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Human Metabolome Database Version 2.5

 

Showing metabocard for 17a-Estradiol (HMDB00429)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:58
Accession Number HMDB00429
Secondary Accession Numbers Not Available
Common Name 17a-Estradiol
Description 17a-estradiol is found in the estrogen patch. The estrogen patch is a delivery system for estradiol used as hormone replacement therapy to treat the symptoms of menopause, such as hot flashes and vaginal dryness, and to prevent osteoporosis. Originally marketed as Vivelle (Novartis), it was discontinued in 2003 and reintroduced in a smaller form as Vivelle-Dot. Although the estrogen is given transdermally rather than in the standard oral tablets, the estrogen patch carries similar risks and benefits as more conventional forms of estrogen-only hormone replacement therapy.
Synonyms
  1. 1,3,5-Estratriene-3,17a-diol
  2. 13b-Methyl-1,3,5(10)-gonatriene-3,17a-diol
  3. 17-Epiestradiol
  4. 17a-Oestradiol
  5. 3,17-Dihydroxyestratriene
  6. 3,17a-Dihydroxyestra-1,3,5(10)-triene
  7. 3,17a-Dihydroxyoestra-1,3,5(10)-triene
  8. Alfatradiol
  9. Epiestradiol
  10. Epiestrol
  11. Estra-1,3,5(10)-triene-3,17a-diol
  12. Oestra-1,3,5(10)-triene-3,17a-diol
  13. a-Estradiol
  14. alpha-Estradiol
Chemical IUPAC Name (8S,9S,13S,14S,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta
Chemical Formula C18H24O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Dihydroxy steroids
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • phenol or hydroxyhetarene
  • aromatic compound
Biofunction
  • Hormones, Membrane component
Application
—
Source
  • Endogenous
Average Molecular Weight 272.382
Monoisotopic Molecular Weight 272.177643
Isomeric SMILES C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(O)=C4)[C@@H]1CC[C@H]2O
Canonical SMILES CC12CCC3C(CCC4=C3C=CC(O)=C4)C1CCC2O
KEGG Compound ID C02537 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00429 Link Image
Metagene Link HMDB00429 Link Image
METLIN ID 5418 Link Image
PubChem Compound 68570 Link Image
PubChem Substance 8143675 Link Image
ChEBI ID Not Available
CAS Registry Number 57-91-0
InChI Identifier InChI=1/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1
Synthesis Reference Gardi, Rinaldo; Pedrali, Cesare; Ercoli, Alberto. 3-Cyclopentyl ethers of 16,17-oxygenated estrogens. New synthesis of 17a-estradiol. Gazzetta Chimica Italiana (1963), 93(8-9), 1028-43.
Melting Point (Experimental) 216-219 oC
Experimental Water Solubility 0.0039 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 0.021300001 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 3.57 [Predicted by ALOGPS]; 4.2 [Predicted by PubChem via XLOGP]; 3.94 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
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
Show Peaklist
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)
Biofluid Location
  • Blood
  • Urine
Tissue Location Not Available
Concentrations (Normal)
Biofluid Blood
Value 0.3200 +/- 0.0001 uM
Age Adult:>18 yrs old
Sex Male
Patient information Normal
Comments Not Available
References
  • Cheng CY, Boettcher B: The effect of steroids on the in vitro migration of washed human spermatozoa in modified Tyrode's solution or in fasting human blood serum. Fertil Steril. 1979 Nov;32(5):566-70. [PubMed Link Image]
Biofluid Urine
Value 0.00262+/-0.00065 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Female
Patient information Normal
Comments Not Available
References
  • Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35. [PubMed Link Image]
Biofluid Urine
Value 2.3 +/- 1.6 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Pitt J, Carpenter K, Wilcken B, Boneh A: 3-Hydroxyglutarate excretion is increased in ketotic patients: implications for glutaryl-CoA dehydrogenase deficiency testing. J Inherit Metab Dis. 2002 May;25(2):83-8. [PubMed Link Image]
Concentrations (Abnormal)
Biofluid Urine
Value 9.4 +/- 5.0 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Condition Glutaryl-CoA dehydrogenase deficiency (GDHD)
Comments Not Available
References
  • Pitt J, Carpenter K, Wilcken B, Boneh A: 3-Hydroxyglutarate excretion is increased in ketotic patients: implications for glutaryl-CoA dehydrogenase deficiency testing. J Inherit Metab Dis. 2002 May;25(2):83-8. [PubMed Link Image]
Associated Disorders
Condition References
Glutaryl-CoA dehydrogenase deficiency (GDHD)
  • Pitt J, Carpenter K, Wilcken B, Boneh A: 3-Hydroxyglutarate excretion is increased in ketotic patients: implications for glutaryl-CoA dehydrogenase deficiency testing. J Inherit Metab Dis. 2002 May;25(2):83-8. [PubMed Link Image]
OMIM ID Not Available
Pathways Not Available
General References Not Available