Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:32 UTC
HMDB IDHMDB01425
Secondary Accession NumbersNone
Metabolite Identification
Common NameEstrone sulfate
DescriptionEstrone sulfate is a sulfated estrone derivative. Estrone sulfate acts as a long-lived reservoir that can be converted as needed to the more active estradiol (from estrone via 17 beta-hydroxysteroid dehydrogenase). Estrone Sulfate (E1S) is the most abundant circulating estrogen in non-pregnant women as well as normal men. Estrone is primarily synthesized from estrone sulfate. Estrone is an estrogenic hormone secreted by the ovaries and adipose tissues. Estrone is one of the three estrogens found in humans. The other two are estriol and estradiol. Estrone is the least prevalent of the three. Estradiol plays a critical role on reproductive and sexual functioning in women and it also affects other organs including the bones. Estriol is an estrogen that is prevalent primarily during pregnancy.
Structure
Thumb
Synonyms
  1. Conestoral
  2. Estrogenic substances
  3. Estrone
  4. Estrone hydrogen sulfate
  5. Estrone hydrogen sulphate
  6. Estrone 3-sulfate
  7. Estrone 3-sulphate
  8. Estrone sulfate
  9. Estrone sulfate sodium
  10. Estrone sulphate
  11. Estrone sulphate sodium
  12. Estrone-3-sulfate
  13. Estrone-3-sulphate
  14. Premarin
  15. Sodium estrone 3-monosulfate
  16. Sodium estrone 3-monosulphate
  17. Sodium estrone 3-sulfate
  18. Sodium estrone 3-sulphate
Chemical FormulaC18H22O5S
Average Molecular Weight350.429
Monoisotopic Molecular Weight350.118794504
IUPAC Name[(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-5-yl]oxidanesulfonic acid
Traditional IUPAC Nameestrone sulfate
CAS Registry Number481-97-0
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=CC=C(OS(O)(=O)=O)C=C3CC[C@@]21[H]
InChI Identifier
InChI=1S/C18H22O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,18+/m1/s1
InChI KeyJKKFKPJIXZFSSB-CBZIJGRNSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassSulfated Steroids
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • C18 steroids (estrogens) and derivatives(KEGG)
  • C18 steroids (estrogens) and derivatives(Lipidmaps)
  • Estrogens(KEGG)
  • Sulfates(KEGG)
  • steroid sulfate(ChEBI)
Substituents
  • 17 Keto Steroid
  • Cyclohexane
  • Cyclohexene
  • Estrogen Skeleton
  • Ketone
  • Organic Sulfuric Acid Monoester
  • Phenanthrene
  • Sesquiterpene Backbone
  • Sulfate Ester
  • Tetralin
Direct ParentSulfated Steroids
Ontology
StatusDetected and Quantified
Origin
  • Drug or steroid metabolite
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Androgen and estrogen metabolism
  • Component of Sulfur metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Waste products
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point254.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.0059 g/LALOGPS
logP0.29ALOGPS
logP3.83ChemAxon
logS-4.8ALOGPS
pKa (strongest acidic)-1.7ChemAxon
pKa (strongest basic)-7.5ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count1ChemAxon
polar surface area80.67ChemAxon
rotatable bond count2ChemAxon
refractivity89.07ChemAxon
polarizability36.74ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Gonads
  • Intestine
  • Kidney
  • Liver
  • Placenta
  • Platelet
  • Skin
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Androgen and Estrogen MetabolismSMP00068map00150
Sulfate/Sulfite MetabolismSMP00041map00920
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.0051 +/- 0.00045 uMAdult (>18 years old)FemaleNormal
BloodDetected and Quantified0.0004 uMAdult (>18 years old)FemaleNormal
BloodDetected and Quantified0.0026 +/- 0.00017 uMAdult (>18 years old)MaleNormal
BloodDetected and Quantified0.0027 +/- 0.00022 uMAdult (>18 years old)FemaleNormal
BloodDetected and Quantified0.00197 +/- 0.00107 uMAdult (>18 years old)MaleNormal
BloodDetected and Quantified0.0012 +/- 0.00049 uMAdult (>18 years old)BothNormal
UrineDetected and Quantified0.0008 (0.00015-0.0014) umol/mmol creatinineAdult (>18 years old)MaleNormal
UrineDetected and Quantified0.0022 (0.00095-0.0035) umol/mmol creatinineAdult (>18 years old)FemaleNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.002 (0.0014-0.003) uMAdult (>18 years old)MaleObesity
Associated Disorders and Diseases
Disease References
Obesity
  • Brind J, Strain G, Miller L, Zumoff B, Vogelman J, Orentreich N: Obese men have elevated plasma levels of estrone sulfate. Int J Obes. 1990 Jun;14(6):483-6. Pubmed: 2401584
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00530
