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MedKoo Cat#: 329849 | Name: Equilenin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Equilenin is an equine estrogen found in the urine of pregnant mares. Equilenin is also a naturally fluorescent steroid, has high binding affinity for human sex steroid-binding protein (SBP). At 4 degrees C the equilibrium association constant is approximately 6 X 10(7) M-1.

Chemical Structure

Equilenin
Equilenin
CAS#517-09-9

Theoretical Analysis

MedKoo Cat#: 329849

Name: Equilenin

CAS#: 517-09-9

Chemical Formula: C18H18O2

Exact Mass: 266.1307

Molecular Weight: 266.34

Elemental Analysis: C, 81.17; H, 6.81; O, 12.01

Price and Availability

Size Price Availability Quantity
1mg USD 450.00 2 Weeks
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Related CAS #
No Data
Synonym
Equilenin; Equilenine; d-Equilenin; (+)-Equilenin; Equilenina; NSC 9901; NSC9901; NSC-9901;
IUPAC/Chemical Name
(13S,14S)-3-hydroxy-13-methyl-12,14,15,16-tetrahydro-11H-cyclopenta[a]phenanthren-17-one
InChi Key
PDRGHUMCVRDZLQ-WMZOPIPTSA-N
InChi Code
InChI=1S/C18H18O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2-5,10,16,19H,6-9H2,1H3/t16-,18-/m0/s1
SMILES Code
O=C1CC[C@@]2([H])C(C=CC3=CC(O)=CC=C43)=C4CC[C@]12C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Formulations containing equilenin conjugates have been widely used as hormone replacement therapies for post-menopausal women.

