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28-30H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27+/m1/s1
InChI KeyYMMFNKXZULYSOQ-RUXQDQFYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct ParentPhosphatidylethanolamines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Primary amine
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

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 Solubility0.0018 g/LALOGPS
logP10(5.11) g/LALOGPS
logP10(5.21) g/LChemAxon
logS10(-5.4) g/LALOGPS
pKa (Strongest Acidic)13.29ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.61 m³·mol⁻¹ChemAxon
Polarizability52.7 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
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]+204.17631661259
DarkChem[M-H]-200.73531661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3b,5a,6b-Cholestanetriol[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)[C@@]2(O)C[C@@H](O)CC[C@]12C2881.5Standard polar33892256
3b,5a,6b-Cholestanetriol[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)[C@@]2(O)C[C@@H](O)CC[C@]12C3387.0Standard non polar33892256
3b,5a,6b-Cholestanetriol[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)[C@@]2(O)C[C@@H](O)CC[C@]12C3588.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3b,5a,6b-Cholestanetriol,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C)[C@@]4(O)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3352.5Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,1TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O[Si](C)(C)C)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3308.0Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,1TMS,isomer #3CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O)C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3347.1Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C)[C@@]4(O[Si](C)(C)C)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3269.8Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C)[C@@]4(O)C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3286.0Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TMS,isomer #3CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3247.2Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,3TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C)[C@@]4(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3257.3Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]4(O)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3595.6Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,1TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O[Si](C)(C)C(C)(C)C)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3537.2Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,1TBDMS,isomer #3CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O)C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3608.8Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]4(O[Si](C)(C)C(C)(C)C)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3715.0Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]4(O)C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3774.5Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TBDMS,isomer #3CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3718.8Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,3TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]4(O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3921.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3b,5a,6b-Cholestanetriol GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vi-1219200000-8d218b1547f718fefb612017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,5a,6b-Cholestanetriol GC-MS (3 TMS) - 70eV, Positivesplash10-00di-3111059000-2015192f14f9faab4bbe2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,5a,6b-Cholestanetriol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,5a,6b-Cholestanetriol 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 - 3b,5a,6b-Cholestanetriol 10V, Positive-QTOFsplash10-0uk9-0003900000-853df66410948bb19a9e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 20V, Positive-QTOFsplash10-0fe0-4129600000-d4fc2d8df176fb497ed52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 40V, Positive-QTOFsplash10-0abi-8249000000-86d9b22e1f9506f0ed1c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 10V, Negative-QTOFsplash10-014i-0000900000-22df76beb29491934a982017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 20V, Negative-QTOFsplash10-0gb9-0001900000-0f11b3056c8453dc75922017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 40V, Negative-QTOFsplash10-0zg1-2009300000-319c3b30d049804da1b12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 10V, Positive-QTOFsplash10-00di-0000900000-43d1925358840679cd312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 20V, Positive-QTOFsplash10-05fr-9332200000-e5493620a11f0ba7b2f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 40V, Positive-QTOFsplash10-0abd-9651000000-48cc8cf6870e160176742021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 10V, Negative-QTOFsplash10-014i-0000900000-722417cd9cab9945ab4a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 20V, Negative-QTOFsplash10-014i-0000900000-f6043fb123be98cf63742021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,5a,6b-Cholestanetriol 40V, Negative-QTOFsplash10-014i-0004900000-d603230f2d7d3e87bf402021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothInflammatory bowel disease details
Associated Disorders and Diseases
Disease References
Inflammatory bowel disease
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB026115
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5326793
PDB IDNot Available
ChEBI ID73006
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceFieser, Louis F.; Rajagopalan, Srinivasa. Selective oxidation with N-bromosuccinimide. II. Cholestane-3b,5a,6b-triol. Journal of the American Chemical Society (1949), 71 3938-41.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bjorkhem I, Breuer O, Angelin B, Wikstrom SA: Assay of unesterified cholesterol-5,6-epoxide in human serum by isotope dilution mass spectrometry. Levels in the healthy state and in hyperlipoproteinemia. J Lipid Res. 1988 Aug;29(8):1031-8. [PubMed:3183516 ]