| Common Name |
16b-Hydroxyestradiol
| Description |
16b-Hydroxyestradiol is a hydroxylated metabolite of estradiol or estrone that has a hydroxyl group at C3-beta, 16-alpha, and 17-beta position. Estriol is a major urinary estrogen. During pregnancy, large amount of estriol is produced by the placenta. Isomers with inversion of the hydroxyl group or groups are called epiestriol.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
16-EpiestriolChEBI
16beta,17beta-EstriolChEBI
16beta-Hydroxy-17beta-estradiolChEBI
ActriolChEBI
EpiestriolChEBI
EpiestriolumChEBI
EpioestriolumChEBI
Estra-1,3,5(10)-triene-3,16beta,17-triolChEBI
Estra-1,3,5(10)-triene-3,16beta,17beta-triolChEBI
16b,17b-EstriolGenerator
16β,17β-estriolGenerator
16b-Hydroxy-17b-estradiolGenerator
16β-hydroxy-17β-estradiolGenerator
Estra-1,3,5(10)-triene-3,16b,17-triolGenerator
Estra-1,3,5(10)-triene-3,16β,17-triolGenerator
Estra-1,3,5(10)-triene-3,16b,17b-triolGenerator
Estra-1,3,5(10)-triene-3,16β,17β-triolGenerator
16-Epi-estriolHMDB
16-EpiestratriolHMDB
(16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triolMeSH
(16beta,17beta)-Estra-1,3,5(10)-triene-3,16,17-triolMeSH
16 alpha Hydroxy estradiolMeSH
16-alpha-Hydroxy-estradiolMeSH
16alpha,17beta EstriolMeSH
16alpha,17beta-EstriolMeSH
16beta Hydroxy estradiolMeSH
16beta-Hydroxy-estradiolMeSH
EstriolMeSH
OvestinMeSH
| Chemical Formlia |
C18H24O3
| Average Molecliar Weight |
288.3814
| Monoisotopic Molecliar Weight |
288.172544634
| IUPAC Name |
(1S,10R,11S,13S,14R,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,13,14-triol
| Traditional Name |
(1S,10R,11S,13S,14R,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,13,14-triol
| CAS Registry Number |
547-81-9
| SMILES |
[H][C@@]12C[C@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
| InChI Identifier |
InChI=1S/C18H24O3/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/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17+,18+/m1/s1
| InChI Key |
PROQIPRRNZUXQM-ZMSHIADSSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Detected but not 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
| 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 Solubility0.12 mg/mLALOGPS
logP2.54ALOGPS
logP2.67ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.27 m3·mol-1ChemAxon
Polarizability32.91 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0290000000-c1aaa2c05e9fd0323ef6View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-2900000000-3b5302633684d0176de2View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-7900000000-1705b9f7f2b39ae9ba41View in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot Available
Normal
details
UrineDetected but not Quantified Not AvailableNot AvailableNormal
21543078
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| 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 |
FDB021970
| KNApSAcK ID |
Not Available
| Chemspider ID |
62155
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00347
| Metagene Link |
HMDB00347
| METLIN ID |
5336
| PubChem Compound |
68929
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Shogaol
References |
| Synthesis Reference |
Ling, Yangzhi; Xu, Chunfang; Fang, Guofu; Liu, Weiqin. Improved synthesis of estriol via hydroboration. Yiyao Gongye (1988), 19(12), 533-5. |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
- Xu X, Veenstra TD, Fox SD, Roman JM, Issaq HJ, Falk R, Saavedra JE, Keefer LK, Ziegler RG: Measuring fifteen endogenous estrogens simultaneously in human urine by high-performance liquid chromatography-mass spectrometry. Anal Chem. 2005 Oct 15;77(20):6646-54. [PubMed:16223252 ]
- Nambara T, Matsuki Y, Igarashi J, Kawarada Y, Kurata M: Studies on steroid conjugates. XII. Occurrence of 16-epiestriol 16-glucuronide in human pregnancy urine. Chem Pharm Bull (Tokyo). 1974 Oct;22(10):2242-5. [PubMed:4377544 ]
- Adlercreutz H, Martin F, Pulkkinen M, Dencker H, Rimer U, Sjoberg NO, Tikkanen MJ: Intestinal metabolism of estrogens. J Clin Endocrinol Metab. 1976 Sep;43(3):497-505. [PubMed:956337 ]
|
PMID: 11470258