IUPAC/Chemical Name
(S)-N-((4S,6S,7R,9R)-4-amino-7-(3-aminopropanoyl)-6-formyl-9-hydroxy-2,11-dimethyl-5,8-dioxo-7-phenyldodecan-6-yl)-2-hydroxy-N,4-dimethylpent-4-enamide
InChi Key
ZPYMSTAWPQJBRU-IEMGZYBISA-N
InChi Code
InChI=1S/C31H47N3O7/c1-19(2)15-23(33)27(39)30(18-35,34(7)29(41)25(37)17-21(5)6)31(26(38)13-14-32,22-11-9-8-10-12-22)28(40)24(36)16-20(3)4/h8-12,18-20,23-25,36-37H,5,13-17,32-33H2,1-4,6-7H3/t23-,24+,25-,30-,31+/m0/s1
SMILES Code
CN(C([C@@H](O)CC(C)=C)=O)[C@]([C@@](C([C@H](O)CC(C)C)=O)(C(CCN)=O)c1ccccc1)(C([C@H](CC(C)C)N)=O)C=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
573.73
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: Hamano K, Kinoshita M, Furuya K, Miyamoto M, Takamatsu Y, Hemmi A, Tanzawa K. Leualacin, a novel calcium blocker from Hapsidospora irregularis. I. Taxonomy, fermentation, isolation, physico-chemical and biological properties. J Antibiot (Tokyo). 1992 Jun;45(6):899-905. Erratum in: J Antibiot (Tokyo) 1992 Aug;45(8):C-4. PubMed PMID: 1500357.
2: Hu MK, Yang FC, Chou CC, Yen MH. Synthesis and evaluation of backbone/amide-modified analogs of leualacin. Bioorg Med Chem Lett. 1999 Feb 22;9(4):563-8. PubMed PMID: 10098664.
3: Hamano K, Kinoshita M, Tanzawa K, Yoda K, Ohki Y, Nakamura T, Kinoshita T. Leualacin, a novel calcium blocker from Hapsidospora irregularis. II. Structure determination. J Antibiot (Tokyo). 1992 Jun;45(6):906-13. Erratum in: J Antibiot (Tokyo) 1992 Aug;45(8):C-4. PubMed PMID: 1500358.
4: Zhang S, Qiu Y, Kakule TB, Lu Z, Xu F, Lamb JG, Reilly CA, Zheng Y, Sham SW, Wang W, Xuan L, Schmidt EW, Zhan J. Identification of Cyclic Depsipeptides and Their Dedicated Synthetase from Hapsidospora irregularis. J Nat Prod. 2017 Feb 24;80(2):363-370. doi: 10.1021/acs.jnatprod.6b00808. Epub 2017 Jan 20. PubMed PMID: 28106998; PubMed Central PMCID: PMC5975237.
5: McLaren KL. Total Synthesis of the Cyclic Depsipeptide Leualacin. J Org Chem. 1996 Apr 19;61(8):2914. PubMed PMID: 11667139.