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Human Metabolome Database Version 2.5

 

Showing metabocard for Tetrahydrocortisol (HMDB00949)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2009-08-04 14:48:33
Accession Number HMDB00949
Secondary Accession Numbers Not Available
Common Name Tetrahydrocortisol
Description Tetrahydrocortisol is the most powerful natural angiostatic steroid. It is involved in C21-Steroid hormone metabolism pathway (KEGG).
Synonyms
  1. 2-hydroxy-1-(3,11,17-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethanone
  2. 3a,11b,17,21-tetrahydroxy-5b-pregnan-20-one
  3. 3b,11b,17,21-tetrahydroxy-5b-pregnan-20-one
  4. 3b,11b,17a,21-Tetrahydroxy-5b-pregnan-20-on
  5. Dihydrocortison
  6. Tetrahydro-cortisol
  7. Tetrahydrocortisol
  8. Urocortisol
  9. 5b-Tetrahydrocortisol
Chemical IUPAC Name 2-hydroxy-1-(3,11,17-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-yl)-ethanone
Chemical Formula C21H34O5
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Ketosteroids
Family
  • Mammalian Metabolite
Species
  • ketone
  • primary alcohol
  • secondary alcohol
  • tertiary alcohol
Biofunction
  • Hormones, Membrane component
Application
—
Source
  • Endogenous
Average Molecular Weight 366.492
Monoisotopic Molecular Weight 366.240631
Isomeric SMILES C[C@]12CC[C@@H](O)CC1CCC1C3CC[C@](O)(C(=O)CO)[C@@]3(C)C[C@H](O)C21
Canonical SMILES CC12CCC(O)CC1CCC1C3CCC(O)(C(=O)CO)C3(C)CC(O)C21
KEGG Compound ID C05472 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00949 Link Image
Metagene Link HMDB00949 Link Image
METLIN ID 1914 Link Image
PubChem Compound 5864 Link Image
PubChem Substance 841399 Link Image
ChEBI ID Not Available
CAS Registry Number 53-02-1
InChI Identifier InChI=1/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
Synthesis Reference Gould, David H.; Oliveto, Eugene P. 17a-Hydroxycorticosterone and intermediates. (1957), US 2783254 19570226 CAN 51:62564 AN 1957:62564
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.466 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 1.38 [Predicted by ALOGPS]; 1.8 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location
  • Urine
Tissue Location Not Available
Concentrations (Normal)
Biofluid Urine
Value 0.21 +/- 0.038 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Female
Patient information Normal
Comments Not Available
References
  • Poor V, Biro I, Bufa A, Gati A, Fenyvesi I, Juricskay S, Tenyi T, Kilar F: Urinary steroids in young women with eating disorders. J Biochem Biophys Methods. 2004 Oct 29;61(1-2):199-205. [PubMed Link Image]
Biofluid Urine
Value 0.19 (0.18-0.24) umol/mmol creatinine
Age Adult:>18 yrs old
Sex Male
Patient information Normal
Comments Not Available
References
  • Shamim W, Yousufuddin M, Bakhai A, Coats AJ, Honour JW: Gender differences in the urinary excretion rates of cortisol and androgen metabolites. Ann Clin Biochem. 2000 Nov;37 ( Pt 6):770-4. [PubMed Link Image]
Biofluid Urine
Value 0.14 (0.086-0.17) umol/mmol creatinine
Age Adult:>18 yrs old
Sex Female
Patient information Normal
Comments Not Available
References
  • Shamim W, Yousufuddin M, Bakhai A, Coats AJ, Honour JW: Gender differences in the urinary excretion rates of cortisol and androgen metabolites. Ann Clin Biochem. 2000 Nov;37 ( Pt 6):770-4. [PubMed Link Image]
Concentrations (Abnormal)
Biofluid Urine
Value 0.20 +/- 0.023 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Female
Comments Eating disorders: anorexia nervosa, bulimia nervosa and bulimarexia Subgroup I: low Cortisol metabolites level