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021804
KNApSAcK IDNot Available
Chemspider ID2272513
KEGG Compound IDC02538
BioCyc IDESTRONE-SULFATE
BiGG ID40054
Wikipedia LinkEstrone
NuGOwiki LinkHMDB01425
Metagene LinkHMDB01425
METLIN ID3556
PubChem Compound3001028
PDB IDNot Available
ChEBI ID17474
References
Synthesis ReferencePrice, Wm. H. Alkali metal estrone sulfates. (1959), US 2917522 19591215 Patent language unavailable.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Matsushima S, Maeda K, Kondo C, Hirano M, Sasaki M, Suzuki H, Sugiyama Y: Identification of the hepatic efflux transporters of organic anions using double-transfected Madin-Darby canine kidney II cells expressing human organic anion-transporting polypeptide 1B1 (OATP1B1)/multidrug resistance-associated protein 2, OATP1B1/multidrug resistance 1, and OATP1B1/breast cancer resistance protein. J Pharmacol Exp Ther. 2005 Sep;314(3):1059-67. Epub 2005 May 18. Pubmed: 15901800
  2. Satoh H, Yamashita F, Tsujimoto M, Murakami H, Koyabu N, Ohtani H, Sawada Y: Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B. Drug Metab Dispos. 2005 Apr;33(4):518-23. Epub 2005 Jan 7. Pubmed: 15640378
  3. Craddock AL, Love MW, Daniel RW, Kirby LC, Walters HC, Wong MH, Dawson PA: Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter. Am J Physiol. 1998 Jan;274(1 Pt 1):G157-69. Pubmed: 9458785
  4. Choi HY, Hobkirk R: Chromatofocusing of mammalian estrone sulfate sulfohydrolase activity. J Steroid Biochem. 1986 Dec;25(6):985-9. Pubmed: 3467142
  5. Sherstha R, McKinley C, Russ P, Scherzinger A, Bronner T, Showalter R, Everson GT: Postmenopausal estrogen therapy selectively stimulates hepatic enlargement in women with autosomal dominant polycystic kidney disease. Hepatology. 1997 Nov;26(5):1282-6. Pubmed: 9362373
  6. Gniot-Szulzycka J, Jakubowska A: Oestrone sulphate sulphohydrolase activity in nuclear envelopes from human placenta cell nuclei. Acta Biochim Pol. 1991;38(1):7-16. Pubmed: 1796709
  7. Fredricsson B, Carlstrom K, Kjessler B, Lindstedt J, Ploen L, Ritzen M, de la Torre B: Incomplete androgen insensitivity: asymmetry in morphology and steroid profile and metabolism of the gonads. An analysis of a case. Acta Endocrinol (Copenh). 1985 Dec;110(4):564-71. Pubmed: 4090916
  8. Fuchikami H, Satoh H, Tsujimoto M, Ohdo S, Ohtani H, Sawada Y: Effects of herbal extracts on the function of human organic anion-transporting polypeptide OATP-B. Drug Metab Dispos. 2006 Apr;34(4):577-82. Epub 2006 Jan 13. Pubmed: 16415120
  9. Milewich L, Sontheimer RD, Herndon JH Jr: Steroid sulfatase activity in epidermis of acne-prone and non-acne-prone skin of patients with acne vulgaris. Arch Dermatol. 1990 Oct;126(10):1312-4. Pubmed: 2145810
  10. Stewart JD, Lou Y, Squires EJ, Coussens PM: Using human microarrays to identify differentially expressed genes associated with increased steroidogenesis in boars. Anim Biotechnol. 2005;16(2):139-51. Pubmed: 16335808
  11. Ekaratanawong S, Anzai N, Jutabha P, Miyazaki H, Noshiro R, Takeda M, Kanai Y, Sophasan S, Endou H: Human organic anion transporter 4 is a renal apical organic anion/dicarboxylate exchanger in the proximal tubules. J Pharmacol Sci. 2004 Mar;94(3):297-304. Pubmed: 15037815
  12. Creidi P, Faivre B, Agache P, Richard E, Haudiquet V, Sauvanet JP: Effect of a conjugated oestrogen (Premarin) cream on ageing facial skin. A comparative study with a placebo cream. Maturitas. 1994 Oct;19(3):211-23. Pubmed: 7799828
  13. Bomba-Opon DA, Niesluchowska-Frydrych B, Szucka-May H, Kaminski P, Marianowski L: [Effects of oral administration of estrogen replacement therapy in surgical menopause] Ginekol Pol. 2001 Dec;72(12A):1377-82. Pubmed: 11883282
  14. AvRuskin TW, Krishnan N, Juan CS: Congenital adrenal hypoplasia and male pseudohermaphroditism due to DAX1 mutation, SF1 mutation or neither: a patient report. J Pediatr Endocrinol Metab. 2004 Aug;17(8):1125-32. Pubmed: 15379426
  15. Michaud DS, Manson JE, Spiegelman D, Barbieri RL, Sepkovic DW, Bradlow HL, Hankinson SE: Reproducibility of plasma and urinary sex hormone levels in premenopausal women over a one-year period. Cancer Epidemiol Biomarkers Prev. 1999 Dec;8(12):1059-64. Pubmed: 10613337

Enzymes

Gene Name:
ARSD
Uniprot ID:
P51689
Gene Name:
ARSE
Uniprot ID:
P51690
Gene Name:
SULT1E1
Uniprot ID:
P49888
Reactions
Phosphoadenosine phosphosulfate + Estrone unknown Adenosine 3',5'-diphosphate + Estrone sulfatedetails
Gene Name:
STS
Uniprot ID:
P08842
Gene Name:
ALB
Uniprot ID:
P02768

Transporters

Gene Name:
SLC22A7
Uniprot ID:
Q9Y694