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Agosterol A

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Agosterol A
Names
IUPAC name (22R)-11α,22-Dihydroxy-5α-cholest-7-ene-3β,4β,6α-triyl triacetate
Systematic IUPAC name (1R,3aR,5S,5aS,6R,7S,9aR,9bR,10R,11aR)-10-Hydroxy-1--9a,11a-dimethyl-2,3,3a,5,5a,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopentaphenanthrene-5,6,7-triyl triacetate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C33H52O8/c1-17(2)9-12-25(37)18(3)23-10-11-24-22-15-28(40-20(5)35)30-31(41-21(6)36)27(39-19(4)34)13-14-32(30,7)29(22)26(38)16-33(23,24)8/h15,17-18,23-31,37-38H,9-14,16H2,1-8H3/t18-,23+,24-,25+,26+,27-,28-,29+,30-,31-,32+,33+/m0/s1Key: SUIRSZOPEPPNGJ-JGEDILIOSA-N
  • InChI=1/C33H52O8/c1-17(2)9-12-25(37)18(3)23-10-11-24-22-15-28(40-20(5)35)30-31(41-21(6)36)27(39-19(4)34)13-14-32(30,7)29(22)26(38)16-33(23,24)8/h15,17-18,23-31,37-38H,9-14,16H2,1-8H3/t18-,23+,24-,25+,26+,27-,28-,29+,30-,31-,32+,33+/m0/s1Key: SUIRSZOPEPPNGJ-JGEDILIOBG
SMILES
  • C(1CC21(C(3C2=C(43(CC(4OC(=O)C)OC(=O)C)C)OC(=O)C)O)C)(CCC(C)C)O
Properties
Chemical formula C33H52O8
Molar mass 576.771 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Agosterol A is a bio-active sterol which may have applications in removing multi-drug resistance in various cancers. It was first isolated from marine sponge but has also been produced synthetically.

References

  1. Chen, Zhe-Sheng; Aoki, Shunji; Komatsu, Masaharu; Ueda, Kazumitsu; Sumizawa, Tomoyuki; Furukawa, Tatsuhiko; Okumura, Hiroshi; Ren, Xiao-Qin; Belinsky, Martin G.; Lee, Kun; Kruh, Gary D.; Kobayashi, Motomasa; Akiyama, Shin-ichi (2001). "Reversal of drug resistance mediated by multidrug resistance protein (MRP) 1 by dual effects of agosterol a on MRP1 function". International Journal of Cancer. 93 (1): 107–113. doi:10.1002/ijc.1290. ISSN 0020-7136. PMID 11391629.
  2. Aoki, Shunji; Chen, Zhe-Sheng; Higasiyama, Kimihiko; Setiawan, I; Akiyama, Shin-ichi; Kobayashi, Motomasa (2001). "Reversing Effect of Agosterol A, a Spongean Sterol Acetate, on Multidrug Resistance in Human Carcinoma Cells". Japanese Journal of Cancer Research. 92 (8): 886–895. doi:10.1111/j.1349-7006.2001.tb01177.x. ISSN 0910-5050. PMC 5926837. PMID 11509122.
  3. Murakami, Nobutoshi; Sugimoto, Masanori; Morita, Mari; Kobayashi, Motomasa (2001). "Total Synthesis of Agosterol A: an MDR-Modulator from a Marine Sponge". Chemistry: A European Journal. 7 (12): 2663–2670. doi:10.1002/1521-3765(20010618)7:12<2663::AID-CHEM26630>3.0.CO;2-U. ISSN 0947-6539. PMID 11465457.


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