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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:45 UTC
Update Date2017-10-23 19:04:02 UTC
HMDB IDHMDB0003259
Secondary Accession Numbers
  • 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 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 iintermediate in the Bile acid biosynthesis, C21-Steroid hormone metabolism, Androgen and estrogen metabolism, and in the Metabolism of xenobiotics by cytochrome P450. (KEGG).
Structure
Thumb
Synonyms
ValueSource
5beta-Pregnane-11beta,17alpha,21-triol-3,20-dioneKegg
5b-Pregnane-11b,17a,21-triol-3,20-dioneGenerator
5β-pregnane-11β,17α,21-triol-3,20-dioneGenerator
5-beta-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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
Traditional Namedihydrocortisol
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
DescriptionThis compound 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:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Industrial application:

Biological role:

  Molecular messenger:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP1.8ALOGPS
logP1.32ChemAxon
logS-3.2ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ac0-3659000000-d401caa0e5e4cd33ce73View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1501090000-2417a9d677690be1ebc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0009000000-1796f36bac594bc103ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00p1-0139000000-132d9e76913624621403View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-0392000000-6d131b6d30a3e0287a3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-4cd88c3235f8488611a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bta-2019000000-3c3c7ef5eaf1d99b90fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9076000000-46fac6b742ffa35f0d09View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
11-beta-hydroxylase deficiency (CYP11B1)Pw000551Pw000551 greyscalePw000551 simpleNot Available
17-alpha-hydroxylase deficiency (CYP17)Pw000542Pw000542 greyscalePw000542 simpleNot Available
21-hydroxylase deficiency (CYP21)Pw000552Pw000552 greyscalePw000552 simpleNot Available
3-Beta-Hydroxysteroid Dehydrogenase DeficiencyPw000695Pw000695 greyscalePw000695 simpleNot Available
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase DeficiencyPw000177Pw000177 greyscalePw000177 simpleNot Available
Displaying entries 1 - 5 of 11 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023133
KNApSAcK IDNot Available
Chemspider ID144508
KEGG Compound IDC05471
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3173
PubChem Compound164838
PDB IDNot Available
ChEBI 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 → Hydrocortisone + NADPH + Hydrogen Iondetails