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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-09-22 18:34:15 UTC
HMDB IDHMDB0000949
Secondary Accession Numbers
  • HMDB00949
Metabolite Identification
Common NameTetrahydrocortisol
DescriptionTetrahydrocortisol, also known as urocortisol, 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. Thus, tetrahydrocortisol is considered to be a steroid. Based on a literature review a significant number of articles have been published on Tetrahydrocortisol.
Structure
Data?1582752167
Synonyms
ValueSource
3alpha,5beta-TetrahydrocortisolChEBI
5beta-Pregnane-3alpha,11beta,17alpha,21-tetrol-20-oneChEBI
5beta-TetrahydrocortisolChEBI
TetrahydrohydrocortisoneChEBI
UrocortisolChEBI
3a,5b-TetrahydrocortisolGenerator
3Α,5β-tetrahydrocortisolGenerator
5b-Pregnane-3a,11b,17a,21-tetrol-20-oneGenerator
5Β-pregnane-3α,11β,17α,21-tetrol-20-oneGenerator
5b-TetrahydrocortisolGenerator
5Β-tetrahydrocortisolGenerator
2-Hydroxy-1-(3,11,17-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethanoneHMDB
3a,11b,17,21-Tetrahydroxy-5b-pregnan-20-oneHMDB
3b,11b,17,21-Tetrahydroxy-5b-pregnan-20-oneHMDB
3b,11b,17a,21-Tetrahydroxy-5b-pregnan-20-ONHMDB
DihydrocortisonHMDB
tetrahydro-CortisolHMDB
Chemical FormulaC21H34O5
Average Molecular Weight366.4917
Monoisotopic Molecular Weight366.240624198
IUPAC Name2-hydroxy-1-[(2S,5R,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one
Traditional Name2-hydroxy-1-[(2S,5R,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethanone
CAS Registry Number53-02-1
SMILES
C[C@]12C[C@H](O)C3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@]2(O)C(=O)CO
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+/m1/s1
InChI KeyAODPIQQILQLWGS-OBRSLYEHSA-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
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 Solubility0.47 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
Polarizability40.89 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]+185.40131661259
DarkChem[M-H]-179.78131661259
AllCCS[M+H]+191.66332859911
AllCCS[M-H]-193.26532859911
DeepCCS[M-2H]-226.50130932474
DeepCCS[M+Na]+202.06730932474
AllCCS[M+H]+191.732859911
AllCCS[M+H-H2O]+189.232859911
AllCCS[M+NH4]+194.032859911
AllCCS[M+Na]+194.632859911
AllCCS[M-H]-193.332859911
AllCCS[M+Na-2H]-193.932859911
AllCCS[M+HCOO]-194.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TetrahydrocortisolC[C@]12C[C@H](O)C3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@]2(O)C(=O)CO2549.9Standard polar33892256
TetrahydrocortisolC[C@]12C[C@H](O)C3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@]2(O)C(=O)CO3037.7Standard non polar33892256
TetrahydrocortisolC[C@]12C[C@H](O)C3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@]2(O)C(=O)CO3253.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tetrahydrocortisol,1TMS,isomer #1C[C@]12CC[C@@H](O)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O)C(=O)CO3267.2Semi standard non polar33892256
Tetrahydrocortisol,1TMS,isomer #2C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O)C[C@@]2(C)C1CC[C@]2(O)C(=O)CO3284.3Semi standard non polar33892256
Tetrahydrocortisol,1TMS,isomer #3C[C@]12CC[C@@H](O)CC1CCC1C2[C@@H](O)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=O)CO3312.6Semi standard non polar33892256
Tetrahydrocortisol,1TMS,isomer #4C[C@]12CC[C@@H](O)CC1CCC1C2[C@@H](O)C[C@@]2(C)C1CC[C@]2(O)C(=O)CO[Si](C)(C)C3280.7Semi standard non polar33892256
Tetrahydrocortisol,1TMS,isomer #5C[C@]12CC[C@@H](O)CC1CCC1C2[C@@H](O)C[C@@]2(C)C1CC[C@]2(O)C(=CO)O[Si](C)(C)C3220.1Semi standard non polar33892256
Tetrahydrocortisol,2TMS,isomer #1C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O)C(=O)CO3192.1Semi standard non polar33892256
Tetrahydrocortisol,2TMS,isomer #10C[C@]12CC[C@@H](O)CC1CCC1C2[C@@H](O)C[C@@]2(C)C1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C3240.4Semi standard non polar33892256
Tetrahydrocortisol,2TMS,isomer #2C[C@]12CC[C@@H](O)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=O)CO3218.5Semi standard non polar33892256
Tetrahydrocortisol,2TMS,isomer #3C[C@]12CC[C@@H](O)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O)C(=O)CO[Si](C)(C)C3218.4Semi standard non polar33892256
Tetrahydrocortisol,2TMS,isomer #4C[C@]12CC[C@@H](O)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O)C(=CO)O[Si](C)(C)C3131.8Semi standard non polar33892256
Tetrahydrocortisol,2TMS,isomer #5C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=O)CO3297.6Semi standard non polar33892256
Tetrahydrocortisol,2TMS,isomer #6C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O)C[C@@]2(C)C1CC[C@]2(O)C(=O)CO[Si](C)(C)C3295.5Semi standard non polar33892256
Tetrahydrocortisol,2TMS,isomer #7C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O)C[C@@]2(C)C1CC[C@]2(O)C(=CO)O[Si](C)(C)C3204.9Semi standard non polar33892256
Tetrahydrocortisol,2TMS,isomer #8C[C@]12CC[C@@H](O)CC1CCC1C2[C@@H](O)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C3330.3Semi standard non polar33892256
Tetrahydrocortisol,2TMS,isomer #9C[C@]12CC[C@@H](O)CC1CCC1C2[C@@H](O)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C3244.6Semi standard non polar33892256
Tetrahydrocortisol,3TMS,isomer #1C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=O)CO3180.1Semi standard non polar33892256
Tetrahydrocortisol,3TMS,isomer #10C[C@]12CC[C@@H](O)CC1CCC1C2[C@@H](O)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C3221.6Semi standard non polar33892256
Tetrahydrocortisol,3TMS,isomer #2C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O)C(=O)CO[Si](C)(C)C3196.7Semi standard non polar33892256
Tetrahydrocortisol,3TMS,isomer #3C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O)C(=CO)O[Si](C)(C)C3098.3Semi standard non polar33892256
Tetrahydrocortisol,3TMS,isomer #4C[C@]12CC[C@@H](O)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C3232.2Semi standard non polar33892256
Tetrahydrocortisol,3TMS,isomer #5C[C@]12CC[C@@H](O)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C3149.5Semi standard non polar33892256
Tetrahydrocortisol,3TMS,isomer #6C[C@]12CC[C@@H](O)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C3148.5Semi standard non polar33892256
Tetrahydrocortisol,3TMS,isomer #7C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C3283.7Semi standard non polar33892256
Tetrahydrocortisol,3TMS,isomer #8C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C3181.2Semi standard non polar33892256
Tetrahydrocortisol,3TMS,isomer #9C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O)C[C@@]2(C)C1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C3182.5Semi standard non polar33892256
Tetrahydrocortisol,4TMS,isomer #1C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C3220.7Semi standard non polar33892256
Tetrahydrocortisol,4TMS,isomer #2C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C3123.4Semi standard non polar33892256
Tetrahydrocortisol,4TMS,isomer #3C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C3125.1Semi standard non polar33892256
Tetrahydrocortisol,4TMS,isomer #4C[C@]12CC[C@@H](O)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C3175.6Semi standard non polar33892256
Tetrahydrocortisol,4TMS,isomer #5C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C3169.9Semi standard non polar33892256
Tetrahydrocortisol,5TMS,isomer #1C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C3116.6Semi standard non polar33892256
Tetrahydrocortisol,5TMS,isomer #1C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C3044.7Standard non polar33892256
Tetrahydrocortisol,5TMS,isomer #1C[C@]12CC[C@@H](O[Si](C)(C)C)CC1CCC1C2[C@@H](O[Si](C)(C)C)C[C@@]2(C)C1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C3352.9Standard polar33892256
Tetrahydrocortisol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C[C@@]2(C)C(CC[C@]2(O)C(=O)CO)C2CCC3C[C@H](O)CC[C@]3(C)C213518.1Semi standard non polar33892256
Tetrahydrocortisol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@@]2(C)C(CCC3C2[C@@H](O)C[C@@]2(C)C3CC[C@]2(O)C(=O)CO)C13526.1Semi standard non polar33892256
Tetrahydrocortisol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@]1(C(=O)CO)CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3[C@@H](O)C[C@@]21C3554.8Semi standard non polar33892256
Tetrahydrocortisol,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3[C@@H](O)C[C@@]21C3543.7Semi standard non polar33892256
Tetrahydrocortisol,1TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3[C@@H](O)C[C@@]21C3456.6Semi standard non polar33892256
