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AB142519

2-Hydroxyestradiol, Cytochrome P450 metabolite of estradiol

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MW 288.4 Da. Cytochrome P450 metabolite of estradiol with low affinity for estrogen receptors. Stimulates increase in β-adrenergic receptor density. Biological effects mediated by 2-methoxyestradiol after methylation of 2OHE by catechol-O-methyltransferase (COMT). Active in vivo and in vitro.

View Alternative Names

Atherosclerosis, susceptibility to, included, DKFZp686N23123, ER, ER-alpha, ER-beta, ER[a], ER[b], ESR, ESR B, ESR BETA, ESR1_HUMAN, ESR2_HUMAN, ESRA, ESTR B, Era, Erb, Erb2, Estr, Estra, Estradiol Receptor alpha, Estradiol Receptor beta, Estradiol receptor, Estrogen Receptor 1, Estrogen Receptor 2, Estrogen receptor, Estrogen receptor 1 (alpha), Estrogen receptor 2 (ER beta), Estrogen receptor 2 ER beta, Estrogen receptor alpha, Estrogen receptor beta, Estrogen receptor beta 4, Estrogen resistance, included, HDL cholesterol, augmented response of, to hormone replacement, included, Myocardial infarction, susceptibility to, included, NR3A1, NR3A2, Nuclear receptor subfamily 3 group A member 1, Nuclear receptor subfamily 3 group A member 2, OTTHUMP00000017718, OTTHUMP00000017719, RNESTROR, estrogen nuclear receptor beta variant a, estrogen nuclear receptor beta variant b

1 Images
Chemical Structure - 2-Hydroxyestradiol, Cytochrome P450 metabolite of estradiol (AB142519)
  • Chemical Structure

Lab

Chemical Structure - 2-Hydroxyestradiol, Cytochrome P450 metabolite of estradiol (AB142519)

2D chemical structure image of ab142519, 2-Hydroxyestradiol, Cytochrome P450 metabolite of estradiol

Key facts

CAS number

362-05-0

Form

Solid

form

Molecular weight

288.4 Da

Molecular formula

C<sub>1</sub><sub>8</sub>H<sub>2</sub><sub>4</sub>O<sub>3</sub>

PubChem

247304

Nature

Synthetic

Solubility

Soluble in ethanol to about 20 mg/ml

Soluble in DMSO to about 20 mg/ml

Soluble in DMF to about 20 mg/ml

Biochemical name

2-Hydroxyestradiol

Biological description

Cytochrome P450 metabolite of estradiol with low affinity for estrogen receptors. Stimulates increase in β-adrenergic receptor density. Biological effects mediated by 2-methoxyestradiol after methylation of 2OHE by catechol-O-methyltransferase (COMT). Active in vivo and in vitro.

Canonical smiles

CC12CCC3C(C1CCC2O)CCC4=CC(=C(C=C34)O)O

Isomeric smiles

C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=C(C=C34)O)O

InChi

InChI=1S/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1

InChiKey

DILDHNKDVHLEQB-XSSYPUMDSA-N

IUPAC Name

(8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-2,3,17-triol

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Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
The product can be stored for up to 12 months
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Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

The Estrogen Receptor beta (ERβ) also known as NR3A2 acts mechanically by serving as a nuclear hormone receptor. We can find ERβ in different tissues including ovary prostate lungs and brain. This receptor has a mass around 59 kDa. ERβ binds to steroid hormones such as estradiol influencing the transcription of various genes. Hormone binding causes conformational changes facilitating the recruitment of co-regulators to target genes allowing it to regulate downstream biological processes.
Biological function summary

ERβ influences development reproduction and cell differentiation. It may function as part of a receptor complex interacting with other members of the nuclear receptor family to modulate transcription of target genes. The receptor plays a role in modulating cell proliferation and apoptosis. Its presence in various tissues suggests it has a broad function potentially affecting both normal development and pathology much like its counterpart Estrogen Receptor alpha.

Pathways

ERβ plays significant roles in the endocrine signaling and cell signaling pathways. It works within these systems to mediate responses to estradiol and similar compounds such as 2-hydroxyestradiol and coumestrol. It interacts notably with the MAPK signaling pathway contributing to transcriptional regulation and cellular responses. ERα another estrogen receptor often accompanies ERβ as both receptors mediate the biological effects of estrogens sharing several signaling partners and target genes.

ERβ associates with breast cancer and osteoporosis. Its reduced expression or altered function links to various pathological conditions suggesting it has protective roles against these diseases. In breast cancer ERβ potentially influences disease progression with connections to proteins like HER2. In osteoporosis ERβ helps modulate the balance of bone resorption and formation working alongside proteins like cytochrome p450 which contributes to estrogen metabolism.
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Product protocols

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