| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:07:58 -0700 |
| HMDB ID |
HMDB00145 |
| Secondary Accession Numbers |
|
| Metabolite Identification |
| Common Name |
Estrone |
| Description |
Estrone is a major mammalian estrogen. The conversion of the natural C19 steroids, testosterone and androstenedione into estrone is dependent on a complex key reaction catalyzed by the cytochrome P450 aromatase (EC 1.14.14.1, unspecific monooxygenase), which is expressed in many tissues of the adult human (e.g. ovary, fat tissue), but not in the liver. The ovaries after menopause continue to produce androstenedione and testosterone in significant amounts and these androgens are converted in fat, muscle, and skin into estrone. When women between the ages of 45 and 64 years have prophylactic oophorectomy (when hysterectomy is performed for benign disease to prevent the development of ovarian cancer), evidence suggests that oophorectomy increases the subsequent risk of coronary heart disease (CHD) and osteoporosis. Whereas 14,000 women die of ovarian cancer every year nearly 490,000 women die of heart disease and 48,000 women die within 1 year after hip fracture. Therefore, the decision to perform prophylactic oophorectomy should be approached with great caution for the majority of women who are at low risk of developing ovarian cancer. Steroid sulfatase (EC 3.1.6.2, STS) hydrolyzes steroid sulfates, such as estrone sulfate to estrone which can be converted to steroids with potent estrogenic properties, that is, estradiol; STS activity is much higher in breast tumors and high levels of STS mRNA expression in tumors are associated with a poor prognosis. The biological roles of estrogens in tumorigenesis are certainly different between the endometrium and breast, although both are considered "estrogen-dependent tissues". 17beta-hydroxysteroid dehydrogenases (EC 1.1.1.62, 17-HSDs) are enzymes involved in the formation of active sex steroids. estrone is interconverted by two enzymes 17-HSD types. Type 1 converts estrone to estradiol and Type 2 catalyzes the reverse reaction. (PMID: 17653961 , 17513923 , 17470679 , 17464097 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- (+)-Estrone
- 1,3,5(10)-Estratrien-3-ol-17-one
- 3-Hydroxy-17-keto-estra-1,3,5-triene
- 3-Hydroxyestra-1,3,5(10)-trien-17-one
- 3-Hydroxyestra-1,3,5(10)-triene-17-one
- 3-Hydroxyoestra-1,3,5(10)-trien-17-one
- D1,3,5(10)-Estratrien-3-ol-17-one
|
| Chemical Formula |
C18H22O2 |
| Average Molecular Weight |
270.3661 |
| Monoisotopic Molecular Weight |
270.161979948 |
| IUPAC Name |
(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-14-one |
| Traditional IUPAC Name |
estrone |
| CAS Registry Number |
53-16-7 |
| SMILES |
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 |
| InChI Identifier |
InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1 |
| InChI Key |
DNXHEGUUPJUMQT-CBZIJGRNSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Steroids and Steroid Derivatives |
| Sub Class |
Estrogens and Derivatives |
| Other Descriptors |
- 17-oxo steroid(ChEBI)
- Aromatic Homomonocyclic Compounds
- Aromatic Homopolycyclic Compounds
- C18 steroids (estrogens) and derivatives(KEGG)
- C18 steroids (estrogens) and derivatives(Lipidmaps)
- Estrane and derivatives(KEGG)
- Estrane(KEGG)
- Estrogens(KEGG)
- Hydroxysteroids
- Ketosteroids
- estrogen(ChEBI)
|
| Substituents |
- Cyclohexane
- Cyclohexene
- Ketone
- Phenanthrene
- Phenol
- Phenol Derivative
- Sesquiterpene Backbone
- Tetralin
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| Direct Parent |
Estrogens and Derivatives |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
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| Biofunction |
- Cell signaling
- Component of Androgen and estrogen metabolism
- Component of Sulfur metabolism
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
- Endoplasmic reticulum
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| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
258 - 260 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
0.03 mg/mL |
Not Available |
| LogP |
3.13 |
HANSCH,C ET AL. (1995) |
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| Predicted Properties |
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| Spectra |
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| Biological Properties |
| Cellular Locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
- Endoplasmic reticulum
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| Biofluid Locations |
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| Tissue Location |
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| Pathways |
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| Normal Concentrations |
|
| Blood |
Detected and Quantified |
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0.00017 +/- 0.000071 uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.00020 (0.00011-0.00030) uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.00012 (0.0-0.00024) uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Urine |
Detected and Quantified |
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0.0013 +/- 0.00085 umol/mmol creatinine |
Adult (>18 years old) |
Female |
Normal |
Not Available |
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| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.00022 (0.00013-0.00038) uM |
Adult (>18 years old) |
Male |
Positive coronary arteriograms |
Not Available |
| Blood |
Detected and Quantified |
|
0.00021 (0.00011-0.00037) uM |
Adult (>18 years old) |
Both |
Minor electrocardiongraphic abnormalities and/or arrhythmia with negative coronary arteriograms |
Not Available |
| Blood |
Detected and Quantified |
|
0.00035 (0.00014-0.00056) uM |
Adult (>18 years old) |
Female |
Menstrual cycle (follicular phase) |
Not Available |
| Blood |
Detected and Quantified |
|
0.00050 (0.00028-0.00074) uM |
Adult (>18 years old) |
Female |
Menstrual cycle (midcycle) |
Not Available |
| Blood |
Detected and Quantified |
|
0.00030 (0.00018-0.00042) uM |
Adult (>18 years old) |
Female |
Menstrual cycle (luteal phase) |
Not Available |
|
| Associated Disorders and Diseases |
| Disease References |
| Menstrual cycle |
- The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.
