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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-06 15:50:48 UTC
Update Date2021-09-14 15:40:18 UTC
HMDB IDHMDB0006763
Secondary Accession Numbers
  • HMDB06763
Metabolite Identification
Common Name20a,22b-Dihydroxycholesterol
Description20alpha,22beta-Dihydroxycholesterol is an intermediate in C21-Steroid hormone metabolism. 20alpha,22beta-Dihydroxycholesterol is the 8th to last step in the synthesis of 3alpha,11beta,21-Trihydroxy-20-oxo-5beta-pregnan-18-al and is converted from 20alpha-Hydroxycholesterol via the enzyme cytochrome P450 (EC 1.14.15.6). It is then converted to Pregnenolone via the enzyme cytochrome P450 (EC 1.14.15.6).
Structure
Data?1582752404
Synonyms
ValueSource
20alpha,22beta-DihydroxycholesterolHMDB
Chemical FormulaC27H46O3
Average Molecular Weight418.6523
Monoisotopic Molecular Weight418.344695338
IUPAC Name(2R,3R)-2-[(1S,2R,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-6-methylheptane-2,3-diol
Traditional Name(2R,3R)-2-[(1S,2R,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-6-methylheptane-2,3-diol
CAS Registry Number15234-55-6
SMILES
[H][C@@]12CC[C@]([H])([C@@](C)(O)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(O)CC[C@]12C
InChI Identifier
InChI=1S/C27H46O3/c1-17(2)6-11-24(29)27(5,30)23-10-9-21-20-8-7-18-16-19(28)12-14-25(18,3)22(20)13-15-26(21,23)4/h7,17,19-24,28-30H,6,8-16H2,1-5H3/t19?,20-,21-,22-,23-,24+,25-,26-,27+/m0/s1
InChI KeyISBSSBGEYIBVTO-IVMOZYHGSA-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
  • Cholesterol
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • Trihydroxy bile acid, alcohol, or derivatives
  • 22-hydroxysteroid
  • 20-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Secondary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • 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 Solubility0.008 g/LALOGPS
logP10(5.08) g/LALOGPS
logP10(4.72) g/LChemAxon
logS10(-4.7) g/LALOGPS
pKa (Strongest Acidic)13.61ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity123.66 m³·mol⁻¹ChemAxon
Polarizability51.5 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.92731661259
DarkChem[M-H]-199.45931661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
20a,22b-Dihydroxycholesterol,1TMS,#1CC(C)CC[C@@H](O)[C@](C)(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(O)CC[C@]4(C)[C@H]3CC[C@@]21C3457.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
20a,22b-Dihydroxycholesterol,1TMS,#2CC(C)CC[C@@H](O[Si](C)(C)C)[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(O)CC[C@]4(C)[C@H]3CC[C@@]21C3456.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
20a,22b-Dihydroxycholesterol,1TMS,#3CC(C)CC[C@@H](O)[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3493.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
20a,22b-Dihydroxycholesterol,2TMS,#1CC(C)CC[C@@H](O[Si](C)(C)C)[C@](C)(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(O)CC[C@]4(C)[C@H]3CC[C@@]21C3501.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
20a,22b-Dihydroxycholesterol,2TMS,#2CC(C)CC[C@@H](O)[C@](C)(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3471.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
20a,22b-Dihydroxycholesterol,2TMS,#3CC(C)CC[C@@H](O[Si](C)(C)C)[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3464.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
20a,22b-Dihydroxycholesterol,3TMS,#1CC(C)CC[C@@H](O[Si](C)(C)C)[C@](C)(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3495.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
20a,22b-Dihydroxycholesterol,1TBDMS,#1CC(C)CC[C@@H](O)[C@](C)(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(O)CC[C@]4(C)[C@H]3CC[C@@]21C3703.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
20a,22b-Dihydroxycholesterol,1TBDMS,#2CC(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(O)CC[C@]4(C)[C@H]3CC[C@@]21C3714.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
20a,22b-Dihydroxycholesterol,1TBDMS,#3CC(C)CC[C@@H](O)[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3730.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
20a,22b-Dihydroxycholesterol,2TBDMS,#1CC(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(O)CC[C@]4(C)[C@H]3CC[C@@]21C4007.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
20a,22b-Dihydroxycholesterol,2TBDMS,#2CC(C)CC[C@@H](O)[C@](C)(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3952.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
20a,22b-Dihydroxycholesterol,2TBDMS,#3CC(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3953.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
20a,22b-Dihydroxycholesterol,3TBDMS,#1CC(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4226.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 20a,22b-Dihydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-4259400000-35c8f139c691d00dfc8e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 20a,22b-Dihydroxycholesterol GC-MS (3 TMS) - 70eV, Positivesplash10-00xr-2111139000-a480b3deb74eef32e3832017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 20a,22b-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 - 20a,22b-Dihydroxycholesterol 10V, Positive-QTOFsplash10-0uxr-1014900000-d02629f92bcfa0d4d5bd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20a,22b-Dihydroxycholesterol 20V, Positive-QTOFsplash10-0ab9-8098400000-ec5061b658871254b4712017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20a,22b-Dihydroxycholesterol 40V, Positive-QTOFsplash10-0a4i-9065000000-9198f9a283da1d4a6a062017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20a,22b-Dihydroxycholesterol 10V, Negative-QTOFsplash10-014i-0003900000-7cd68582455580a1aeeb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20a,22b-Dihydroxycholesterol 20V, Negative-QTOFsplash10-01ba-2397500000-8b9915c82bf3ecb526812017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20a,22b-Dihydroxycholesterol 40V, Negative-QTOFsplash10-00xr-7289100000-1e37d62442300af9ead12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20a,22b-Dihydroxycholesterol 10V, Negative-QTOFsplash10-014i-0000900000-f2cb6399034352e924c82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20a,22b-Dihydroxycholesterol 20V, Negative-QTOFsplash10-014i-0023900000-85cd6f9f87eb3b7457262021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20a,22b-Dihydroxycholesterol 40V, Negative-QTOFsplash10-05o1-4139500000-f72eacbae8e6876f643a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20a,22b-Dihydroxycholesterol 10V, Positive-QTOFsplash10-014i-0021900000-e2e06cd0437b866378242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20a,22b-Dihydroxycholesterol 20V, Positive-QTOFsplash10-001i-4596100000-bb184f1626e9252f10ec2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20a,22b-Dihydroxycholesterol 40V, Positive-QTOFsplash10-0a4i-5930000000-979f3659179997a1c7952021-09-24Wishart 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 IDFDB024066
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05501
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477897
PDB IDNot Available
ChEBI ID1294
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 the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
CYP11A1
Uniprot ID:
P05108
Molecular weight:
60101.87
Reactions
20a,22b-Dihydroxycholesterol + Oxygen + Reduced adrenal ferredoxin + Hydrogen Ion → 4-Methylpentanal + Pregnenolone + Water + Oxidized adrenal ferredoxindetails
20alpha-Hydroxycholesterol + Oxygen + Reduced adrenal ferredoxin + Hydrogen Ion → 20a,22b-Dihydroxycholesterol + Water + Oxidized adrenal ferredoxindetails
22b-Hydroxycholesterol + Oxygen + Reduced adrenal ferredoxin + Hydrogen Ion → 20a,22b-Dihydroxycholesterol + Water + Oxidized adrenal ferredoxindetails