Tetrahydrocortisol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C[C@@]2(C)C(CC[C@]2(O[Si](C)(C)C(C)(C)C)C(=O)CO)C2CCC3C[C@H](O)CC[C@]3(C)C213694.4Semi standard non polar33892256
Tetrahydrocortisol,2TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3[C@@H](O)C[C@@]21C3721.9Semi standard non polar33892256
Tetrahydrocortisol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3711.3Semi standard non polar33892256
Tetrahydrocortisol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1C[C@@]2(C)C(CC[C@]2(O)C(=O)CO)C2CCC3C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]3(C)C213661.8Semi standard non polar33892256
Tetrahydrocortisol,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3581.3Semi standard non polar33892256
Tetrahydrocortisol,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@@]2(C)C(CCC3C2[C@@H](O)C[C@@]2(C)C3CC[C@]2(O[Si](C)(C)C(C)(C)C)C(=O)CO)C13758.6Semi standard non polar33892256
Tetrahydrocortisol,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CCC2C3CCC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3[C@@H](O)C[C@@]21C3776.7Semi standard non polar33892256
Tetrahydrocortisol,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CCC2C3CCC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3[C@@H](O)C[C@@]21C3670.3Semi standard non polar33892256
Tetrahydrocortisol,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3[C@@H](O)C[C@@]21C3817.3Semi standard non polar33892256
Tetrahydrocortisol,2TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3[C@@H](O)C[C@@]21C3709.3Semi standard non polar33892256
Tetrahydrocortisol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3917.4Semi standard non polar33892256
Tetrahydrocortisol,3TBDMS,isomer #10CC(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)CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3[C@@H](O)C[C@@]21C3911.0Semi standard non polar33892256
Tetrahydrocortisol,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1C[C@@]2(C)C(CC[C@]2(O[Si](C)(C)C(C)(C)C)C(=O)CO)C2CCC3C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]3(C)C213847.3Semi standard non polar33892256
Tetrahydrocortisol,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3811.4Semi standard non polar33892256
Tetrahydrocortisol,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CCC2C3CCC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3843.0Semi standard non polar33892256
Tetrahydrocortisol,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3798.3Semi standard non polar33892256
Tetrahydrocortisol,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CCC2C3CCC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3770.8Semi standard non polar33892256
Tetrahydrocortisol,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3[C@@H](O)C[C@@]21C3988.7Semi standard non polar33892256
Tetrahydrocortisol,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3[C@@H](O)C[C@@]21C3871.1Semi standard non polar33892256
Tetrahydrocortisol,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CCC2C3CCC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3[C@@H](O)C[C@@]21C3883.2Semi standard non polar33892256
Tetrahydrocortisol,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C4065.0Semi standard non polar33892256
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)CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C4032.6Semi standard non polar33892256
Tetrahydrocortisol,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C4009.7Semi standard non polar33892256
Tetrahydrocortisol,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CCC2C3CCC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3987.8Semi standard non polar33892256
Tetrahydrocortisol,4TBDMS,isomer #5CC(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)CCC2C3CCC4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3[C@@H](O)C[C@@]21C4074.