Synonym
Isariin; Isariin D; Isariin B; Isariin C; NSC 135015; NSC-135015; NSC135015;
IUPAC/Chemical Name
(3S,6S,9R,12S,19R)-9-isobutyl-3,12-diisopropyl-6-methyl-19-nonyl-1-oxa-4,7,10,13,16-pentaazacyclononadecane-2,5,8,11,14,17-hexaone
InChi Key
KIJLRIARMCGDJZ-YSWCBTLJSA-N
InChi Code
InChI=1S/C33H59N5O7/c1-9-10-11-12-13-14-15-16-24-18-26(39)34-19-27(40)37-28(21(4)5)32(43)36-25(17-20(2)3)31(42)35-23(8)30(41)38-29(22(6)7)33(44)45-24/h20-25,28-29H,9-19H2,1-8H3,(H,34,39)(H,35,42)(H,36,43)(H,37,40)(H,38,41)/t23-,24+,25+,28-,29-/m0/s1
SMILES Code
CC(C)[C@@H](C(N[C@@H](C(N[C@@H](C)C(N[C@@H](C(C)C)C(O1)=O)=O)=O)CC(C)C)=O)NC(CNC(C[C@H]1CCCCCCCCC)=O)=O
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
>3 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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
637.86
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.
| 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: Sabareesh V, Ranganayaki RS, Raghothama S, Bopanna MP, Balaram H, Srinivasan MC, Balaram P. Identification and characterization of a library of microheterogeneous cyclohexadepsipeptides from the fungus Isaria. J Nat Prod. 2007 May;70(5):715-29. Epub 2007 May 4. PubMed PMID: 17477570.
2: Baute R, Deffieux G, Merlet D, Baute MA, Neveu A. New insecticidal cyclodepsipeptides from the fungus Isaria felina. I. Production, isolation and insecticidal properties of isariins B, C and D. J Antibiot (Tokyo). 1981 Oct;34(10):1261-5. PubMed PMID: 7198111.
3: Langenfeld A, Blond A, Gueye S, Herson P, Nay B, Dupont J, Prado S. Insecticidal cyclodepsipeptides from Beauveria felina. J Nat Prod. 2011 Apr 25;74(4):825-30. doi: 10.1021/np100890n. Epub 2011 Mar 25. PubMed PMID: 21438588.
4: Okada K, Kurosawa Y, Hiramoto M. Solid phase synthesis of isariin, a long chain beta-hydroxy acid-containing cyclodepsipeptide, and its diastereoisomer. Chem Pharm Bull (Tokyo). 1974 Sep;22(9):2136-41. PubMed PMID: 4452208.
5: Du FY, Li XM, Zhang P, Li CS, Wang BG. Cyclodepsipeptides and other O-containing heterocyclic metabolites from Beauveria felina EN-135, a marine-derived entomopathogenic fungus. Mar Drugs. 2014 May 13;12(5):2816-26. doi: 10.3390/md12052816. PubMed PMID: 24828289; PubMed Central PMCID: PMC4052318.
6: Deffieux G, Merlet D, Baute R, Bourgeois G, Baute MA, Neveu A. New insecticidal cyclodepsipeptides from the fungus Isaria felina. II. Structure elucidation of isariins B, C and D. J Antibiot (Tokyo). 1981 Oct;34(10):1266-70. PubMed PMID: 7198112.
