Didemnin B

  • CAT Number: I003457
  • CAS Number: 77327-05-0
  • PubChem Substance ID: 122651
  • Molecular Formula: C57H89N7O15
  • Molecular Weight: 1112.4
  • Purity: ≥95%
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Didemnin B(CAS 77327-05-0) is a cyclic depsipeptide with antiviral and antitumor activity.

Catalog Number I003457
CAS Number 77327-05-0
Synonyms

Didemnin B; NSC 325319; NSC-325319; NSC325319;

Molecular Formula

C57H89N7O15

Purity 95%
Overview of Clinical Research

<span style="color:#000000;"><span style="font-family:arial,helvetica,sans-serif;"><span style="font-size:12px;">Didemnin B is a DNA and protein synthesis inhibitor. The&nbsp;<span style="font-variant-ligatures: normal; orphans: 2; widows: 2;">Phase-II clinical trials for Non-Hodgkin&#39;s lymphoma started in USA (IV-infusion) in 2000.</span></span></span></span>

IUPAC Name (2S)-N-[(2R)-1-[[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-[(2S)-2-hydroxypropanoyl]-N-methylpyrrolidine-2-carboxamide
InChI InChI=1S/C57H89N7O15/c1-15-33(8)46-44(66)29-45(67)79-49(32(6)7)48(68)34(9)50(69)58-39(26-30(2)3)54(73)64-25-17-19-41(64)56(75)62(13)43(28-37-20-22-38(77-14)23-21-37)57(76)78-36(11)47(52(71)59-46)60-51(70)42(27-31(4)5)61(12)55(74)40-18-16-24-63(40)53(72)35(10)65/h20-23,30-36,39-44,46-47,49,65-66H,15-19,24-29H2,1-14H3,(H,58,69)(H,59,71)(H,60,70)/t33-,34-,35-,36+,39-,40-,41-,42+,43-,44-,46+,47-,49-/m0/s1
InChIKey KYHUYMLIVQFXRI-SJPGYWQQSA-N
SMILES CCC(C)C1C(CC(=O)OC(C(=O)C(C(=O)NC(C(=O)N2CCCC2C(=O)N(C(C(=O)OC(C(C(=O)N1)NC(=O)C(CC(C)C)N(C)C(=O)C3CCCN3C(=O)C(C)O)C)CC4=CC=C(C=C4)OC)C)CC(C)C)C)C(C)C)O
Reference

<p style="box-sizing: border-box; margin: 2px 0px; color: rgb(52, 73, 94); font-family: &quot;Source Sans Pro&quot;, sans-serif; font-size: 14px; font-variant-ligatures: normal; orphans: 2; widows: 2;">
<span style="color:#000000;"><span style="font-size:12px;"><span style="font-family:arial,helvetica,sans-serif;">1.Potts MB, McMillan EA, Rosales TI, Kim HS, Ou YH, Toombs JE, Brekken RA, Minden MD, MacMillan JB, White MA. Mode of action and pharmacogenomic biomarkers for exceptional responders to didemnin B. Nat Chem Biol. 2015 Jun;11(6):401-8. doi: 10.1038/nchembio.1797. Epub 2015 Apr 13. PubMed PMID: 25867045; PubMed Central PMCID: PMC4433765.</span></span></span></p>
<p style="box-sizing: border-box; margin: 2px 0px; color: rgb(52, 73, 94); font-family: &quot;Source Sans Pro&quot;, sans-serif; font-size: 14px; font-variant-ligatures: normal; orphans: 2; widows: 2;">
<span style="color:#000000;"><span style="font-size:12px;"><span style="font-family:arial,helvetica,sans-serif;">2. Hetherington AM, Sawyez CG, Sutherland BG, Robson DL, Arya R, Kelly K, Jacobs RL, Borradaile NM. Treatment with didemnin B, an elongation factor 1A inhibitor, improves hepatic lipotoxicity in obese mice. Physiol Rep. 2016 Sep;4(17). pii: e12963. doi: 10.14814/phy2.12963. PubMed PMID: 27613825; PubMed Central PMCID: PMC5027364.<br />
3.Xu Y, Kersten RD, Nam SJ, Lu L, Al-Suwailem AM, Zheng H, Fenical W, Dorrestein PC, Moore BS, Qian PY. Bacterial biosynthesis and maturation of the didemnin anti-cancer agents. J Am Chem Soc. 2012 May 23;134(20):8625-32. doi: 10.1021/ja301735a. Epub 2012 Apr 6. PubMed PMID: 22458477; PubMed Central PMCID: PMC3401512.</span></span></span></p>

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