Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-06 15:31:56 UTC
Update Date2022-03-07 02:49:33 UTC
HMDB IDHMDB0006762
Secondary Accession Numbers
  • HMDB0000382
  • HMDB00382
  • HMDB06762
Metabolite Identification
Common Name17alpha,21-Dihydroxypregnenolone
Description17alpha,21-Dihydroxypregnenolone is an intermediate in the human fetus at midpregnancy that is converted into cortisol (PMID: 4231965 ). It has also been found as an intermediate in alternative pathways in human adrenal steroidogenesis that take place under in vitro conditions. In normal adrenal slices from patients with hypernephroid kidney carcinomas these pathways bypass cholesterol, pregnenolone, and progesterone, and proceed to 21-hydroxypregnenolone (PMID: 6247575 ). 17alpha,21-Dihydroxypregnenolone is an intermediate in C21-Steroid hormone metabolism. 17alpha,21-Dihydroxypregnenolone is the 5th to last step in the synthesis of Cortol and is converted from 17alpha-Hydroxypregnenolone via the enzyme cytochrome P450 (EC 1.14.99.10). It is then converted to 11beta,17alpha,21-Trihydroxypregnenolone via the enzyme cytochrome P450 (EC 1.14.15.4).
Structure
Data?1582752404
Synonyms
ValueSource
17a,21-DihydroxypregnenoloneGenerator
17Α,21-dihydroxypregnenoloneGenerator
17alpha,21-Dihydroxypreg-nenoloneHMDB
17, 21-DihydroxypregnenoloneHMDB
3Β,17α,21-trihydroxypregnenoneHMDB
3beta,17alpha,21-TrihydroxypregnenoneHMDB
17,21-DihydroxypregnenoloneHMDB
3Β,17,21-trihydroxy-pregn-5-en-20-oneHMDB
3beta,17,21-Trihydroxy-pregn-5-en-20-oneHMDB
(3Β)-3,17,21-trihydroxypregn-5-en-20-oneHMDB
(3beta)-3,17,21-Trihydroxypregn-5-en-20-oneHMDB
3Β,17α,21-trihydroxypregn-5-en-20-oneHMDB
3beta,17alpha,21-Trihydroxypregn-5-en-20-oneHMDB
17alpha,21-DihydroxypregnenoloneHMDB
Chemical FormulaC21H32O4
Average Molecular Weight348.4764
Monoisotopic Molecular Weight348.230059512
IUPAC Name1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-hydroxyethan-1-one
Traditional Name1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-hydroxyethanone
CAS Registry Number1167-48-2
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H32O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h3,14-17,22-23,25H,4-12H2,1-2H3/t14-,15+,16-,17-,19-,20-,21-/m0/s1
InChI KeyJNHJGXQUDOYJAK-IYRCEVNGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 21-hydroxysteroid
  • 20-oxosteroid
  • Pregnane-skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Oxosteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • 17-hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
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 Solubility0.057 g/LALOGPS
logP2.6ALOGPS
logP2.02ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)12.59ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.86 m³·mol⁻¹ChemAxon
Polarizability39.63 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+184.42631661259
DarkChem[M-H]-178.70731661259
DeepCCS[M-2H]-214.11130932474
DeepCCS[M+Na]+188.57430932474
AllCCS[M+H]+187.932859911
AllCCS[M+H-H2O]+185.232859911
AllCCS[M+NH4]+190.432859911
AllCCS[M+Na]+191.132859911
AllCCS[M-H]-190.432859911
AllCCS[M+Na-2H]-190.932859911
AllCCS[M+HCOO]-191.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
17alpha,21-Dihydroxypregnenolone[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C2603.6Standard polar33892256
17alpha,21-Dihydroxypregnenolone[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C2925.1Standard non polar33892256
17alpha,21-Dihydroxypregnenolone[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C3063.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
17alpha,21-Dihydroxypregnenolone,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO3144.2Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C3112.6Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=O)CO3124.5Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,1TMS,isomer #4C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C3025.5Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO3161.0Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,2TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C3193.6Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,2TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C3100.1Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,2TMS,isomer #4C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C3146.0Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,2TMS,isomer #5C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C3072.8Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,2TMS,isomer #6C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C3033.9Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,3TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C3201.1Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,3TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C3097.9Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,3TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C3185.0Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,3TMS,isomer #4C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C3078.4Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,4TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C3156.8Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,4TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C3077.0Standard non polar33892256
17alpha,21-Dihydroxypregnenolone,4TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C3356.9Standard polar33892256
