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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H24O3
Molecular Weight 288.3814
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 6.ALPHA.-HYDROXYESTRADIOL

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]3([H])C4=C(C=C(O)C=C4)[C@@H](O)C[C@@]23[H]

InChI

InChIKey=QZZRQURPSRWTLG-WOVZSMEKSA-N
InChI=1S/C18H24O3/c1-18-7-6-12-11-3-2-10(19)8-14(11)16(20)9-13(12)15(18)4-5-17(18)21/h2-3,8,12-13,15-17,19-21H,4-7,9H2,1H3/t12-,13-,15+,16+,17+,18+/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9365180 | https://www.ncbi.nlm.nih.gov/pubmed/18982491 | https://www.ncbi.nlm.nih.gov/pubmed/24098659 | https://www.ncbi.nlm.nih.gov/pubmed/9357533 | https://www.ncbi.nlm.nih.gov/pubmed/2395886

6α-Hydroxyestradiol is one of major metabolites of endogenous estrogens, as well as a positional isomer of estriol. Transformation of estradiol to 6α-Hydroxyestradiol is a major metabolic pathway of estradiol in the liver. CYP1A2 and CYP3A4 are the major enzymes catalyzing the 6α-Hydroxyestradiol of estradiol.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Human breast cancer cell line MCF-7 was used for activity evaluation. Stock cells of the MCF-7 clone E3 in the passage range of 160 to 190 were maintained in estrogen “rich” media and then withdrawn into an estrogen “free” media 7 days prior to seeding for growth response experiments.41 The mitogenic activity of each compound was evaluated at concentrations of 10^-12, 10^-11, 10^-10, 10^-9, 10^-8, 10^-7, and 10^-6 M. All cell growth determinations included positive controls treated with 10^-11 M E2 as well as negative controls devoid of estrogen treatment. In addition, a check of estrogen contamination of culture conditions for each experiment was made by including cells treated only with 10^-7 M ICI. Treatments with this “pure” antiestrogen served to validate the negative control flasks since only experiments with negative control cell counts within 10% of ICI treated flasks at the end of the treatment period (indicating no significant estrogen contamination) were considered valid assays of each compound’s mitogenic potential.
Name Type Language
6.ALPHA.-HYDROXYESTRADIOL
Common Name English
ESTRA-1,3,5(10)-TRIENE-3,6.ALPHA.,17.BETA.-TRIOL
Systematic Name English
E-2540
Code English
E 2540
Common Name English
ESTRA-1,3,5(10)-TRIENE-3,6,17-TRIOL, (6.ALPHA.,17.BETA.)-
Systematic Name English
6.ALPHA.-HYDROXY-17.BETA.-ESTRADIOL
Common Name English
1,3,5-ESTRATRIENE-3,6.ALPHA.,17.BETA.-TRIOL
Common Name English
Code System Code Type Description
FDA UNII
IL75Q4KU3Q
Created by admin on Sat Dec 16 06:08:22 GMT 2023 , Edited by admin on Sat Dec 16 06:08:22 GMT 2023
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CAS
1229-24-9
Created by admin on Sat Dec 16 06:08:22 GMT 2023 , Edited by admin on Sat Dec 16 06:08:22 GMT 2023
PRIMARY
PUBCHEM
5284655
Created by admin on Sat Dec 16 06:08:22 GMT 2023 , Edited by admin on Sat Dec 16 06:08:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID5022516
Created by admin on Sat Dec 16 06:08:22 GMT 2023 , Edited by admin on Sat Dec 16 06:08:22 GMT 2023
PRIMARY