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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:45 UTC
Update Date2021-09-14 15:40:02 UTC
HMDB IDHMDB0003259
Secondary Accession Numbers
  • HMDB0012460
  • HMDB03259
  • HMDB12460
Metabolite Identification
Common NameDihydrocortisol
DescriptionDihydrocortisol is the product of the enzyme steroid 5-beta-reductase (EC 1.3.1.3), which catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone, testosterone, aldosterone, corticosterone, and cortisol to 5-beta-reduced metabolites. A deficiency in this enzyme is associated with a congenital defect in bile acid synthesis (OMIM: 235555 ). Dihydrocortisol is the substrate of the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.225, 1.1.1.213, 1.3.1.20, 1.1.1.50), and is an intermediate in bile acid biosynthesis, C21-steroid hormone metabolism, androgen and estrogen metabolism, and the metabolism of xenobiotics by cytochrome P450 (KEGG).
Structure
Data?1584632605
Synonyms
ValueSource
(5beta,11beta)-11,17,21-Trihydroxypregnane-3,20-dioneChEBI
11-beta,17,21-Trihydroxy-5-beta-pregnane-3,20-dioneChEBI
5beta-Pregnane-11beta,17alpha,21-triol-3,20-dioneKegg
(5b,11b)-11,17,21-Trihydroxypregnane-3,20-dioneGenerator
(5Β,11β)-11,17,21-trihydroxypregnane-3,20-dioneGenerator
11-b,17,21-Trihydroxy-5-b-pregnane-3,20-dioneGenerator
11-Β,17,21-trihydroxy-5-β-pregnane-3,20-dioneGenerator
5b-Pregnane-11b,17a,21-triol-3,20-dioneGenerator
5Β-pregnane-11β,17α,21-triol-3,20-dioneGenerator
5-beta-DihydrocortisolHMDB
11beta,17,21-Trihydroxy-5beta-pregnane-3,20-dioneHMDB
11beta,17alpha,21-Trihydroxy-5beta-pregnane-3,20-dioneHMDB
11β,17,21-Trihydroxy-5β-pregnane-3,20-dioneHMDB
11β,17α,21-Trihydroxy-5β-pregnane-3,20-dioneHMDB
5beta-DihydrocortisolHMDB
5β-DihydrocortisolHMDB
DihydrocortisolHMDB
Chemical FormulaC21H32O5
Average Molecular Weight364.4758
Monoisotopic Molecular Weight364.224974134
IUPAC Name(1S,2S,7R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
Traditional Name(1S,2S,7R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
CAS Registry Number1482-50-4
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C21H32O5/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/h12,14-16,18,22,24,26H,3-11H2,1-2H3/t12-,14+,15+,16+,18-,19+,20+,21+/m1/s1
InChI KeyACSFOIGNUQUIGE-AIPUTVCKSA-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
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • 17-hydroxysteroid
  • 3-oxo-5-beta-steroid
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Cyclic ketone
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • 21-hydroxy steroid (CHEBI:732 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030204 )
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 Solubility0.22 g/LALOGPS
logP10(1.8) g/LALOGPS
logP10(1.32) g/LChemAxon
logS10(-3.2) g/LALOGPS
pKa (Strongest Acidic)12.58ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.57 m³·mol⁻¹ChemAxon
Polarizability40.1 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]+186.6431661259
DarkChem[M-H]-181.40631661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydrocortisol,1TMS,#1C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO3273.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,1TMS,#2C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C3212.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,1TMS,#3C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO3143.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,1TMS,#4C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C3175.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,1TMS,#5C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO3228.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,1TMS,#6C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO3210.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TMS,#1C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO3139.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TMS,#2C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C3283.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TMS,#3C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO3217.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TMS,#4C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO3236.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TMS,#5C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C3202.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TMS,#6C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C3096.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TMS,#7C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C3191.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TMS,#8C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C3210.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TMS,#9C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C3185.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TMS,#10C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO3082.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TMS,#11C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO3089.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TMS,#12C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C3062.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TMS,#13C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C3126.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TMS,#14C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C3141.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TMS,#1C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C3156.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TMS,#2C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO3116.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TMS,#3C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO3113.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TMS,#4C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C3104.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TMS,#5C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C3230.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TMS,#6C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C3251.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TMS,#7C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C3218.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TMS,#8C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C3156.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TMS,#9C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C3165.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TMS,#10C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C3088.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TMS,#11C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C3093.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TMS,#12C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C3071.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TMS,#13C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C3123.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TMS,#14C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C3140.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TMS,#15C[C@]12CCC(O[Si](C)(C)C)=C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C3043.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TMS,#16C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2[C@@H](O[Si](C)(C)C)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C3048.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,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]3[C@@H](O)C[C@@]21C3513.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,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]3[C@@H](O)C[C@@]21C3503.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,1TBDMS,#3CC(C)(C)[Si](C)(C)O[C@H]1C[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]123393.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,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]3[C@@H](O)C[C@@]21C3419.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,1TBDMS,#5CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3[C@@H](O)C[C@@]4(C)[C@@H](CC[C@]4(O)C(=O)CO)[C@@H]3CC[C@@H]2C13481.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,1TBDMS,#6CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H]([C@@H](O)C[C@@]4(C)[C@H]3CC[C@]4(O)C(=O)CO)[C@@]2(C)CC13455.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,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]3[C@@H](O)C[C@@]21C3779.