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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:03 UTC
HMDB IDHMDB0000526
Secondary Accession Numbers
  • HMDB00526
Metabolite Identification
Common Name5alpha-Tetrahydrocortisol
Description5alpha-Tetrahydrocortisol is a normal human metabolite. However its increased ratio (5alpha-tetrahydrocortisol + tetrahydrocortisol) over tetrahydrocortisone in urine is the biochemical marker for the syndrome of apparent mineralocorticoid excess (AME). AME is a heritable form of hypertension due to an inborn error of cortisol metabolism and is characterized by hypokalemia and low renin levels despite subnormal or normal levels of aldosterone and other known mineralocorticoids. The syndrome is attributable to congenital deficiency of the enzyme 11 beta-hydroxydehydrogenase (11-beta-HSD), which converts cortisol to biologically inactive cortisone. This results in a prolonged half-life of cortisol, which acts at the kidney level as a potent mineralocorticoid (PMID: 8732999 ).
Structure
Data?1582752137
Synonyms
ValueSource
5a-TetrahydrocortisolGenerator
5Α-tetrahydrocortisolGenerator
3,11,17,21-Tetrahydroxypregnan-20-oneHMDB
3a,11b,17,21-Tetrahydroxy-5a-pregnan-20-oneHMDB
3a,11b,17a,21-Tetrahydroxy-5a-pregnan-20-oneHMDB
3a,5a-TetrahydrocortisolHMDB
3a-AllotetrahydrocortisolHMDB
3alpha, 5alpha-TetrahydrocortisolHMDB
3alpha,5alpha-TetrahydrocortisolHMDB
5a-Pregnane-3a,11b,17a,21-tetraol-20-oneHMDB
5a-Pregnane-3a,11b,17a,21-tetrol-20-oneHMDB
a-THFHMDB
Allo-3a-tetrahydrocortisolHMDB
Allo-3alpha-tetrahydrocortisolHMDB
Allo-tetrahydrocortisolHMDB
Allopregnane-3a,11b,17a,21-tetrol-20-oneHMDB
Allopregnane-3a,11b,21-tetrol-20-oneHMDB
Allopregnane-3alpha,11beta,17alpha,21-tetrol-20-oneHMDB
Allotetrahydro-compound FHMDB
Allotetrahydro-cortisolHMDB
Allotetrahydrocompound FHMDB
AllotetrahydrocortisolHMDB
alpha-THFHMDB
ATHFHMDB
Kendall'S compound cHMDB
Reichstein'S substance CHMDB
Tetrahydro-allocortisolHMDB
TetrahydroallocortisolHMDB
Wintersteiner'S compound DHMDB
Allotetrahydrocortisol, (3beta,5alpha,11beta)-isomerHMDB
5AlphaTHFHMDB
Allotetrahydrocortisol, (3alpha,5beta,11alpha)-isomerHMDB
Allotetrahydrocortisol, (5alpha,11beta)-isomerHMDB
Allotetrahydrocortisol, (3beta,5beta,11beta)-isomerHMDB
(3alpha,5alpha,11beta)-3,11,17,21-Tetrahydroxypregnan-20-oneHMDB
(3Α,5α,11β)-3,11,17,21-tetrahydroxypregnan-20-oneHMDB
3alpha,11beta,17,21-Tetrahydroxy-5alpha-pregnan-20-oneHMDB
3alpha,11beta,17alpha,21-Tetrahydroxy-5alpha-pregnan-20-oneHMDB
3Α,11β,17,21-tetrahydroxy-5α-pregnan-20-oneHMDB
3Α,11β,17α,21-tetrahydroxy-5α-pregnan-20-oneHMDB
3Α,5α-tetrahydrocortisolHMDB
5alpha-Pregnane-3alpha,11beta,17alpha,21-tetraol-20-oneHMDB
5alpha-Pregnane-3alpha,11beta,17alpha,21-tetrol-20-oneHMDB
5alpha-THFHMDB
5Α-pregnane-3α,11β,17α,21-tetraol-20-oneHMDB
5Α-pregnane-3α,11β,17α,21-tetrol-20-oneHMDB
5Α-THFHMDB
Allopregnane-3α,11β,17α,21-tetrol-20-oneHMDB
Allo-3α-tetrahydrocortisolHMDB
Α-THFHMDB
5alpha-TetrahydrocortisolHMDB
Chemical FormulaC21H34O5
Average Molecular Weight366.4917
Monoisotopic Molecular Weight366.240624198
IUPAC Name2-hydroxy-1-[(1S,2S,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one
Traditional Name2-hydroxy-1-[(1S,2S,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone
CAS Registry Number302-91-0
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])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H34O5/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/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18+,19-,20-,21-/m0/s1
InChI KeyAODPIQQILQLWGS-FDSHTENPSA-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-hydroxysteroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 17-hydroxysteroid
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Polyol
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030200 )
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point244.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
logP1.38ALOGPS
logP1.11ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)12.58ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity97.6 m³·mol⁻¹ChemAxon
Polarizability41.32 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]+188.3231661259
DarkChem[M-H]-182.52531661259
AllCCS[M+H]+191.11132859911
AllCCS[M-H]-193.26532859911
DeepCCS[M-2H]-219.81930932474
DeepCCS[M+Na]+194.05230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5alpha-Tetrahydrocortisol[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])C[C@H](O)CC[C@]12C2744.5Standard polar33892256
5alpha-Tetrahydrocortisol[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])C[C@H](O)CC[C@]12C3136.9Standard non polar33892256
