| Common Name |
16a-Hydroxyestrone
| Description |
Estrone (also oestrone) is an estrogenic hormone secreted by the ovary. Its molecliar formlia is C18H22O2. estrone has a melting point of 254.5 degrees Celsius. estrone is one of the three estrogens, which also include estriol and estradiol. estrone is the least prevalent of the three hormones, estradiol being prevalent almost always in a female body, estriol being prevalent primarily during pregnancy. estrone slifate is relevant to health and disease due to its conversion to estrone slifate, a long-lived derivative of estrone. estrone slifate acts as a pool of estrone which can be converted as needed to the more active estradiol.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
16 alpha OHEChEBI
3,16alpha-Dihydroxy-1,3,5(10)-estratrien-17-oneChEBI
3,16alpha-Dihydroxyestra-1,3,5(10)-trien-17-oneChEBI
Estra-1,3,5(10)-triene-3,16alpha-diol-17-oneChEBI
16 a OHEGenerator
16 α oheGenerator
3,16a-Dihydroxy-1,3,5(10)-estratrien-17-oneGenerator
3,16α-dihydroxy-1,3,5(10)-estratrien-17-oneGenerator
3,16a-Dihydroxyestra-1,3,5(10)-trien-17-oneGenerator
3,16α-dihydroxyestra-1,3,5(10)-trien-17-oneGenerator
Estra-1,3,5(10)-triene-3,16a-diol-17-oneGenerator
Estra-1,3,5(10)-triene-3,16α-diol-17-oneGenerator
16 alpha-HydroxyestroneHMDB
3,16a-Dihydroxy-estra-1,3,5(10)-trien-17-oneHMDB
16 beta-HydroxyestroneMeSH
16-alpha-HydroxyestroneMeSH
16-HydroxyestroneMeSH
| Chemical Formlia |
C18H22O3
| Average Molecliar Weight |
286.3655
| Monoisotopic Molecliar Weight |
286.15689457
| IUPAC Name |
(1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one
| Traditional Name |
16α-hydroxyestrone
| CAS Registry Number |
566-76-7
| SMILES |
[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
| InChI Identifier |
InChI=1S/C18H22O3/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/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1
| InChI Key |
WPOCIZJTELRQMF-QFXBJFAPSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
Food
| Biofunction |
Cell signaling
Fuel and energy storage
Fuel or energy source
Hormones, Membrane component
Membrane integrity/stability
| Application |
Nutrients
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Extracellliar
Membrane (predicted from logP)
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.047 mg/mLALOGPS
logP2.45ALOGPS
logP3.44ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity80.57 m3·mol-1ChemAxon
Polarizability32.06 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| GC-MS |
GC-MS Spectrum – GC-MS (1 MEOX; 2 TMS)splash10-0019-3941100000-3a930f8cc95b733c8653View in MoNA
| GC-MS |
GC-MS Spectrum – GC-MS (1 MEOX; 2 TMS)splash10-0019-3941100000-3e52ec60bd9142c09b74View in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane (predicted from logP)
| Biofluid Locations |
Blood
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified0.00078 (0.00076-0.00081) uMAdlit (>18 years old)FemaleNormal
14569192
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified0.000817 (0.0008-0.00084) uMAdlit (>18 years old)FemaleBreast cancer
14569192
details
| Associated Disorders and Diseases |
| Disease References |
| Perillyl alcohol administration for cancer treatment |
- Caliey JA, Zmuda JM, Danielson ME, Ljung BM, Bauer DC, Cummings SR, Kliler LH: Estrogen metabolites and the risk of breast cancer in older women. Epidemiology. 2003 Nov;14(6):740-4. [PubMed:14569192 ]
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB021959
| KNApSAcK ID |
Not Available
| Chemspider ID |
103012
| KEGG Compound ID |
C05300
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00335
| Metagene Link |
HMDB00335
| METLIN ID |
2580
| PubChem Compound |
115116
| PDB ID |
J2Z
| ChEBI ID |
776
Product: Dabigatran (ethyl ester hydrochloride)
References |
| Synthesis Reference |
Knuppen, R.; Breuer, H. Biogenesis of 11b-hydroxyestrone and 16a-hydroxyestrone by adrenal tissue. Biochimica et Biophysica Acta (1962), 58 147-8. |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
Not Available |
Enzymes
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Capable of catalyzing the interconversion of testosterone and androstenedione, as well as estradiol and estrone. Also has 20-alpha-HSD activity. Uses NADH while EDH17B3 uses NADPH.
- Gene Name:
- HSD17B2
- Uniprot ID:
- P37059
- Molecular weight:
- 42784.75
- General function:
- Involved in oxidoreductase activity
- Specific function:
- NAD-dependent 17-beta-hydroxysteroid dehydrogenase with highest activity towards estradiol. Has very low activity towards testosterone. The heteroteramer with CBR4 has NADH-dependent 3-ketoacyl-acyl carrier protein reductase activity. May play a role in biosynthesis of fatty acids in mitochondria.
- Gene Name:
- HSD17B8
- Uniprot ID:
- Q92506
- Molecular weight:
- 26973.56
- General function:
- Involved in estradiol 17-beta-dehydrogenase activity
- Specific function:
- Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH.
- Gene Name:
- HSD17B1
- Uniprot ID:
- P14061
- Molecular weight:
- 34949.715
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Responsible for the reduction of the keto group on the C-3 of sterols.
- Gene Name:
- HSD17B7
- Uniprot ID:
- P56937
- Molecular weight:
- 38205.77
PMID: 7851497