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TBDMS,#2CC(C)(C)[Si](C)(C)O[C@H]1C[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]123598.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,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]3[C@@H](O)C[C@@]21C3691.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TBDMS,#4CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3[C@@H](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]2C13714.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TBDMS,#5CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H]([C@@H](O)C[C@@]4(C)[C@H]3CC[C@]4(O[Si](C)(C)C(C)(C)C)C(=O)CO)[C@@]2(C)CC13690.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TBDMS,#6CC(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]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3602.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TBDMS,#7CC(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]3[C@@H](O)C[C@@]21C3654.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TBDMS,#8CC(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]3[C@@H](O)C[C@@]21C3704.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TBDMS,#9CC(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]3[C@@H](O)C[C@@]21C3675.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TBDMS,#10CC(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]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3523.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TBDMS,#11CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3[C@@H](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]2C13551.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TBDMS,#12CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]4(C)[C@H]3CC[C@]4(O)C(=O)CO)[C@@]2(C)CC13539.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TBDMS,#13CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3[C@@H](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]2C13601.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,2TBDMS,#14CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H]([C@@H](O)C[C@@]4(C)[C@H]3CC[C@]4(O)C(=CO)O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC13575.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TBDMS,#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]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3844.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TBDMS,#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[C@@H]4CC(=O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3925.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TBDMS,#3CC(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[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3963.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TBDMS,#4CC(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]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3940.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TBDMS,#5CC(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]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3779.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TBDMS,#6CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)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]2C13763.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TBDMS,#7CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]4(C)[C@H]3CC[C@]4(O[Si](C)(C)C(C)(C)C)C(=O)CO)[C@@]2(C)CC13761.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TBDMS,#8CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3[C@@H](O)C[C@@]4(C)[C@@H](CC[C@]4(O[Si](C)(C)C(C)(C)C)C(=CO)O[Si](C)(C)C(C)(C)C)[C@@H]3CC[C@@H]2C13849.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TBDMS,#9CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H]([C@@H](O)C[C@@]4(C)[C@H]3CC[C@]4(O[Si](C)(C)C(C)(C)C)C(=CO)O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC13827.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TBDMS,#10CC(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]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3722.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TBDMS,#11CC(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]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3746.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TBDMS,#12CC(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]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3735.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TBDMS,#13CC(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[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3822.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TBDMS,#14CC(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]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3795.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TBDMS,#15CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)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]2C13699.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrocortisol,3TBDMS,#16CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]4(C)[C@H]3CC[C@]4(O)C(=CO)O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC13682.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrocortisol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ac0-3659000000-d401caa0e5e4cd33ce732017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrocortisol GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1501090000-2417a9d677690be1ebc92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrocortisol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrocortisol 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 - Dihydrocortisol 10V, Positive-QTOFsplash10-00kb-0009000000-1796f36bac594bc103ff2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocortisol 20V, Positive-QTOFsplash10-00p1-0139000000-132d9e769136246214032017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocortisol 40V, Positive-QTOFsplash10-052r-0392000000-6d131b6d30a3e0287a3a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocortisol 10V, Negative-QTOFsplash10-03di-0009000000-4cd88c3235f8488611a22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocortisol 20V, Negative-QTOFsplash10-0bta-2019000000-3c3c7ef5eaf1d99b90fb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocortisol 40V, Negative-QTOFsplash10-0a4i-9076000000-46fac6b742ffa35f0d092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocortisol 10V, Negative-QTOFsplash10-03di-0009000000-4a50053e3cc02927391e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocortisol 20V, Negative-QTOFsplash10-05o0-0009000000-aae740d9643ee587423a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocortisol 40V, Negative-QTOFsplash10-0udi-1039000000-f7ccd0c7e04c9e3097ca2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocortisol 10V, Positive-QTOFsplash10-014j-0009000000-266dd522a790c230d8da2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocortisol 20V, Positive-QTOFsplash10-02ta-0902000000-eaf773e5076582d8a12c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocortisol 40V, Positive-QTOFsplash10-03dm-8980000000-01a09a2f92bd6c0fa8ef2021-09-24Wishart 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 IDFDB023133
KNApSAcK IDNot Available
Chemspider ID144508
KEGG Compound IDC05471
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link5α-Dihydrocortisol
METLIN ID3173
PubChem Compound164838
PDB IDNot Available
ChEBI ID732
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. Heilmann P, Heide J, Hundertmark S, Schoneshofer M: Administration of glycyrrhetinic acid: significant correlation between serum levels and the cortisol/cortisone-ratio in serum and urine. Exp Clin Endocrinol Diabetes. 1999;107(6):370-8. [PubMed:10543414 ]
  2. Rivero-Marabe JJ, Maynar-Marino JI, Garcia-de-Tiedra MP, Galan-Martin AM, Caballero-Loscos MJ, Maynar-Marino M: Determination of natural corticosteroids in urine samples from sportsmen. J Chromatogr B Biomed Sci Appl. 2001 Sep 15;761(1):77-84. [PubMed:11585134 ]
  3. Schoneshofer M, Weber B, Nigam S: Increased urinary excretion of free 20 alpha- and 20 beta-dihydrocortisol in a hypercortisolemic but hypocortisoluric patient with Cushing's disease. Clin Chem. 1983 Feb;29(2):385-9. [PubMed:6821952 ]

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
Tetrahydrocortisol + NAD → Dihydrocortisol + NADH + Hydrogen Iondetails
Tetrahydrocortisol + NADP → Dihydrocortisol + NADPH + Hydrogen Iondetails
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
Dihydrocortisol + NADP → Cortisol + NADPH + Hydrogen Iondetails