Estrin (compound)

Estrin

Names
IUPAC name

Estra-1,3,5(10)-triene

Systematic IUPAC name

(3aS,3bS,9bS,11aS)-11a-Methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene

Other names

Estratriene

Identifiers

CAS Number

* 1217-09-0

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL1627934

ChemSpider |

* 133001

PubChem CID

* 150899

UNII |

* F274X7VR4M Y

InChI

* InChI=1S/C18H24/c1-18-11-4-7-17(18)16-9-8-13-5-2-3-6-14(13)15(16)10-12-18/h2-3,5-6,15-17H,4,7-12H2,1H3/t15-,16-,17+,18+/m1/s1

Key: HLCRYAZDZCJZFG-BDXSIMOUSA-N

SMILES

* C[C@@]12CCC[C@H]1[C@@H]3CCC4=CC=CC=C4[C@H]3CC2

Properties

Chemical formula

| C18H24
Molar mass | 240.39 g/mol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Estrin (American English), or oestrin (British English), also known as estra-1,3,5(10)-triene, is an estrane steroid. It is dehydrogenated estrane with double bonds specifically at the C1, C3, and C5(10) positions. Estrin is a parent structure of the estrogen steroid hormones estradiol, estrone, and estriol, which have also been known as dihydroxyestrin, ketohydroxyestrin, and trihydroxyestrin, respectively.[1][2]

Unlike its estrogen derivatives, estrin itself possesses minimal estrogenic activity, as hydroxyl and/or keto substitutions at the C3 and C17 positions are critical for high binding affinity to the estrogen receptors.[3][4] Estrin has been found to be on the order of 1,000-fold less potent than estradiol in inducing estrogenic responses in vitro.[5][6][3] In addition to estrin, estratrien-17β-ol, which lacks the 3-hydroxyl group of estradiol, and 3-hydroxyestratriene, which lacks the 17β-hydroxyl group of estradiol, both have measurable affinity for the estrogen receptor and are able to activate the receptor and induce progesterone receptor expression.[6][7][3]

The term estrin is also a synonym for estrogen.[8] It was coined by Sir Alan S. Parkes and C. W. Bellerby in 1926 to describe the hormone secreted from the ovaries that induces estrus in animals (i.e., estrogen).[8]

v * d * e Structures of major endogenous estrogens

Estrone (E1)

Estradiol (E2)

Estriol (E3)

Estetrol (E4)

Note the hydroxyl (–OH) groups: estrone (E1) has one, estradiol (E2) has two, estriol (E3) has three, and estetrol (E4) has four.

## See also

* 1-Keto-1,2,3,4-tetrahydrophenanthrene

## References

1. ↑ Biskind, Morton S. (1935). "Commercial glandular products". Journal of the American Medical Association 105 (9): 667. doi:10.1001/jama.1935.92760350007009a. ISSN 0002-9955.
2. ↑ "Estrogenic Hormones: Their Clinical Usage". Cal West Med 49 (5): 362–6. 1938. PMID 18744783.
3. ↑ 3.0 3.1 3.2 "The estradiol pharmacophore: ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site". Steroids 62 (3): 268–303. 1997. doi:10.1016/s0039-128x(96)00242-5. PMID 9071738.
4. ↑ Thomas L. Lemke; David A. Williams (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1395–. ISBN 978-1-60913-345-0. https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA1395.
5. ↑ "Regulation of prolactin synthesis in vitro by estrogenic and antiestrogenic derivatives of estradiol and estrone". Endocrinology 124 (4): 1717–26. April 1989. doi:10.1210/endo-124-4-1717. PMID 2924721.
6. ↑ 6.0 6.1 Moudgil VK, ed (1987). "Estrogen structure-receptor function relationships". Recent Advances in Steroid Hormone Action. Walter de Gruyter. pp. 443–466.
7. ↑ "Ligand-mediated modulation of estrogen receptor conformation by estradiol analogs". Biochemistry 32 (38): 10109–15. September 1993. doi:10.1021/bi00089a029. PMID 8399136.
8. ↑ 8.0 8.1 Marc A. Fritz; Leon Speroff (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 750–. ISBN 978-1-4511-4847-3. https://books.google.com/books?id=KZLubBxJEwEC&pg=PA750.

* v
* t
* e

Steroid classification

C17|

* Gonane

C18|

* Estrane: Dehydrogenated: Estrene
* Estradiene
* Estratriene; Substituted: Estratrienolone
* Estratrienediol
* Estratrienetriol

C19|

* Androstane: Dehydrogenated: Androstene
* Androstadiene
* Androstatriene; Substituted: Androstanol
* Androstenol
* Androstanone
* Androstenone
* Androstanediol
* Androstenediol
* Androstanedione
* Androstenedione
* Androstenetrione
* Androstanolone
* Androstenolone
* Androstadienol
* Androstadienone; Etiocholane

C20|

* 19-Norpregnane

C21|

* Pregnane: Dehydrogenated: Pregnene
* Pregnadiene
* Pregnatriene; Substituted: Pregnanediol
* Pregnanetriol
* Pregnenediol
* Pregnanedione
* Pregnenedione
* 5α-Pregnane
* 5β-Pregnane

C23|

* Cardanolide

C24|

* Cholane
* Bile acid

C27|

* Cholestane

Functional group|

* 17-Ketosteroid
* Hydroxysteroid
* Halogenated steroid

Elements removed|

* Norsteroid
* Secosteroid

Elements replaced|

* Azasteroid

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