Preparing Stock Solutions

The following data is based on the product molecular weight 266.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Uchida M, Ishibashi H, Yamamoto R, Koyanagi A, Kusano T, Tominaga N, Ishibashi Y, Arizono K. Endocrine-disrupting potentials of equine estrogens equilin, equilenin, and their metabolites, in the medaka Oryzias latipes: in silico and DNA microarray studies. J Appl Toxicol. 2015 Sep;35(9):1040-8. doi: 10.1002/jat.3098. Epub 2015 Jan 22. PubMed PMID: 25611945. 2: Jinno A, Maruyama Y, Ishizuka M, Kazusaka A, Nakamura A, Fujita S. Induction of cytochrome P450-1A by the equine estrogen equilenin, a new endogenous aryl hydrocarbon receptor ligand. J Steroid Biochem Mol Biol. 2006 Jan;98(1):48-55. Epub 2005 Sep 26. PubMed PMID: 16191477. 3: Gherezghiher TB, Michalsen B, Chandrasena RE, Qin Z, Sohn J, Thatcher GR, Bolton JL. The naphthol selective estrogen receptor modulator (SERM), LY2066948, is oxidized to an o-quinone analogous to the naphthol equine estrogen, equilenin. Chem Biol Interact. 2012 Mar 5;196(1-2):1-10. doi: 10.1016/j.cbi.2012.01.004. Epub 2012 Jan 28. PubMed PMID: 22290292; PubMed Central PMCID: PMC3319273. 4: Numazawa M, Osawa Y. Equilin and equilenin biosynthesis. Stereochemistry of aromatization of 3-hydroxy-3,5,7-androstatrien-17-one by horse placenta. J Steroid Biochem. 1987 Jan;26(1):137-43. PubMed PMID: 3821102. 5: Gatti R, Franchina M, Gioia MG, Cavrini V. HPLC-fluorescence determination of equilin and equilenin in postmenopausal women's urine. Biomed Chromatogr. 2000 Apr;14(2):82-8. PubMed PMID: 10694700. 6: Jang DS, Choi G, Cha HJ, Shin S, Hong BH, Lee HJ, Lee HC, Choi KY. Contribution of a low-barrier hydrogen bond to catalysis is not significant in ketosteroid isomerase. Mol Cells. 2015 May;38(5):409-15. doi: 10.14348/molcells.2015.2266. Epub 2015 May 7. PubMed PMID: 25947291; PubMed Central PMCID: PMC4443282. 7: Davenport L, Knutson JR, Brand L. Excited-state proton transfer of equilenin and dihydroequilenin: interaction with bilayer vesicles. Biochemistry. 1986 Mar 11;25(5):1186-95. PubMed PMID: 3964666. 8: Spink DC, Zhang F, Hussain MM, Katz BH, Liu X, Hilker DR, Bolton JL. Metabolism of equilenin in MCF-7 and MDA-MB-231 human breast cancer cells. Chem Res Toxicol. 2001 May;14(5):572-81. PubMed PMID: 11368557. 9: Eames TC, Pollack RM, Steiner RF. Orientation, accessibility, and mobility of equilenin bound to the active site of steroid isomerase. Biochemistry. 1989 Jul 25;28(15):6269-75. PubMed PMID: 2675967. 10: Kraut DA, Sigala PA, Fenn TD, Herschlag D. Dissecting the paradoxical effects of hydrogen bond mutations in the ketosteroid isomerase oxyanion hole. Proc Natl Acad Sci U S A. 2010 Feb 2;107(5):1960-5. doi: 10.1073/pnas.0911168107. Epub 2010 Jan 11. PubMed PMID: 20080683; PubMed Central PMCID: PMC2836627. 11: Karnik AV, Malviya NJ, Kulkarni AM, Jadhav BL. Synthesis and in vitro antibacterial activity of novel heterocyclic derivatives of 18-nor-equilenin. Eur J Med Chem. 2006 Jul;41(7):891-5. Epub 2006 May 26. PubMed PMID: 16730395. 12: Orstan A, Lulka MF, Eide B, Petra PH, Ross JB. Steroid-binding site of human and rabbit sex steroid binding protein of plasma: fluorescence characterization with equilenin. Biochemistry. 1986 May 6;25(9):2686-92. PubMed PMID: 3718973. 13: Zhang TL, Shi MY, Di X, Gu JK. [Fragmentation pathways of five estrogens using electrospray ionization quadrupole time-of-flight mass spectrometry]. Yao Xue Xue Bao. 2014 Apr;49(4):507-12. Chinese. PubMed PMID: 24974469. 14: Embrechts J, Lemière F, Van Dongen W, Esmans EL. Equilenin-2'-deoxynucleoside adducts: analysis with nano-liquid chromatography coupled to nano-electrospray tandem mass spectrometry. J Mass Spectrom. 2001 Mar;36(3):317-28. PubMed PMID: 11312524. 15: Liu X, Zhang F, Liu H, Burdette JE, Li Y, Overk CR, Pisha E, Yao J, van Breemen RB, Swanson SM, Bolton JL. Effect of halogenated substituents on the metabolism and estrogenic effects of the equine estrogen, equilenin. Chem Res Toxicol. 2003 Jun;16(6):741-9. PubMed PMID: 12807357. 16: Ross JB, Torres P, Petra PH. Equilenin: a specific fluorescent probe for steroid-protein interactions in sex steroid-binding protein. FEBS Lett. 1982 Nov 29;149(2):240-4. PubMed PMID: 6891343. 17: Ding S, Shapiro R, Cai Y, Geacintov NE, Broyde S. Conformational properties of equilenin-DNA adducts: stereoisomer and base effects. Chem Res Toxicol. 2008 May;21(5):1064-73. doi: 10.1021/tx800010u. Epub 2008 Apr 17. PubMed PMID: 18416538; PubMed Central PMCID: PMC2597795. 18: Partanen S. Simultaneous azo-coupling method for an estrogen sulfatase in human tissues. Histochemistry. 1983;78(2):241-9. PubMed PMID: 6874424. 19: Cho HS, Ha NC, Choi G, Kim HJ, Lee D, Oh KS, Kim KS, Lee W, Choi KY, Oh BH. Crystal structure of delta(5)-3-ketosteroid isomerase from Pseudomonas testosteroni in complex with equilenin settles the correct hydrogen bonding scheme for transition state stabilization. J Biol Chem. 1999 Nov 12;274(46):32863-8. PubMed PMID: 10551849. 20: Ding S, Shapiro R, Geacintov NE, Broyde S. Equilenin-derived DNA adducts to cytosine in DNA duplexes: structures and thermodynamics. Biochemistry. 2005 Nov 8;44(44):14565-76. PubMed PMID: 16262256.