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Showing metabocard for Tetrahydrocortisol (HMDB0000949)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:47 UTC
HMDB IDHMDB0000949
Secondary Accession Numbers
  • HMDB00949
Metabolite Identification
Common NameTetrahydrocortisol
DescriptionTaurochenodesoxycholic acid, also known as chenodeoxycholoyltaurine or taurine chenodeoxycholate, belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety. Taurochenodesoxycholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752167
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Taurochenodeoxycholic acidKegg
ChenodeoxycholoyltaurineKegg
TaurochenodeoxycholateGenerator
TaurochenodesoxycholateGenerator
Taurine chenodeoxycholateHMDB
Taurine chenodeoxycholic acidHMDB
12-DeoxycholyltaurineHMDB
12-DesoxycholyltaurineHMDB
3a,7a-Dihydroxy-N-(2-sulfoethyl)-5b-cholan-24-amideHMDB
ChenodeoxycholyltaurineHMDB
ChenyltaurineHMDB
N-(3a,7a-Dihydroxy-5b-cholan-24-oyl)-taurineHMDB
Acid, taurochenodeoxycholicHMDB
Chenodeoxycholate, taurineHMDB
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
5b-TetrahydrocortisolHMDB
DihydrocortisonHMDB
tetrahydro-CortisolHMDB
UrocortisolHMDB
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 taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTaurinated bile acids and derivatives
Alternative Parents
Substituents
  • Taurinated bile acid
  • Dihydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Fatty acyl
  • Fatty amide
  • N-acyl-amine
  • Alkanesulfonic acid
  • Cyclic alcohol
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Sulfonyl
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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 Solubility0.47 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000j-3539000000-bf3e8ad7a2d21593e681Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0fe3-1311189000-3a0cfdea998a0531cb8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0019000000-5967aef805edb472d5a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0532-0059000000-6e3db383f9bda6aa194aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1492000000-2266b6b18ef46f0eec05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-5471dbe684b873e5784dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ap1-2039000000-d95c86b33b8f11b83354Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9086000000-0e28c8ffdf44e3e921feSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • 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
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 IDDB08833
Phenol Explorer Compound IDNot Available
FooDB IDFDB022335
KNApSAcK IDNot Available
Chemspider ID343282
KEGG Compound IDC05465
BioCyc IDCHENODEOXYCHOLOYLTAURINE
BiGG ID45864
Wikipedia LinkNot Available
METLIN ID5897
PubChem Compound387316
PDB IDNot Available
ChEBI ID16525
Food Biomarker OntologyNot Available
VMH IDTDCHOLA
MarkerDB ID
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. Mune T, White PC: Apparent mineralocorticoid excess: genotype is correlated with biochemical phenotype. Hypertension. 1996 Jun;27(6):1193-9. [PubMed:8641723 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  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. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]

Enzymes

Enzyme Details
1. Aldo-keto reductase family 1 member C4
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