References
  • Poor V, Biro I, Bufa A, Gati A, Fenyvesi I, Juricskay S, Tenyi T, Kilar F: Urinary steroids in young women with eating disorders. J Biochem Biophys Methods. 2004 Oct 29;61(1-2):199-205. [PubMed Link Image]
Biofluid Urine
Value 0.62 +/- 0.085 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Female
Comments Eating disorders: anorexia nervosa, bulimia nervosa and bulimarexia Subgroup II: High Cortisol metabolites level
References
  • Poor V, Biro I, Bufa A, Gati A, Fenyvesi I, Juricskay S, Tenyi T, Kilar F: Urinary steroids in young women with eating disorders. J Biochem Biophys Methods. 2004 Oct 29;61(1-2):199-205. [PubMed Link Image]
Biofluid Urine
Value 0.00024 +/- 0.00020 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Female
Comments Not Available
References
  • Bai SW, Jung BH, Chung BC, Kim SU, Kim JY, Rha KH, Cho JS, Park YW, Park KH: Relationship between urinary profile of the endogenous steroids and postmenopausal women with stress urinary incontinence. Neurourol Urodyn. 2003;22(3):198-205. [PubMed Link Image]
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Steroidogenesis SMP00130 Link Image map00140 Link Image
General References
  1. Mune T, White PC: Apparent mineralocorticoid excess: genotype is correlated with biochemical phenotype. Hypertension. 1996 Jun;27(6):1193-9. [PubMed Link Image]
  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 Link Image]
  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 Link Image]
  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 Link Image]
  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 Link Image]
  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 Link Image]
  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 Link Image]
  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 Link Image]
  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 Link Image]
  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 Link Image]
Metabolic Enzymes
  1. Aldo-keto reductase family 1 member C4
Enzyme 1 [top]
Enzyme 1 ID 5303
Enzyme 1 Name Aldo-keto reductase family 1 member C4
Enzyme 1 Synonyms
  1. Chlordecone reductase
  2. CDR
  3. 3-alpha-hydroxysteroid dehydrogenase type I
  4. 3-alpha-HSD1
  5. Dihydrodiol dehydrogenase 4
  6. DD4
  7. HAKRA
Enzyme 1 Gene Name AKR1C4
Enzyme 1 Protein Sequence >Aldo-keto reductase family 1 member C4 
MDPKYQRVELNDGHFMPVLGFGTYAPPEVPRNRAVEVTKLAIEAGFRHIDSAYLYNNEEQ
VGLAIRSKIADGSVKREDIFYTSKLWCTFFQPQMVQPALESSLKKLQLDYVDLYLLHFPM
ALKPGETPLPKDENGKVIFDTVDLSATWEVMEKCKDAGLAKSIGVSNFNCRQLEMILNKP
GLKYKPVCNQVECHPYLNQSKLLDFCKSKDIVLVAHSALGTQRHKLWVDPNSPVLLEDPV
LCALAKKHKRTPALIALRYQLQRGVVVLAKSYNEQRIRENIQVFEFQLTSEDMKVLDGLN
RNYRYVVMDFLMDHPDYPFSDEY
Enzyme 1 Number of Residues 323
Enzyme 1 Molecular Weight 37095
Enzyme 1 Theoretical pI 7.19
Enzyme 1 GO Classification
Function
  • catalytic activity
  • oxidoreductase activity
Process
—
Component
—
Enzyme 1 General Function Not Available
Enzyme 1 Specific Function Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha- androstan-3alpha,17beta-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
Enzyme 1 Pathways
Enzyme 1 Reactions
  • chlordecone alcohol + NADP+ = chlordecone + NADPH + H+
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 4261710 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID P17516 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name AK1C4_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >972 bp 