5alpha-Tetrahydrocortisol[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])C[C@H](O)CC[C@]12C3281.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5alpha-Tetrahydrocortisol,1TMS,isomer #1C[C@]12CC[C@@H](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)CO3241.4Semi standard non polar33892256
5alpha-Tetrahydrocortisol,1TMS,isomer #2C[C@]12CC[C@@H](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)C3187.9Semi standard non polar33892256
5alpha-Tetrahydrocortisol,1TMS,isomer #3C[C@]12CC[C@@H](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)CO3127.6Semi standard non polar33892256
5alpha-Tetrahydrocortisol,1TMS,isomer #4C[C@]12CC[C@@H](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)CO3205.2Semi standard non polar33892256
5alpha-Tetrahydrocortisol,1TMS,isomer #5C[C@]12CC[C@@H](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)C3152.1Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TMS,isomer #1C[C@]12CC[C@@H](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)CO3208.7Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TMS,isomer #10C[C@]12CC[C@@H](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)C3111.6Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TMS,isomer #2C[C@]12CC[C@@H](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)CO3115.0Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TMS,isomer #3C[C@]12CC[C@@H](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)C3252.2Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TMS,isomer #4C[C@]12CC[C@@H](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)C3170.0Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TMS,isomer #5C[C@]12CC[C@@H](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)C3182.9Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TMS,isomer #6C[C@]12CC[C@@H](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)C3088.8Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TMS,isomer #7C[C@]12CC[C@@H](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)C3151.4Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TMS,isomer #8C[C@]12CC[C@@H](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)CO3062.5Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TMS,isomer #9C[C@]12CC[C@@H](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)C3050.3Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TMS,isomer #1C[C@]12CC[C@@H](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)CO3099.3Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TMS,isomer #10C[C@]12CC[C@@H](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)C3021.8Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TMS,isomer #2C[C@]12CC[C@@H](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)C3217.6Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TMS,isomer #3C[C@]12CC[C@@H](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)C3125.0Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TMS,isomer #4C[C@]12CC[C@@H](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)C3138.6Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TMS,isomer #5C[C@]12CC[C@@H](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)C3074.1Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TMS,isomer #6C[C@]12CC[C@@H](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)C3187.6Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TMS,isomer #7C[C@]12CC[C@@H](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)C3070.1Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TMS,isomer #8C[C@]12CC[C@@H](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)C3108.6Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TMS,isomer #9C[C@]12CC[C@@H](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)C3054.6Semi standard non polar33892256
5alpha-Tetrahydrocortisol,4TMS,isomer #1C[C@]12CC[C@@H](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)CO[Si](C)(C)C3136.3Semi standard non polar33892256
5alpha-Tetrahydrocortisol,4TMS,isomer #2C[C@]12CC[C@@H](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(=CO)O[Si](C)(C)C3068.9Semi standard non polar33892256
5alpha-Tetrahydrocortisol,4TMS,isomer #3C[C@]12CC[C@@H](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[Si](C)(C)C)O[Si](C)(C)C3154.4Semi standard non polar33892256
5alpha-Tetrahydrocortisol,4TMS,isomer #4C[C@]12CC[C@@H](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[Si](C)(C)C)O[Si](C)(C)C3111.0Semi standard non polar33892256
5alpha-Tetrahydrocortisol,4TMS,isomer #5C[C@]12CC[C@@H](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[Si](C)(C)C)O[Si](C)(C)C3040.2Semi standard non polar33892256
