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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 21:09:59 UTC
Update Date2021-09-14 15:19:06 UTC
HMDB IDHMDB0006281
Secondary Accession Numbers
  • HMDB06281
Metabolite Identification
Common Name7-a,27-Dihydroxycholesterol
Description7-a,27-Dihydroxycholesterol, also known as cholest-5-ene-3b,7a,26-triol, belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. Thus, 7-a,27-dihydroxycholesterol is considered to be a bile acid lipid molecule. 7-a,27-Dihydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752379
Synonyms
ValueSource
5-Cholestene-3beta,7alpha,26-triolChEBI
7-alpha,27-DihydroxycholesterolChEBI
Cholest-5-ene-3beta,7alpha,26-triolChEBI
Cholest-5-ene-3beta,7alpha,27-triolChEBI
5-Cholestene-3b,7a,26-triolGenerator
5-Cholestene-3β,7α,26-triolGenerator
7-Α,27-dihydroxycholesterolGenerator
Cholest-5-ene-3b,7a,26-triolGenerator
Cholest-5-ene-3β,7α,26-triolGenerator
Cholest-5-ene-3b,7a,27-triolGenerator
Cholest-5-ene-3β,7α,27-triolGenerator
7alpha,26-DihydroxycholesterolHMDB
7alpha,27-DihydroxycholesterolHMDB
Cholest-5-ene-3,7,27-triolHMDB
Cholest-5-ene-3- b,7-a,27-triolHMDB
Cholest-5-ene-3-b,7-a,27-triolHMDB
Cholest-5-ene-3-beta,7-alpha,27-triolHMDB
Chemical FormulaC27H46O3
Average Molecular Weight418.6523
Monoisotopic Molecular Weight418.344695338
IUPAC Name(1S,2R,5S,9S,10S,11S,14R,15R)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
Traditional Name7α,27-dihydroxycholesterol
CAS Registry Number4725-24-0
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)CO
InChI Identifier
InChI=1S/C27H46O3/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/h15,17-18,20-25,28-30H,5-14,16H2,1-4H3/t17?,18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1
InChI KeyRXMHNAKZMGJANZ-DTTSCKGMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • 26-hydroxysteroid
  • Trihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Fatty alcohol
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Primary alcohol
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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 Solubility0.0051 g/LALOGPS
logP10(4.67) g/LALOGPS
logP10(4.6) g/LChemAxon
logS10(-4.9) g/LALOGPS
pKa (Strongest Acidic)17.42ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.91 m³·mol⁻¹ChemAxon
Polarizability52.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+204.27631661259
DarkChem[M-H]-197.70131661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7-a,27-Dihydroxycholesterol,1TMS,#1CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3496.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
7-a,27-Dihydroxycholesterol,1TMS,#2CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3501.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
7-a,27-Dihydroxycholesterol,1TMS,#3CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C3505.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
7-a,27-Dihydroxycholesterol,2TMS,#1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C3467.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
7-a,27-Dihydroxycholesterol,2TMS,#2CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3415.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
7-a,27-Dihydroxycholesterol,2TMS,#3CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C3502.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
7-a,27-Dihydroxycholesterol,3TMS,#1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C3399.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
7-a,27-Dihydroxycholesterol,1TBDMS,#1CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3730.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
7-a,27-Dihydroxycholesterol,1TBDMS,#2CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3723.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
7-a,27-Dihydroxycholesterol,1TBDMS,#3CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C(C)(C)C3765.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
7-a,27-Dihydroxycholesterol,2TBDMS,#1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C(C)(C)C3957.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
7-a,27-Dihydroxycholesterol,2TBDMS,#2CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3878.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
7-a,27-Dihydroxycholesterol,2TBDMS,#3CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C(C)(C)C3983.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
7-a,27-Dihydroxycholesterol,3TBDMS,#1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C(C)(C)C4106.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7-a,27-Dihydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0139300000-221e3200779e0697d0172017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-a,27-Dihydroxycholesterol GC-MS (3 TMS) - 70eV, Positivesplash10-00xr-1310149000-0a3195294de24630bcb52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-a,27-Dihydroxycholesterol 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-a,27-Dihydroxycholesterol 10V, Positive-QTOFsplash10-0ue9-0006900000-c1354f70aeba87e8bddf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,27-Dihydroxycholesterol 20V, Positive-QTOFsplash10-0f89-1009300000-a1e89f6c04fc2d2865d12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,27-Dihydroxycholesterol 40V, Positive-QTOFsplash10-062c-3029000000-d0d93103295de6ed3d2c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,27-Dihydroxycholesterol 10V, Negative-QTOFsplash10-014i-0006900000-6b334d55dd76faff4df82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,27-Dihydroxycholesterol 20V, Negative-QTOFsplash10-014j-0009400000-c2983b5dbb3cbfbf357e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,27-Dihydroxycholesterol 40V, Negative-QTOFsplash10-00dr-2009100000-2e80feb58d681f70a6f92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,27-Dihydroxycholesterol 10V, Negative-QTOFsplash10-014i-0002900000-a0815d1227c30636020c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,27-Dihydroxycholesterol 20V, Negative-QTOFsplash10-014i-0003900000-810b115febb00f469d252021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,27-Dihydroxycholesterol 40V, Negative-QTOFsplash10-014i-0003900000-558c2f025f3c29e2e9522021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,27-Dihydroxycholesterol 10V, Positive-QTOFsplash10-0uxr-1202900000-bd6f4c8c658841ee2d202021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,27-Dihydroxycholesterol 20V, Positive-QTOFsplash10-001i-6359400000-afbc03ffc36e1b4230242021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-a,27-Dihydroxycholesterol 40V, Positive-QTOFsplash10-0abi-7950000000-0145ada702a586b3b6642021-09-25Wishart 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 IDFDB023875
KNApSAcK IDNot Available
Chemspider ID389810
KEGG Compound IDC06341
BioCyc IDNot Available
BiGG ID48023
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440985
PDB IDNot Available
ChEBI ID18431
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 ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes a rate-limiting step in cholesterol catabolism and bile acid biosynthesis by introducing a hydrophilic moiety at position 7 of cholesterol. Important for cholesterol homeostasis.
Gene Name:
CYP7A1
Uniprot ID:
P22680
Molecular weight:
57660.155
Reactions
27-Hydroxycholesterol + NADPH + Hydrogen Ion + Oxygen → 7-a,27-Dihydroxycholesterol + NADP + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP7B1
Uniprot ID:
O75881
Molecular weight:
58255.325
Reactions
27-Hydroxycholesterol + NADPH + Oxygen → 7-a,27-Dihydroxycholesterol + NADP + Waterdetails
27-Hydroxycholesterol + NADPH + Hydrogen Ion + Oxygen → 7-a,27-Dihydroxycholesterol + 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