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000j-3539000000-bf3e8ad7a2d21593e6812017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (4 TMS) - 70eV, Positivesplash10-0fe3-1311189000-3a0cfdea998a0531cb8b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_3_5) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydrocortisol GC-MS (TMS_3_6) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrocortisol 10V, Positive-QTOFsplash10-0002-0019000000-5967aef805edb472d5a52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrocortisol 20V, Positive-QTOFsplash10-0532-0059000000-6e3db383f9bda6aa194a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrocortisol 40V, Positive-QTOFsplash10-01p9-1492000000-2266b6b18ef46f0eec052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrocortisol 10V, Negative-QTOFsplash10-014i-0009000000-5471dbe684b873e5784d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrocortisol 20V, Negative-QTOFsplash10-0ap1-2039000000-d95c86b33b8f11b833542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrocortisol 40V, Negative-QTOFsplash10-0a4i-9086000000-0e28c8ffdf44e3e921fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrocortisol 10V, Positive-QTOFsplash10-014i-0009000000-31730eb1a915ec83558e2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrocortisol 20V, Positive-QTOFsplash10-00kb-1926000000-49f68aeefa3e0ecff93e2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrocortisol 40V, Positive-QTOFsplash10-00mk-4930000000-ad7e5d12918fff3d04522021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrocortisol 10V, Negative-QTOFsplash10-014r-0009000000-599710d9e5fe39c6c2e82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrocortisol 20V, Negative-QTOFsplash10-066r-5009000000-934cc72c238c468a325b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydrocortisol 40V, Negative-QTOFsplash10-00kf-1079000000-515731aac544f36e01c82021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.19 (0.18-0.24) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.14 (0.086-0.17) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.21 +/- 0.038 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected and Quantified0.20 +/- 0.023 umol/mmol creatinineAdult (>18 years old)Female
Eating disorder
details
UrineDetected and Quantified0.62 +/- 0.085 umol/mmol creatinineAdult (>18 years old)Female
Eating disorder
details
UrineDetected and Quantified0.00024 +/- 0.00020 umol/mmol creatinineAdult (>18 years old)FemaleStress urinary incontinence details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5655
KEGG Compound IDC05472
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTetrahydrocortisol
METLIN IDNot Available
PubChem Compound5864
PDB IDNot Available
ChEBI ID28320
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceGould, David H.; Oliveto, Eugene P. 17a-Hydroxycorticosterone and intermediates. (1957), US 2783254 19570226 CAN 51:62564 AN 1957:62564
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Mune T, White PC: Apparent mineralocorticoid excess: genotype is correlated with biochemical phenotype. Hypertension. 1996 Jun;27(6):1193-9. [PubMed:8641723 ]
  3. 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 ]
  4. 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 ]
  5. Koren W, Grienspuhn A, Kuznetsov SR, Berezin M, Rosenthal T, Postnov YV: Enhanced Na+/H+ exchange in Cushing's syndrome reflects functional hypermineralocorticoidism. J Hypertens. 1998 Aug;16(8):1187-91. [PubMed:9794723 ]
  6. Rosler A, Leiberman E, Rosenmann A, Ben-Uzilio R, Weidenfeld J: Prenatal diagnosis of 11beta-hydroxylase deficiency congenital adrenal hyperplasia. J Clin Endocrinol Metab. 1979 Oct;49(4):546-51. [PubMed:314453 ]
  7. Melander O, Frandsen E, Groop L, Hulthen UL: No evidence of a relation between 11beta-hydroxysteroid dehydrogenase type 2 activity and salt sensitivity. Am J Hypertens. 2003 Sep;16(9 Pt 1):729-33. [PubMed:12944030 ]
  8. Quinkler M, Zehnder D, Lepenies J, Petrelli MD, Moore JS, Hughes SV, Cockwell P, Hewison M, Stewart PM: Expression of renal 11beta-hydroxysteroid dehydrogenase type 2 is decreased in patients with impaired renal function. Eur J Endocrinol. 2005 Aug;153(2):291-9. [PubMed:16061836 ]
  9. Rapetti S, Francia G, Iacono C, Martignoni G, Contessi G, Brunelli M, Galvanin F, Serio G: An unusual case of Cushing's syndrome due to ACTH-independent macronodular adrenal hyperplasia. Chir Ital. 2003 Mar-Apr;55(2):235-41. [PubMed:12744099 ]
  10. Panin LE, Tuzikov FV, Gimautdinova OI: Tetrahydrocortisol-apolipoprotein A-I complex specifically interacts with eukaryotic DNA and GCC elements of genes. J Steroid Biochem Mol Biol. 2003 Dec;87(4-5):309-18. [PubMed:14698212 ]

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