Synonym
Calpinactam; FKI-4905; FKI 4905; FKI4905;
IUPAC/Chemical Name
(R)-4-((S)-2-((S)-2-((R)-2-amino-3-phenylpropanamido)-4-methylpentanamido)-3-(1H-imidazol-5-yl)propanamido)-5-(((2R,3S)-3-methyl-1-oxo-1-(((S)-2-oxoazepan-3-yl)amino)pentan-2-yl)amino)-5-oxopentanoic acid
InChi Key
GPDRWULXOJRYOR-XHGFRBTRSA-N
InChi Code
InChI=1S/C38H57N9O8/c1-5-23(4)32(38(55)44-27-13-9-10-16-41-34(27)51)47-35(52)28(14-15-31(48)49)43-37(54)30(19-25-20-40-21-42-25)46-36(53)29(17-22(2)3)45-33(50)26(39)18-24-11-7-6-8-12-24/h6-8,11-12,20-23,26-30,32H,5,9-10,13-19,39H2,1-4H3,(H,40,42)(H,41,51)(H,43,54)(H,44,55)(H,45,50)(H,46,53)(H,47,52)(H,48,49)/t23-,26+,27-,28+,29-,30-,32+/m0/s1
SMILES Code
N[C@@H](C(N[C@H](C(N[C@@H](CC1=CN=CN1)C(N[C@H](CCC(O)=O)C(N[C@@]([C@@H](C)CC)([H])C(N[C@@H]2C(NCCCC2)=O)=O)=O)=O)=O)CC(C)C)=O)CC3=CC=CC=C3
Purity
>95% (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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
767.93
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: Koyama N, Kojima S, Nonaka K, Masuma R, Matsumoto M, Omura S, Tomoda H. Calpinactam, a new anti-mycobacterial agent, produced by Mortierella alpina FKI-4905. J Antibiot (Tokyo). 2010 Apr;63(4):183-6. doi: 10.1038/ja.2010.14. Epub 2010 Feb 26. PMID: 20186169.
2: Nagai K, Koyama N, Sato N, Yanagisawa C, Tomoda H. Synthesis and antimycobacterial activity of calpinactam derivatives. Bioorg Med Chem Lett. 2012 Dec 15;22(24):7739-41. doi: 10.1016/j.bmcl.2012.09.069. Epub 2012 Oct 12. PMID: 23116887.
3: Koyama N, Kojima S, Fukuda T, Nagamitsu T, Yasuhara T, Omura S, Tomoda H. Structure and total synthesis of fungal calpinactam, a new antimycobacterial agent. Org Lett. 2010 Feb 5;12(3):432-5. doi: 10.1021/ol902553z. PMID: 20030344.
4: Nakahara H, Sennari G, Noguchi Y, Hirose T, Sunazuka T. Development of a nitrogen-bound hydrophobic auxiliary: application to solid/hydrophobic-tag relay synthesis of calpinactam. Chem Sci. 2023 May 1;14(25):6882-6889. doi: 10.1039/d3sc01432k. PMID: 37389244; PMCID: PMC10306108.
5: Kirchgaessner L, Wurlitzer JM, Seibold PS, Rakhmanov M, Gressler M. A genetic tool to express long fungal biosynthetic genes. Fungal Biol Biotechnol. 2023 Feb 1;10(1):4. doi: 10.1186/s40694-023-00152-3. PMID: 36726159; PMCID: PMC9893682.
6: Yagi A, Uchida R, Hamamoto H, Sekimizu K, Kimura KI, Tomoda H. Anti- Mycobacterium activity of microbial peptides in a silkworm infection model with Mycobacterium smegmatis. J Antibiot (Tokyo). 2017 May;70(5):685-690. doi: 10.1038/ja.2017.23. PMID: 28446822.