ATGGATCCCAAATATCAGCGTGTAGAGCTAAATGATGGTCATTTCATGCCCGTATTGGGA
TTTGGCACCTATGCACCTCCAGAGGTTCCGAGGAACAGAGCTGTAGAGGTCACCAAATTA
GCAATAGAAGCTGGCTTCCGCCATATTGATTCTGCTTATTTATACAATAATGAGGAGCAG
GTTGGACTGGCCATCCGAAGCAAGATTGCAGATGGCAGTGTGAAGAGAGAAGACATATTC
TACACTTCAAAGCTTTGGTGCACTTTCTTTCAACCACAGATGGTCCAACCAGCCTTGGAA
AGCTCACTGAAAAAACTTCAACTGGACTATGTTGACCTCTATCTTCTTCATTTCCCAATG
GCTCTCAAGCCAGGTGAGACGCCACTACCAAAAGATGAAAATGGAAAAGTAATATTCGAC
ACAGTGGATCTCTCTGCCACATGGGAGGTCATGGAGAAGTGTAAGGATGCAGGATTGGCC
AAGTCCATCGGGGTGTCAAACTTCAACTGCAGGCAGCTGGAGATGATCCTCAACAAGCCA
GGACTCAAGTACAAGCCTGTCTGCAACCAGGTAGAATGTCATCCTTACCTCAACCAGAGC
AAACTGCTGGATTTCTGCAAGTCAAAAGACATTGTTCTGGTTGCCCACAGTGCTCTGGGA
ACCCAACGACATAAACTATGGGTGGACCCAAACTCCCCAGTTCTTTTGGAGGACCCAGTT
CTTTGTGCCTTAGCAAAGAAACACAAACGAACCCCAGCCCTGATTGCCCTGCGCTACCAG
CTGCAGCGTGGGGTTGTGGTCCTGGCCAAGAGCTACAATGAGCAGCGGATCAGAGAGAAC
ATCCAGGTTTTTGAATTCCAGTTGACATCAGAGGATATGAAAGTTCTAGATGGTCTAAAC
AGAAATTATCGATATGTTGTCATGGATTTTCTTATGGACCATCCTGATTATCCATTTTCA
GATGAATATTAG
Enzyme 1 GenBank Gene ID S68287 Link Image
Enzyme 1 GeneCard ID AKR1C4 Link Image
Enzyme 1 GenAtlas ID AKR1C4 Link Image
Enzyme 1 HGNC ID HGNC:387 Link Image
Enzyme 1 Chromosome Location 10
Enzyme 1 Locus 10p15-p14
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Qin KN, New MI, Cheng KC: Molecular cloning of multiple cDNAs encoding human enzymes structurally related to 3 alpha-hydroxysteroid dehydrogenase. J Steroid Biochem Mol Biol. 1993 Dec;46(6):673-9. [PubMed Link Image]
  2. Khanna M, Qin KN, Wang RW, Cheng KC: Substrate specificity, gene structure, and tissue-specific distribution of multiple human 3 alpha-hydroxysteroid dehydrogenases. J Biol Chem. 1995 Aug 25;270(34):20162-8. [PubMed Link Image]
  3. Khanna M, Qin KN, Cheng KC: Distribution of 3 alpha-hydroxysteroid dehydrogenase in rat brain and molecular cloning of multiple cDNAs encoding structurally related proteins in humans. J Steroid Biochem Mol Biol. 1995 Jun;53(1-6):41-6. [PubMed Link Image]
  4. Kume T, Iwasa H, Shiraishi H, Yokoi T, Nagashima K, Otsuka M, Terada T, Takagi T, Hara A, Kamataki T: Characterization of a novel variant (S145C/L311V) of 3alpha-hydroxysteroid/dihydrodiol dehydrogenase in human liver. Pharmacogenetics. 1999 Dec;9(6):763-71. [PubMed Link Image]
  5. Nishizawa M, Nakajima T, Yasuda K, Kanzaki H, Sasaguri Y, Watanabe K, Ito S: Close kinship of human 20alpha-hydroxysteroid dehydrogenase gene with three aldo-keto reductase genes. Genes Cells. 2000 Feb;5(2):111-25. [PubMed Link Image]
  6. Dufort I, Labrie F, Luu-The V: Human types 1 and 3 3 alpha-hydroxysteroid dehydrogenases: differential lability and tissue distribution. J Clin Endocrinol Metab. 2001 Feb;86(2):841-6. [PubMed Link Image]
  7. Winters CJ, Molowa DT, Guzelian PS: Isolation and characterization of cloned cDNAs encoding human liver chlordecone reductase. Biochemistry. 1990 Jan 30;29(4):1080-7. [PubMed Link Image]
  8. Deyashiki Y, Ogasawara A, Nakayama T, Nakanishi M, Miyabe Y, Sato K, Hara A: Molecular cloning of two human liver 3 alpha-hydroxysteroid/dihydrodiol dehydrogenase isoenzymes that are identical with chlordecone reductase and bile-acid binder. Biochem J. 1994 Apr 15;299 ( Pt 2):545-52. [PubMed Link Image]
  9. Binstock JM, Iyer RB, Hamby CV, Fried VA, Schwartz IS, Weinstein BI, Southren AL: Human hepatic 3 alpha-hydroxysteroid dehydrogenase: possible identity with human hepatic chlordecone reductase. Biochem Biophys Res Commun. 1992 Sep 16;187(2):760-6. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available