Human Metabolome Database Version 3.5

Showing metabocard for Estrone sulfate (HMDB01425)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:32 -0700
HMDB ID HMDB01425
Secondary Accession Numbers None
Metabolite Identification
Common Name Estrone sulfate
Description Estrone 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C18H22O5S
Average Molecular Weight 350.429
Monoisotopic Molecular Weight 350.118794504
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 Name estrone sulfate
CAS Registry Number 481-97-0
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 Key JKKFKPJIXZFSSB-CBZIJGRNSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Sulfated 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 Parent Sulfated Steroids
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 254.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0059 g/L ALOGPS
LogP 0.29 ALOGPS
LogP 3.83 ChemAxon
LogS -4.77 ALOGPS
pKa (strongest acidic) -1.7 ChemAxon
pKa (strongest basic) -7.5 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 80.67 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 89.07 ChemAxon
Polarizability 36.74 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Intestine
  • Placenta
  • Testes
  • Kidney
  • Liver
  • Skin
  • Platelet
  • Gonads
Pathways
Name SMPDB Link KEGG Link
Androgen and Estrogen Metabolism SMP00068 map00150 Link_out
Sulfate/Sulfite Metabolism SMP00041 map00920 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.0051 +/- 0.00045 uM Adult (>18 years old) Female Normal
Blood Detected and Quantified
0.0004 uM Adult (>18 years old) Female Normal
Blood Detected and Quantified
0.0026 +/- 0.00017 uM Adult (>18 years old) Male Normal
Blood Detected and Quantified
0.0027 +/- 0.00022 uM Adult (>18 years old) Female Normal
Blood Detected and Quantified
0.00197 +/- 0.00107 uM Adult (>18 years old) Male Normal
Blood Detected and Quantified
0.0012 +/- 0.00049 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.0008 (0.00015-0.0014) umol/mmol creatinine Adult (>18 years old) Male Normal
Urine Detected and Quantified
0.0022 (0.00095-0.0035) umol/mmol creatinine Adult (>18 years old) Female Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.002 (0.0014-0.003) uM Adult (>18 years old) Male Obesity
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 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      DrugBank Metabolite ID DBMET00530 Link_out
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB021804
      KNApSAcK ID Not Available
      Chemspider ID 2272513 Link_out
      KEGG Compound ID C02538 Link_out
      BioCyc ID ESTRONE-SULFATE Link_out
      BiGG ID 40054 Link_out
      Wikipedia Link Estrone Link_out
      NuGOwiki Link HMDB01425 Link_out
      Metagene Link HMDB01425 Link_out
      METLIN ID 3556 Link_out
      PubChem Compound 3001028 Link_out
      PDB ID Not Available
      ChEBI ID 17474 Link_out
      References
      Synthesis Reference Price, Wm. H. Alkali metal estrone sulfates. (1959), US 2917522 19591215 Patent language unavailable.
      Material Safety Data Sheet (MSDS) Not Available
      General References
      1. Choi HY, Hobkirk R: Chromatofocusing of mammalian estrone sulfate sulfohydrolase activity. J Steroid Biochem. 1986 Dec;25(6):985-9. Pubmed: 3467142 Link_out
      2. 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 Link_out
      3. 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 Link_out
      4. 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 Link_out
      5. 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 Link_out
      6. 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 Link_out
      7. 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 Link_out
      8. 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 Link_out
      9. 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 Link_out
      10. 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 Link_out
      11. 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 Link_out
      12. 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 Link_out
      13. 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 Link_out
      14. 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 Link_out
      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 Link_out

      Enzymes
      Name: Arylsulfatase D
      Reactions: Not Available
      Gene Name: ARSD
      Uniprot ID: P51689 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Arylsulfatase E
      Reactions: Not Available
      Gene Name: ARSE
      Uniprot ID: P51690 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Estrogen sulfotransferase
      Reactions:
      Phosphoadenosine phosphosulfate + Estrone unknown Adenosine 3',5'-diphosphate + Estrone sulfate details
      Gene Name: SULT1E1
      Uniprot ID: P49888 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Steryl-sulfatase
      Reactions: Not Available
      Gene Name: STS
      Uniprot ID: P08842 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Serum albumin
      Reactions: Not Available
      Gene Name: ALB
      Uniprot ID: P02768 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Transporters
      Name: Solute carrier organic anion transporter family member 1C1
      Reactions: Not Available
      Gene Name: SLCO1C1
      Uniprot ID: Q9NYB5 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Solute carrier organic anion transporter family member 1B1
      Reactions: Not Available
      Gene Name: SLCO1B1
      Uniprot ID: Q9Y6L6 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Solute carrier organic anion transporter family member 4A1
      Reactions: Not Available
      Gene Name: SLCO4A1
      Uniprot ID: Q96BD0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Solute carrier family 22 member 7
      Reactions: Not Available
      Gene Name: SLC22A7
      Uniprot ID: Q9Y694 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA