Synonym
WS 9326A; WS-326A; WS9326A;
IUPAC/Chemical Name
(E)-N-((3S,6R,9R,12R,15R,21S,22R)-6-(2-amino-2-oxoethyl)-12-benzyl-18-((Z)-4-hydroxybenzylidene)-9-((R)-1-hydroxyethyl)-3-(hydroxymethyl)-15-isobutyl-19,22-dimethyl-2,5,8,11,14,17,20-heptaoxo-1-oxa-4,7,10,13,16,19-hexaazacyclodocosan-21-yl)-3-(2-((E)-pent-1-en-1-yl)phenyl)acrylamide
InChi Key
BVVWVQZZLUNSNV-PNRTYFKVSA-N
InChi Code
InChI=1S/C54H68N8O13/c1-7-8-10-17-36-18-13-14-19-37(36)22-25-45(67)60-47-33(5)75-54(74)42(30-63)59-49(69)41(29-44(55)66)58-52(72)46(32(4)64)61-50(70)40(27-34-15-11-9-12-16-34)56-48(68)39(26-31(2)3)57-51(71)43(62(6)53(47)73)28-35-20-23-38(65)24-21-35/h9-25,28,31-33,39-42,46-47,63-65H,7-8,26-27,29-30H2,1-6H3,(H2,55,66)(H,56,68)(H,57,71)(H,58,72)(H,59,69)(H,60,67)(H,61,70)/b17-10+,25-22+,43-28-/t32-,33-,39-,40-,41-,42+,46-,47+/m1/s1
SMILES Code
OC[C@@H](C(O[C@H](C)[C@H](NC(/C=C/c1ccccc1/C=C/CCC)=O)C(N(C)/C(C(N[C@H](CC(C)C)C(N2)=O)=O)=C\c3ccc(O)cc3)=O)=O)NC([C@@H](CC(N)=O)NC([C@@H]([C@H](O)C)NC([C@H]2Cc4ccccc4)=O)=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
1,037.18
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: Desouky SE, Shojima A, Singh RP, Matsufuji T, Igarashi Y, Suzuki T, Yamagaki T, Okubo K, Ohtani K, Sonomoto K, Nakayama J. Cyclodepsipeptides produced by actinomycetes inhibit cyclic-peptide-mediated quorum sensing in Gram-positive bacteria. FEMS Microbiol Lett. 2015 Jul;362(14). pii: fnv109. doi: 10.1093/femsle/fnv109. Epub 2015 Jul 5. PubMed PMID: 26149266.
2: Yu Z, Vodanovic-Jankovic S, Kron M, Shen B. New WS9326A congeners from Streptomyces sp. 9078 inhibiting Brugia malayi asparaginyl-tRNA synthetase. Org Lett. 2012 Sep 21;14(18):4946-9. Epub 2012 Sep 12. PubMed PMID: 22967068; PubMed Central PMCID: PMC3460372.
3: Hayashi K, Hashimoto M, Shigematsu N, Nishikawa M, Ezaki M, Yamashita M, Kiyoto S, Okuhara M, Kohsaka M, Imanaka H. WS9326A, a novel tachykinin antagonist isolated from Streptomyces violaceusniger no. 9326. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities. J Antibiot (Tokyo). 1992 Jul;45(7):1055-63. PubMed PMID: 1381343.
4: Shigematsu N, Kayakiri N, Okada S, Tanaka H. Total synthesis of WS9326A, a potent tachykinin antagonist from Streptomyces violaceoniger. Chem Pharm Bull (Tokyo). 1997 Feb;45(2):236-42. PubMed PMID: 9118439.
5: Hashimoto M, Hayashi K, Murai M, Fujii T, Nishikawa M, Kiyoto S, Okuhara M, Kohsaka M, Imanaka H. WS9326A, a novel tachykinin antagonist isolated from Streptomyces violaceusniger no. 9326. II. Biological and pharmacological properties of WS9326A and tetrahydro-WS9326A (FK224). J Antibiot (Tokyo). 1992 Jul;45(7):1064-70. Erratum in: J Antibiot (Tokyo) 1992 Dec;45(12):C-9. PubMed PMID: 1381344.
