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Bovine Metabolome Database



Showing metabocard for Estriol (BMDB00153)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-07-28 16:28:10
Accession Number BMDB00153
Common Name Estriol
Description Estriol is a metabolite of estrone metabolized via 16alpha-hydroxyestrone through the enzyme 16alpha-hydroxysteroid dehydrogenase (EC 1.1.1.147) or to 2- or 4-hydroxyestrone (catechol estrogens) by the action of catecho-O-methyltransferase (EC 2.1.1.6). The latter metabolites can be formed in the brain and may compete with receptors for catecholamines. Metabolites are conjugated with sulfate or glucuronide before excretion by the kidney. During pregnancy, estriol constitutes 60-70% of the total estrogens, increasing to 300-500-fold in relation to non-pregnant women. The late term human fetus produces relatively large amounts of 16 alphahydroxy DHEA, which serves the mother as a precursor of estriol. It has been shown that 90% of the precursors for the formation of estriol are of fetal origin. If abnormal maternal serum screening results, specifically low levels of unconjugated estriol in the second trimester are detected, a diagnosis of Smith-Lemli-Opitz syndrome (SLOS),or RSH is suspected. SLOS is an autosomal recessive disorder caused by mutations of the gene encoding 7-dehydrocholesterol reductase (EC 1.3.1.21, DHCR7). (PMID: 16202579, 16112271, 16097001)
Synonyms
  1. 13b-Methyl-1,3,5(10)-gonatriene-3,16a,17b-triol
  2. 16-alpha,17-beta-Estriol
  3. 16-alpha,17-beta-Oestriol
  4. 16-alpha-Hydroxyestradiol
  5. 16a,17b-Estriol
  6. 16a-Estriol
  7. 16a-Hydroxyestradiol
  8. 16alpha,17beta-Estriol
  9. 16alpha,17beta-Oestriol
  10. 16alpha-Hydroxy-17beta-estradiol
  11. 16alpha-Hydroxyestradiol
  12. 16alpha-Hydroxyoestradiol
  13. 3,16a,17b-Estriol
  14. 3,16a,17b-Trihydroxyestra-1,3,5(10)-triene
  15. 3,16alpha,17beta-Trihydroxy-1,3,5(10)-estratriene
  16. 3,16alpha,17beta-Trihydroxyestra-1,3,5(10)-triene
  17. Aacifemine
  18. Colpogyn
  19. Colpovister
  20. Destriol
  21. Deuslon A
  22. Deuslon-A
  23. Estra-1,3,5(10)-triene-3,16a,17b-triol
  24. Estratriol
  25. Estriel
  26. Estriol
  27. Follicular hormone hydrate
  28. Gynasan
  29. Hemostyptanon
  30. Holin V
  31. Hormomed
  32. Incurin
  33. Klimax E
  34. Klimoral
  35. Oekolp
  36. Oestratriol
  37. Oestriol
  38. Oestriolum
  39. Orestin
  40. Orgastyptin
  41. Ortho-Gynest
  42. Ovesterin
  43. Ovestin
  44. Ovestinon
  45. Ovestrion
  46. Ovo-Vinces
  47. Theelol
  48. Tridestrin
  49. Trihydroxyestrin
  50. Triovex
Chemical IUPAC Name (8S,9S,13S,14S,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol
Chemical Formula C18H24O3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Ketosteroids
Family
  • Mammalian_Metabolite
Species
  • secondary alcohol; 1,2-diol; phenol or hydroxyhetarene; aromatic compound
Biofunction
  • Hormones, Membrane component
Application
Source
  • Endogenous
Average Molecular Weight 288.381
Monoisotopic Molecular Weight 288.172546
Isomeric SMILES C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(O)=C4)[C@@H]1C[C@@H](O)[C@@H]2O
Canonical SMILES CC12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(O)C2O
KEGG Compound ID C05141 Link Image
BioCyc ID Not Available
BiGG ID 45207 Link Image
Wikipedia Link Estriol Link Image
METLIN ID 2581 Link Image
PubChem Compound 5756 Link Image
PubChem Substance 7887358 Link Image
ChEBI ID 27974 Link Image
CAS Registry Number 50-27-1
InChI Identifier InChI=1/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1
Synthesis Reference Leeds, Norma S.; Fukushima, David K.; Gallagher, T. F. Studies of steroid ring D epoxides of enol acetates; a new synthesis of estriol and of androstane-3b,16a,17b-triol. Journal of the American Chemical Society (1954), 76 2943-8.
Melting Point (Experimental) 282 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.441 mg/mL [MEYLAN,WM et al. (1996)]; 0.119 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity 2.45 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity 2.54 [Predicted by ALOGPS]; 3.6 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID 1X8V Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Bruker)
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
Download File
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High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
  • Cytoplasm
  • endoplasmic reticulum
Biofluid Location
  • Breast_Milk
Tissue Location
Tissue References
Adrenal Cortex
Adrenal Gland
Placenta
Testes
Concentrations (Normal)
Biofluid Breast_Milk
Value 3.121E-05 +/- 6.935E-06 uM
Age N/A
Sex N/A
Condition Normal
Comments Commercial whole milk.
References
Biofluid Breast_Milk
Value 2.843E-05 +/- 1.0000E-05 uM
Age N/A
Sex N/A
Condition Normal
Comments commercial skim milk.
References
Concentrations (Abnormal) Not Available
Pathway Names
  • Androgen and Estrogen Metabolism
HMDB Pathways
Name Androgen and Estrogen Metabolism
Image Show Link Image
KEGG Pathways
Name Androgen and Estrogen Metabolism
Image Show Link Image
SimCell Pathways
Name Androgen and Estrogen Metabolism
Image Show Link Image
Graph
SBML
General References
  1. Wikipedia Link Image