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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-13 14:03:09 UTC
Update Date2021-09-16 15:29:10 UTC
HMDB IDHMDB0012459
Secondary Accession Numbers
  • HMDB12459
Metabolite Identification
Common Name7 alpha,26-Dihydroxy-4-cholesten-3-one
Description7 alpha,26-Dihydroxy-4-cholesten-3-one, also known as 4-cholesten-7alpha,26-diol-3-one or 7,26-dhxyclso, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. 7 alpha,26-Dihydroxy-4-cholesten-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582753057
Synonyms
ValueSource
7 a,26-Dihydroxy-4-cholesten-3-oneGenerator
7 Α,26-dihydroxy-4-cholesten-3-oneGenerator
(7alpha)-7,26-Dihydroxy-cholest-4-en-3-oneHMDB
4-Cholesten-7alpha,26-diol-3-oneHMDB
7,26-DhxyclsoHMDB
7alpha,26-Dihydroxy-4-cholesten-3-oneHMDB
7alpha,26-Dihydroxycholest-4-en-3-oneHMDB
Chemical FormulaC27H44O3
Average Molecular Weight416.6365
Monoisotopic Molecular Weight416.329045274
IUPAC Name(2R,9R,15R)-9-hydroxy-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name(2R,9R,15R)-9-hydroxy-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
CAS Registry Number4675-38-1
SMILES
CC(CO)CCC[C@@H](C)C1CCC2C3[C@H](O)CC4=CC(=O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier
InChI=1S/C27H44O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-25-23(11-13-27(21,22)4)26(3)12-10-20(29)14-19(26)15-24(25)30/h14,17-18,21-25,28,30H,5-13,15-16H2,1-4H3/t17?,18-,21?,22?,23?,24-,25?,26+,27-/m1/s1
InChI KeyKVJVJJWIEXCECB-JZGXDVPNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • 26-hydroxysteroid
  • Dihydroxy bile acid, alcohol, or derivatives
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 7-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Fatty alcohol
  • Cyclohexenone
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Cyclic ketone
  • Ketone
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0029 g/LALOGPS
logP10(4.6) g/LALOGPS
logP10(5.01) g/LChemAxon
logS10(-5.2) g/LALOGPS
pKa (Strongest Acidic)17.14ChemAxon
pKa (Strongest Basic)-0.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.01 m³·mol⁻¹ChemAxon
Polarizability50.79 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+199.18531661259
DarkChem[M-H]-193.33831661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7 alpha,26-Dihydroxy-4-cholesten-3-one,1TMS,#1CC(CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O)CO[Si](C)(C)C3646.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
7 alpha,26-Dihydroxy-4-cholesten-3-one,1TMS,#2CC(CO)CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C3642.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
7 alpha,26-Dihydroxy-4-cholesten-3-one,1TMS,#3CC(CO)CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O3540.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
7 alpha,26-Dihydroxy-4-cholesten-3-one,2TMS,#1CC(CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C)CO[Si](C)(C)C3647.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
7 alpha,26-Dihydroxy-4-cholesten-3-one,2TMS,#2CC(CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O)CO[Si](C)(C)C3549.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
7 alpha,26-Dihydroxy-4-cholesten-3-one,2TMS,#3CC(CO)CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O[Si](C)(C)C3507.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
7 alpha,26-Dihydroxy-4-cholesten-3-one,1TBDMS,#1CC(CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O)CO[Si](C)(C)C(C)(C)C3889.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
7 alpha,26-Dihydroxy-4-cholesten-3-one,1TBDMS,#2CC(CO)CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C3851.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
7 alpha,26-Dihydroxy-4-cholesten-3-one,1TBDMS,#3CC(CO)CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O3767.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
7 alpha,26-Dihydroxy-4-cholesten-3-one,2TBDMS,#1CC(CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C4089.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
7 alpha,26-Dihydroxy-4-cholesten-3-one,2TBDMS,#2CC(CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O)CO[Si](C)(C)C(C)(C)C4014.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
7 alpha,26-Dihydroxy-4-cholesten-3-one,2TBDMS,#3CC(CO)CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C3925.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7 alpha,26-Dihydroxy-4-cholesten-3-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-0359200000-c5e766bc8da3445acdea2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7 alpha,26-Dihydroxy-4-cholesten-3-one GC-MS (2 TMS) - 70eV, Positivesplash10-0002-1220390000-2ea93ad32d390af352da2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7 alpha,26-Dihydroxy-4-cholesten-3-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7 alpha,26-Dihydroxy-4-cholesten-3-one 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 - 7 alpha,26-Dihydroxy-4-cholesten-3-one 10V, Positive-QTOFsplash10-00kb-0009200000-f13064ffc70da2c2b57d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7 alpha,26-Dihydroxy-4-cholesten-3-one 20V, Positive-QTOFsplash10-00l2-1009000000-f344cdc48d7b49f22d6f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7 alpha,26-Dihydroxy-4-cholesten-3-one 40V, Positive-QTOFsplash10-016r-3129000000-b6c48651e7e9ac09edbc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7 alpha,26-Dihydroxy-4-cholesten-3-one 10V, Negative-QTOFsplash10-014i-0004900000-7754503899cd9db211c42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7 alpha,26-Dihydroxy-4-cholesten-3-one 20V, Negative-QTOFsplash10-014j-0009600000-54c6b067e6490ab83b852017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7 alpha,26-Dihydroxy-4-cholesten-3-one 40V, Negative-QTOFsplash10-0674-2009000000-ceacf291ac96437f59442017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7 alpha,26-Dihydroxy-4-cholesten-3-one 10V, Positive-QTOFsplash10-014j-0006900000-1bab66a6ddf2f8b577e82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7 alpha,26-Dihydroxy-4-cholesten-3-one 20V, Positive-QTOFsplash10-07wj-5749100000-fb55e94ae37f95aa32a82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7 alpha,26-Dihydroxy-4-cholesten-3-one 40V, Positive-QTOFsplash10-0a4i-9850000000-4478cbe8a6ea3e417fe22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7 alpha,26-Dihydroxy-4-cholesten-3-one 10V, Negative-QTOFsplash10-014i-0000900000-67ea14fb7a26b9b2d9292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7 alpha,26-Dihydroxy-4-cholesten-3-one 20V, Negative-QTOFsplash10-014i-0005900000-37c9645751a2f52b74242021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7 alpha,26-Dihydroxy-4-cholesten-3-one 40V, Negative-QTOFsplash10-03di-0004900000-ca04c33318a7e2c042bc2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
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 IDFDB029075
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC17336
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481412
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 monooxygenase activity
Specific function:
Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:
CYP27A1
Uniprot ID:
Q02318
Molecular weight:
60234.28
Reactions
7 alpha,26-Dihydroxy-4-cholesten-3-one + Oxygen + NADPH + Hydrogen Ion → 7alpha-Hydroxy-3-oxo-4-cholestenoate + NADP + Waterdetails
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
7-a,27-Dihydroxycholesterol + NAD → 7 alpha,26-Dihydroxy-4-cholesten-3-one + NADH + Hydrogen Iondetails