17alpha,21-Dihydroxypregnenolone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@]1(C(=O)CO)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3409.7Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3413.4Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@](O)(C(=O)CO)[C@@]4(C)CC[C@@H]32)C13388.7Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3307.6Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3745.2Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)[C@@]4(C)CC[C@@H]32)C13679.4Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3647.4Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3688.8Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3607.0Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3544.7Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3960.4Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3959.8Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3852.1Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3818.4Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4117.6Semi standard non polar33892256
17alpha,21-Dihydroxypregnenolone,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3892.6Standard non polar33892256
17alpha,21-Dihydroxypregnenolone,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3619.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 17alpha,21-Dihydroxypregnenolone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lr-4189000000-38652a1384b510a4e8492017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17alpha,21-Dihydroxypregnenolone GC-MS (3 TMS) - 70eV, Positivesplash10-0f6t-1111090000-ac64327581e7c755d2852017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17alpha,21-Dihydroxypregnenolone 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 - 17alpha,21-Dihydroxypregnenolone 10V, Positive-QTOFsplash10-001j-0029000000-0868a1856a2a865dc2da2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 20V, Positive-QTOFsplash10-01qa-0097000000-873e4eef53be76546e5f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 40V, Positive-QTOFsplash10-00xr-0491000000-bf3679c3178ebe5ceb4e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 10V, Negative-QTOFsplash10-0002-0029000000-5f642a89fae11d677fda2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 20V, Negative-QTOFsplash10-05bs-3098000000-d61819020861e0a89cf52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 40V, Negative-QTOFsplash10-0a4i-6091000000-8a9828ddf7d9d4a69ef62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 10V, Negative-QTOFsplash10-0002-0019000000-b815dac004fdf0d569442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 20V, Negative-QTOFsplash10-00kk-1096000000-5d0fda6d923e4716d9862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 40V, Negative-QTOFsplash10-000i-0090000000-a4cb9cce30a71598a7612021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 10V, Positive-QTOFsplash10-0002-0009000000-4e7f285caeb4129cd7062021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 20V, Positive-QTOFsplash10-01xw-0911000000-08a13dee014c9e27e8d32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 40V, Positive-QTOFsplash10-00os-2930000000-32c88edb904f52d771582021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB024065
KNApSAcK IDNot Available
Chemspider ID167253
KEGG Compound IDC05487
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound192735
PDB IDNot Available
ChEBI ID27832
Food Biomarker OntologyNot Available
VMH IDM00406
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHeer, J.; Miescher, K. Steroids. CIV. The synthesis of the dihydroxyacetone side chain in the steroid series. Helvetica Chimica Acta (1951), 34 359-72.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pasqualini JR, Lowy J, Wiqvist N, Diczfalusy E: Biosynthesis of cortisol from 3 beta, 17 alpha,21-trihydroxypregn-5-en-20-one by the intact human foetus at midpregnancy. Biochim Biophys Acta. 1968 May 1;152(3):648-50. [PubMed:4231965 ]
  2. Kaufmann SH, Sinterhauf K, Lommer D: Alternative pathways in human corticosteroid biosynthesis. J Steroid Biochem. 1980 Jun;13(6):599-605. [PubMed:6247575 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:
CYP11B1
Uniprot ID:
P15538
Molecular weight:
57572.44
Reactions
17alpha,21-Dihydroxypregnenolone + Reduced ferredoxin + Oxygen → 11b,17a,21-Trihydroxypreg-nenolone + Oxidized ferredoxin + Waterdetails
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. Efficiently catalyzes the transformation of pregnenolone to progesterone, 17-alpha-hydroxypregnenolone to 17-alpha-hydroxyprogesterone, DHEA to 4-androstenedione, dihydrotestosterone to 5-alpha-androstane-3 beta,17 beta-diol, dehydroepiandrosterone to androstenedione and 5-alpha-androstan-3 beta,17 beta-diol to 5-alpha-dihydrotestosterone.
Gene Name:
HSD3B1
Uniprot ID:
P14060
Molecular weight:
42251.25
Reactions
Cortexolone + Hydrogen Ion + NADH → 17alpha,21-Dihydroxypregnenolone + NADdetails
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:
HSD3B2
Uniprot ID:
P26439
Molecular weight:
42051.845
Reactions
Cortexolone + Hydrogen Ion + NADH → 17alpha,21-Dihydroxypregnenolone + NADdetails
General function:
Involved in monooxygenase activity
Specific function:
Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name:
CYP11B2
Uniprot ID:
P19099
Molecular weight:
57559.62
Reactions
17alpha,21-Dihydroxypregnenolone + Reduced ferredoxin + Oxygen → 11b,17a,21-Trihydroxypreg-nenolone + Oxidized ferredoxin + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
P450-CYP21B
Uniprot ID:
Q16874
Molecular weight:
56000.9
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP21A2
Uniprot ID:
Q08AG9
Molecular weight:
55972.9
General function:
Not Available
Specific function:
Specifically catalyzes the 21-hydroxylation of steroids. Required for the adrenal synthesis of mineralocorticoids and glucocorticoids.
Gene Name:
CYP21A2
Uniprot ID:
P08686
Molecular weight:
56000.94
Reactions
17a-Hydroxypregnenolone + NADPH + Hydrogen Ion + Oxygen → 17alpha,21-Dihydroxypregnenolone + NADP + Waterdetails