|
| Normal |
- The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.
|
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| Associated OMIM IDs |
None |
| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB012798 |
| KNApSAcK ID |
C00003663  |
| Chemspider ID |
5660  |
| KEGG Compound ID |
C00468  |
| BioCyc ID |
ESTRONE  |
| BiGG ID |
35059  |
| Wikipedia Link |
Estrone  |
| NuGOwiki Link |
HMDB00145  |
| Metagene Link |
HMDB00145  |
| METLIN ID |
264  |
| PubChem Compound |
5870  |
| PDB ID |
J3Z  |
| ChEBI ID |
17263  |
| References |
| Synthesis Reference |
Kocovsky, Paved; Baines, Richard S. Synthesis of estrone via a thallium(III)-mediated fragmentation of a 19-hydroxyandrost-5-ene precursor. Tetrahedron Letters (1993), 34(38), 6139-40. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Czernik PJ, Little JM, Barone GW, Raufman JP, Radominska-Pandya A: Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa. Drug Metab Dispos. 2000 Oct;28(10):1210-6.
Pubmed: 10997942
- Pfeiffer E, Graf E, Gerstner S, Metzler M: Stimulation of estradiol glucuronidation: a protective mechanism against estradiol-mediated carcinogenesis? Mol Nutr Food Res. 2006 Apr;50(4-5):385-9.
Pubmed: 16598814
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| Enzymes |
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| Name: |
Estrogen sulfotransferase
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| Reactions: |
- 3'-phosphoadenylyl sulfate + estrone = adenosine 3',5'-bisphosphate + estrone 3-sulfate [RN:R02350]
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| Gene Name: |
SULT1E1 |
| Uniprot ID: |
P49888  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Steryl-sulfatase
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| Reactions: |
- 3beta-hydroxyandrost-5-en-17-one 3-sulfate + H2O = 3beta-hydroxyandrost-5-en-17-one + sulfate [RN:R03404]
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| Gene Name: |
STS |
| Uniprot ID: |
P08842  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
3-keto-steroid reductase
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| Reactions: |
- 4alpha-methyl-5alpha-cholest-7-en-3beta-ol + NADP+ = 4alpha-methyl-5alpha-cholest-7-en-3-one + NADPH + H+ [RN:R05691]
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| Gene Name: |
HSD17B7 |
| Uniprot ID: |
P56937  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 3A4
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| Reactions: |
- (1) taurochenodeoxycholate + NADPH + H+ + O2 = taurohyocholate + NADP+ + H2O [RN:R07205]
- (2) lithocholate + NADPH + H+ + O2 = hyodeoxycholate + NADP+ + H2O [RN:R07206]
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| Gene Name: |
CYP3A4 |
| Uniprot ID: |
P08684  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 2C9
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| Reactions: |
- (R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
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| Gene Name: |
CYP2C9 |
| Uniprot ID: |
P11712  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 2C19
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| Reactions: |
- (R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
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| Gene Name: |
CYP2C19 |
| Uniprot ID: |
P33261  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 3A43
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP3A43 |
| Uniprot ID: |
Q9HB55  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 1B1
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP1B1 |
| Uniprot ID: |
Q16678  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 2C18
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP2C18 |
| Uniprot ID: |
P33260  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 2F1
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP2F1 |
| Uniprot ID: |
P24903  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 4X1
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP4X1 |
| Uniprot ID: |
Q8N118  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 2B6
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP2B6 |
| Uniprot ID: |
P20813  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 3A5
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP3A5 |
| Uniprot ID: |
P20815  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 1A1
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP1A1 |
| Uniprot ID: |
P04798  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 2A13
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP2A13 |
| Uniprot ID: |
Q16696  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 3A7
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP3A7 |
| Uniprot ID: |
P24462  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 4B1
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP4B1 |
| Uniprot ID: |
P13584  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 4Z1
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP4Z1 |
| Uniprot ID: |
Q86W10  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 1A2
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP1A2 |
| Uniprot ID: |
P05177  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 19A1
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP19A1 |
| Uniprot ID: |
P11511  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 2C8
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP2C8 |
| Uniprot ID: |
P10632  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 2S1
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP2S1 |
| Uniprot ID: |
Q96SQ9  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 2J2
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP2J2 |
| Uniprot ID: |
P51589  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 2A7
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP2A7 |
| Uniprot ID: |
P20853  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 2A6
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP2A6 |
| Uniprot ID: |
P11509  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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