5alpha-Tetrahydrocortisol,5TMS,isomer #1C[C@]12CC[C@@H](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(=CO[Si](C)(C)C)O[Si](C)(C)C3092.9Semi standard non polar33892256
5alpha-Tetrahydrocortisol,5TMS,isomer #1C[C@]12CC[C@@H](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(=CO[Si](C)(C)C)O[Si](C)(C)C3097.9Standard non polar33892256
5alpha-Tetrahydrocortisol,5TMS,isomer #1C[C@]12CC[C@@H](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(=CO[Si](C)(C)C)O[Si](C)(C)C3333.8Standard polar33892256
5alpha-Tetrahydrocortisol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@]1(C(=O)CO)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3496.9Semi standard non polar33892256
5alpha-Tetrahydrocortisol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3472.2Semi standard non polar33892256
5alpha-Tetrahydrocortisol,1TBDMS,isomer #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]3C[C@H](O)CC[C@]3(C)[C@@H]123380.9Semi standard non polar33892256
5alpha-Tetrahydrocortisol,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]3CC[C@]2(O)C(=O)CO)C13451.3Semi standard non polar33892256
5alpha-Tetrahydrocortisol,1TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3388.7Semi standard non polar33892256
5alpha-Tetrahydrocortisol,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[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3755.2Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3575.2Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]3CC[C@]2(O[Si](C)(C)C(C)(C)C)C(=O)CO)C13690.1Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TBDMS,isomer #3CC(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]3C[C@H](O)CC[C@]3(C)[C@@H]123591.6Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TBDMS,isomer #4CC(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]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3644.0Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3684.2Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3590.8Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TBDMS,isomer #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]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3622.3Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TBDMS,isomer #8CC(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]3C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]3(C)[C@@H]123524.5Semi standard non polar33892256
5alpha-Tetrahydrocortisol,2TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3499.5Semi standard non polar33892256
5alpha-Tetrahydrocortisol,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[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3952.6Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](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@@]21C3675.8Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TBDMS,isomer #2CC(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@H](O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3832.4Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TBDMS,isomer #3CC(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]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3880.0Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TBDMS,isomer #4CC(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]3C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]3(C)[C@@H]123752.5Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TBDMS,isomer #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]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3830.5Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TBDMS,isomer #6CC(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]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3753.3Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@H](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@@]21C3733.7Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TBDMS,isomer #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]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C3805.4Semi standard non polar33892256
5alpha-Tetrahydrocortisol,3TBDMS,isomer #9CC(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@H](O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3721.8Semi standard non polar33892256
5alpha-Tetrahydrocortisol,4TBDMS,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[C@H]4C[C@H](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@@]21C3978.6Semi standard non polar33892256
5alpha-Tetrahydrocortisol,4TBDMS,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[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C4074.6Semi standard non polar33892256
5alpha-Tetrahydrocortisol,4TBDMS,isomer #3CC(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]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3968.4Semi standard non polar33892256
5alpha-Tetrahydrocortisol,4TBDMS,isomer #4CC(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]4C[C@H](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@@]21C3934.2Semi standard non polar33892256
5alpha-Tetrahydrocortisol,4TBDMS,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[C@H]4C[C@H](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@@]21C3875.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000j-3539000000-d7581fc3650c2eb0185b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (4 TMS) - 70eV, Positivesplash10-000l-1200139000-f34c6af9d49af972f03b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_3_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_3_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Tetrahydrocortisol GC-MS (TMS_3_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 10V, Positive-QTOFsplash10-0002-0019000000-5967aef805edb472d5a52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 20V, Positive-QTOFsplash10-0532-0059000000-6e3db383f9bda6aa194a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 40V, Positive-QTOFsplash10-01p9-1492000000-2266b6b18ef46f0eec052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 10V, Negative-QTOFsplash10-014i-0009000000-5471dbe684b873e5784d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 20V, Negative-QTOFsplash10-0ap1-2039000000-d95c86b33b8f11b833542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 40V, Negative-QTOFsplash10-0a4i-9086000000-0e28c8ffdf44e3e921fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 10V, Negative-QTOFsplash10-014i-0009000000-8339b94cd560c336a8d42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 20V, Negative-QTOFsplash10-014i-2009000000-76e08d0eac5051f615bf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 40V, Negative-QTOFsplash10-100c-0039000000-af1a66b3967a8f31e2d42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 10V, Positive-QTOFsplash10-015a-0009000000-249d6f44172a375b08be2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 20V, Positive-QTOFsplash10-014i-1902000000-95c98bcfe0691617e5b52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Tetrahydrocortisol 40V, Positive-QTOFsplash10-00kb-8980000000-ea48ab8fad3384d8e0c62021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.14 (0.10-0.16) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.071 (0.048-0.095) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.19 +/- 0.026 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.023 +/- 0.009 uMAdult (>18 years old)BothAnorexia nervosa details
UrineDetected and Quantified0.13 +/- 0.029 umol/mmol creatinineAdult (>18 years old)Female
Eating disorder
details
UrineDetected and Quantified0.65 +/- 0.14 umol/mmol creatinineAdult (>18 years old)Female
Eating disorder
details
Associated Disorders and Diseases
Disease References
Anorexia nervosa
  1. Vierhapper H, Kiss A, Nowotny P, Wiesnagrotzki S, Monder C, Waldhausl W: Metabolism of cortisol in anorexia nervosa. Acta Endocrinol (Copenh). 1990 Jun;122(6):753-8. [PubMed:2165347 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022094
KNApSAcK IDNot Available
Chemspider ID83726
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5511
PubChem Compound92748
PDB IDNot Available
ChEBI ID89627
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceFukushima, David K.; Daum, Sol. Synthesis of Reichstein's substance C and related compounds. Journal of Organic Chemistry (1961), 26 520-3.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
  2. Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17. [PubMed:14625002 ]
  3. Mune T, White PC: Apparent mineralocorticoid excess: genotype is correlated with biochemical phenotype. Hypertension. 1996 Jun;27(6):1193-9. [PubMed:8641723 ]
  4. Weykamp CW, Penders TJ, Schmidt NA, Borburgh AJ, van de Calseyde JF, Wolthers BJ: Steroid profile for urine: reference values. Clin Chem. 1989 Dec;35(12):2281-4. [PubMed:2591044 ]
  5. Kerstens MN, van der Kleij FG, Boonstra AH, Sluiter WJ, van der Molen JC, Navis G, Dullaart RP: Angiotensin administration stimulates renal 11 beta-hydroxysteroid dehydrogenase activity in healthy men. Kidney Int. 2004 Jun;65(6):2065-70. [PubMed:15149319 ]
  6. Mantero F, Palermo M, Petrelli MD, Tedde R, Stewart PM, Shackleton CH: Apparent mineralocorticoid excess: type I and type II. Steroids. 1996 Apr;61(4):193-6. [PubMed:8732999 ]