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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2021-09-14 15:40:08 UTC
HMDB IDHMDB0059592
Secondary Accession Numbers
  • HMDB59592
Metabolite Identification
Common NameCholest-5-ene-3-beta,7-alpha-diol
DescriptionCholest-5-ene-3-beta,7-alpha-diol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Cholest-5-ene-3-beta,7-alpha-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563865952
Synonyms
ValueSource
Cholest-5-ene-3-b,7-a-diolGenerator
Cholest-5-ene-3-β,7-α-diolGenerator
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
Traditional Name(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(O)C=C2CC(O)CC[C@]12C
InChI Identifier
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20?,21-,22+,23+,24?,25+,26+,27-/m1/s1
InChI KeyOYXZMSRRJOYLLO-LOKCBIGLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • Cholesterol
  • 7-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

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 Solubility0.00048 g/LALOGPS
logP10(5.61) g/LALOGPS
logP10(5.96) g/LChemAxon
logS10(-5.9) g/LALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.06 m³·mol⁻¹ChemAxon
Polarizability51.33 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]+199.15331661259
DarkChem[M-H]-194.6531661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cholest-5-ene-3-beta,7-alpha-diol[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(O)C=C2CC(O)CC[C@]12C2482.2Standard polar33892256
Cholest-5-ene-3-beta,7-alpha-diol[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(O)C=C2CC(O)CC[C@]12C3274.9Standard non polar33892256
Cholest-5-ene-3-beta,7-alpha-diol[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(O)C=C2CC(O)CC[C@]12C3325.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cholest-5-ene-3-beta,7-alpha-diol,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)C=C4CC(O)CC[C@]4(C)[C@H]3CC[C@@]21C3291.0Semi standard non polar33892256
Cholest-5-ene-3-beta,7-alpha-diol,1TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O)C=C4CC(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3296.1Semi standard non polar33892256
Cholest-5-ene-3-beta,7-alpha-diol,2TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)C=C4CC(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3243.1Semi standard non polar33892256
Cholest-5-ene-3-beta,7-alpha-diol,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)C=C4CC(O)CC[C@]4(C)[C@H]3CC[C@@]21C3528.2Semi standard non polar33892256
Cholest-5-ene-3-beta,7-alpha-diol,1TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O)C=C4CC(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3538.4Semi standard non polar33892256
Cholest-5-ene-3-beta,7-alpha-diol,2TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)C=C4CC(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3738.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cholest-5-ene-3-beta,7-alpha-diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-1229000000-bbd29b0148240a6e8a342017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cholest-5-ene-3-beta,7-alpha-diol GC-MS (2 TMS) - 70eV, Positivesplash10-001i-6110590000-b66f740fbc107b812df82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cholest-5-ene-3-beta,7-alpha-diol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cholest-5-ene-3-beta,7-alpha-diol 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 - Cholest-5-ene-3-beta,7-alpha-diol 10V, Positive-QTOFsplash10-0f79-0009200000-a31b2c397468b45366b22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene-3-beta,7-alpha-diol 20V, Positive-QTOFsplash10-00kr-2129100000-4fac15b3ff2261008e912017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene-3-beta,7-alpha-diol 40V, Positive-QTOFsplash10-0a4i-5249000000-b8ddfa6034e8a89a74ae2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene-3-beta,7-alpha-diol 10V, Negative-QTOFsplash10-0udi-0003900000-554f04a87ac749f5ccde2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene-3-beta,7-alpha-diol 20V, Negative-QTOFsplash10-0ue9-0008900000-b67edccfb405ce918eb12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene-3-beta,7-alpha-diol 40V, Negative-QTOFsplash10-01bi-1009000000-111324aaf6701d08d72a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene-3-beta,7-alpha-diol 10V, Positive-QTOFsplash10-0udi-0004900000-9288fad411a38b9398d52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene-3-beta,7-alpha-diol 20V, Positive-QTOFsplash10-0avi-9337200000-e66f19d5695257f4d2ce2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene-3-beta,7-alpha-diol 40V, Positive-QTOFsplash10-0adi-7931000000-a2cf8613e72e1e1294572021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene-3-beta,7-alpha-diol 10V, Negative-QTOFsplash10-0udi-0000900000-079f76b4d985e4b92c9d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene-3-beta,7-alpha-diol 20V, Negative-QTOFsplash10-0udi-0000900000-079f76b4d985e4b92c9d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholest-5-ene-3-beta,7-alpha-diol 40V, Negative-QTOFsplash10-0udj-0019600000-41ecc9c69637f280d0402021-09-22Wishart 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 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 Compound22826216
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. Dietschy JM, Turley SD: Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J Lipid Res. 2004 Aug;45(8):1375-97. [PubMed:15254070 ]
  6. O'Byrne SM, Blaner WS: Retinol and retinyl esters: biochemistry and physiology. J Lipid Res. 2013 Jul;54(7):1731-43. doi: 10.1194/jlr.R037648. Epub 2013 Apr 26. [PubMed:23625372 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  8. Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..

Enzymes

General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. HSD VII is active against four 7-alpha-hydroxylated sterols. Does not metabolize several different C(19/21) steroids as substrates. Involved in bile acid synthesis.
Gene Name:
HSD3B7
Uniprot ID:
Q9H2F3
Molecular weight:
21322.265
Reactions
Cholest-5-ene-3-beta,7-alpha-diol + NAD → 7a-Hydroxy-cholestene-3-one + NADHdetails