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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-06 13:52:37 UTC
Update Date2021-09-14 15:40:03 UTC
HMDB IDHMDB0006758
Secondary Accession Numbers
  • HMDB06758
Metabolite Identification
Common Name17a,21-Dihydroxy-5b-pregnane-3,11,20-trione
Description17alpha,21-Dihydroxy-5beta-pregnane-3,11,20-trione is an intermediate in C21-Steroid hormone metabolism. 17alpha,21-Dihydroxy-5beta-pregnane-3,11,20-trione is the second to last step in the synthesis of Cortolone and is converted. from Cortisone via the enzyme Delta4-3-oxosteroid 5beta-reductase (EC 1.3.1.3). It is then converted to Urocortisone via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50).
Structure
Data?1582752404
Synonyms
ValueSource
17alpha,21-Dihydroxy-5beta-pregnane-3,11,20-trioneChEBI
4,5beta-DihydrocortisoneChEBI
5-DihydrocortisoneChEBI
5beta-Pregnane-17alpha,21-diol-3,11,20-trioneChEBI
17Α,21-dihydroxy-5β-pregnane-3,11,20-trioneGenerator
4,5b-DihydrocortisoneGenerator
4,5Β-dihydrocortisoneGenerator
5b-Pregnane-17a,21-diol-3,11,20-trioneGenerator
5Β-pregnane-17α,21-diol-3,11,20-trioneGenerator
5 beta-DihydrocortisoneMeSH
5 beta-Pregnan-17 alpha,21-dihydroxy-3,11,20-trioneMeSH
17,21-Dihydroxy-5-beta-pregnane-3,11,20-trioneHMDB
17,21-Dihydroxy-5b-pregnane-3,11,20-trioneHMDB
4,5-b-DihydrocortisoneHMDB
4,5-beta-DihydrocortisoneHMDB
Chemical FormulaC21H30O5
Average Molecular Weight362.4599
Monoisotopic Molecular Weight362.20932407
IUPAC Name(1S,2S,7R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,17-dione
Traditional Namedihydrocortisone
CAS Registry Number68-54-2
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C21H30O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12,14-15,18,22,26H,3-11H2,1-2H3/t12-,14+,15+,18-,19+,20+,21+/m1/s1
InChI KeyYCLWEYIBFOLMEM-FNLRALKVSA-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-oxosteroid
  • 11-oxosteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • 3-oxo-5-beta-steroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Cyclic ketone
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • 4,5-dihydrocortisone (CHEBI:18093 )
  • C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C05469 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030095 )
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 Solubility0.13 g/LALOGPS
logP10(1.91) g/LALOGPS
logP10(1.71) g/LChemAxon
logS10(-3.4) g/LALOGPS
pKa (Strongest Acidic)12.58ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity95.65 m³·mol⁻¹ChemAxon
Polarizability39.44 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+185.50631661259
DarkChem[M-H]-181.70831661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,1TMS,#1C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO3301.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,1TMS,#2C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C3256.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,1TMS,#3C[C@]12CCC(=O)C[C@H]1CC[C@@H]1C2=C(O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO3150.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,1TMS,#4C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C3238.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,1TMS,#5C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2C(O[Si](C)(C)C)=C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO3132.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,1TMS,#6C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO3280.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,1TMS,#7C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO3272.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#1C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C3310.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#2C[C@]12CCC(=O)C[C@H]1CC[C@@H]1C2=C(O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO3126.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#3C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO3260.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#4C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO3277.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#5C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2C(O[Si](C)(C)C)=C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO3125.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#6C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C3261.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#7C[C@]12CCC(=O)C[C@H]1CC[C@@H]1C2=C(O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C3104.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#8C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C3235.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#9C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C3247.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#10C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2C(O[Si](C)(C)C)=C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C3070.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#11C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C3241.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#12C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1C2=C(O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO3084.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#13C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1C2=C(O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO3081.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#14C[C@]12CCC(=O)C[C@H]1CC[C@@H]1C2=C(O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C3046.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#15C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C3181.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#16C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C3199.