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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

Molecular Formula C18H24O3
Molecular Weight 288.3814
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

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Stock cells of the MCF-7 clone E3 in the passage range of 160 to 190 were maintained in estrogen “rich” media and then withdrawn into an estrogen “free” media 7 days prior to seeding for growth response experiments.41 The mitogenic activity of each compound was evaluated at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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 06:08:22 UTC 2023
Edited
by admin
on Sat Dec 16 06:08:22 UTC 2023
Record UNII
IL75Q4KU3Q
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Sat Dec 16 06:08:22 UTC 2023
PRIMARY
CAS
1229-24-9
Created by admin on Sat Dec 16 06:08:22 UTC 2023 , Edited by admin on Sat Dec 16 06:08:22 UTC 2023
PRIMARY
PUBCHEM
5284655
Created by admin on Sat Dec 16 06:08:22 UTC 2023 , Edited by admin on Sat Dec 16 06:08:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID5022516
Created by admin on Sat Dec 16 06:08:22 UTC 2023 , Edited by admin on Sat Dec 16 06:08:22 UTC 2023
PRIMARY
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