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#17C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2C(O[Si](C)(C)C)=C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C3028.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#18C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1[C@@H]2C(O[Si](C)(C)C)=C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO3060.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TMS,#19C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2C(O[Si](C)(C)C)=C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO3069.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#1CC(C)(C)[Si](C)(C)O[C@]1(C(=O)CO)CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@@]21C3520.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#2CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@@]21C3530.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#3CC(C)(C)[Si](C)(C)OC1=C2[C@@H](CC[C@@H]3CC(=O)CC[C@]23C)[C@@H]2CC[C@](O)(C(=O)CO)[C@@]2(C)C13396.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#4CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@@]21C3477.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#5CC(C)(C)[Si](C)(C)OC1=C[C@@]2(C)[C@@H](CC[C@]2(O)C(=O)CO)[C@@H]2CC[C@@H]3CC(=O)CC[C@]3(C)[C@@H]123360.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#6CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3C(=O)C[C@@]4(C)[C@@H](CC[C@]4(O)C(=O)CO)[C@@H]3CC[C@@H]2C13523.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#7CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H](C(=O)C[C@@]4(C)[C@H]3CC[C@]4(O)C(=O)CO)[C@@]2(C)CC13511.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#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[C@@H]4CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@@]21C3785.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#2CC(C)(C)[Si](C)(C)OC1=C2[C@@H](CC[C@@H]3CC(=O)CC[C@]23C)[C@@H]2CC[C@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)[C@@]2(C)C13594.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#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[C@@H]4CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@@]21C3738.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#4CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3C(=O)C[C@@]4(C)[C@@H](CC[C@]4(O[Si](C)(C)C(C)(C)C)C(=O)CO)[C@@H]3CC[C@@H]2C13742.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#5CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H](C(=O)C[C@@]4(C)[C@H]3CC[C@]4(O[Si](C)(C)C(C)(C)C)C(=O)CO)[C@@]2(C)CC13726.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#6CC(C)(C)[Si](C)(C)OC1=C[C@@]2(C)[C@@H](CC[C@]2(O[Si](C)(C)C(C)(C)C)C(=O)CO)[C@@H]2CC[C@@H]3CC(=O)CC[C@]3(C)[C@@H]123571.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#7CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)C3=C(O[Si](C)(C)C(C)(C)C)C[C@@]21C3582.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#8CC(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[C@@H]4CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@@]21C3706.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#9CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3C(=O)C[C@@]21C3744.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#10CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C(=O)C[C@@]21C3722.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#11CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3C(O[Si](C)(C)C(C)(C)C)=C[C@@]21C3550.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#12CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)C3=C(O[Si](C)(C)C(C)(C)C)C[C@@]4(C)[C@@H](CC[C@]4(O)C(=O)CO)[C@@H]3CC[C@@H]2C13539.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#13CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3C(=C(O[Si](C)(C)C(C)(C)C)C[C@@]4(C)[C@H]3CC[C@]4(O)C(=O)CO)[C@@]2(C)CC13525.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#14CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)C3=C(O[Si](C)(C)C(C)(C)C)C[C@@]21C3502.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#15CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3C(=O)C[C@@]4(C)[C@@H](CC[C@]4(O)C(=CO)O[Si](C)(C)C(C)(C)C)[C@@H]3CC[C@@H]2C13672.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#16CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H](C(=O)C[C@@]4(C)[C@H]3CC[C@]4(O)C(=CO)O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC13649.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#17CC(C)(C)[Si](C)(C)OC1=C[C@@]2(C)[C@@H](CC[C@]2(O)C(=CO)O[Si](C)(C)C(C)(C)C)[C@@H]2CC[C@@H]3CC(=O)CC[C@]3(C)[C@@H]123471.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#18CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3C(O[Si](C)(C)C(C)(C)C)=C[C@@]4(C)[C@@H](CC[C@]4(O)C(=O)CO)[C@@H]3CC[C@@H]2C13530.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione,2TBDMS,#19CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H](C(O[Si](C)(C)C(C)(C)C)=C[C@@]4(C)[C@H]3CC[C@]4(O)C(=O)CO)[C@@]2(C)CC13510.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra
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 IDFDB024062
KNApSAcK IDNot Available
Chemspider ID58997
KEGG Compound IDC05469
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound65554
PDB IDNot Available
ChEBI ID18093
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 oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57
Reactions
Tetrahydrocortisone + NAD → 17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + NADH + Hydrogen Iondetails
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + Hydrogen Ion + NADPH → Tetrahydrocortisone + NADPdetails
General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
Reactions
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + NADP → Cortisonedetails
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + NADP → Cortisone + NADPH + Hydrogen Iondetails