Synonym
Scopafungin; N-29479; U 29479; U-29,479; Scopafungin malonate; Amycin A
IUPAC/Chemical Name
Propanedioic acid, mono(5,7,9,19,23,25,27,31,33,34,35-undecahydroxy-15-(11-((imino(methylamino)methyl)amino)-1,3-dimethyl-7-undecenyl)-8,14,18,22,26,30-hexamethyl-17-oxo-16,37-dioxabicyclo(31.3.1)heptatriaconta-10,12,20-trien-3-yl) ester malonate
InChi Key
HIBYARUCWIEDPI-OZHDXRHSSA-N
InChi Code
InChI=1S/C59H103N3O18.C3H4O4/c1-34(18-14-12-10-11-13-17-25-62-58(60)61-9)26-38(5)55-37(4)19-15-16-20-45(64)39(6)49(68)28-42(63)27-43(78-54(74)32-53(72)73)29-44-30-51(70)56(75)59(77,80-44)33-52(71)36(3)22-23-46(65)40(7)50(69)31-48(67)35(2)21-24-47(66)41(8)57(76)79-55;4-2(5)1-3(6)7/h10-11,15-16,19-21,24,34-52,55-56,63-71,75,77H,12-14,17-18,22-23,25-33H2,1-9H3,(H,72,73)(H3,60,61,62);1H2,(H,4,5)(H,6,7)/b11-10+,19-15-,20-16+,24-21+;
SMILES Code
O=C(OC(CC(O)CC(O)C(C)C(O)/C=C/C=C\C(C)C(C(C)CC(C)CCC/C=C/CCCNC(NC)=N)O1)CC(O2)CC(O)C(O)C2(O)CC(O)C(C)CCC(O)C(C)C(O)CC(O)C(C)/C=C/C(O)C(C)C1=O)CC(O)=O.O=C(O)CC(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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
1,246.54
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: Johnson LE, Dietz A. Scopafungin, a crystalline antibiotic produced by Streptomyces hygroscopicus var. enhygrus var. nova. Appl Microbiol. 1971 Sep;22(3):303-8. PubMed PMID: 4940870; PubMed Central PMCID: PMC376304.
2: Bergy ME, Hoeksema H. Scopafungin, a crystalline endomycin component. J Antibiot (Tokyo). 1972 Jan;25(1):39-43. PubMed PMID: 5010644.
3: Takesako K, Nakamura T, Obayashi A, Iwasaki S, Namikoshi M, Okuda S, Beppu T. Demalonyl derivatives of azalomycin F4 and scopafungin. J Antibiot (Tokyo). 1986 May;39(5):713-6. PubMed PMID: 3733520.
4: Reusser F. Scopafungin, an inhibitor of oxidative phosphorylation in mitochondria. Biochem Pharmacol. 1972 Apr 1;21(7):1031-8. PubMed PMID: 4339110.
5: Mogi T, Matsushita K, Murase Y, Kawahara K, Miyoshi H, Ui H, Shiomi K, Omura S, Kita K. Identification of new inhibitors for alternative NADH dehydrogenase (NDH-II). FEMS Microbiol Lett. 2009 Feb;291(2):157-61. doi: 10.1111/j.1574-6968.2008.01451.x. Epub 2008 Dec 5. PubMed PMID: 19076229.
6: Stefanelli S, Corti E, Montanini N, Denaro M, Sarubbi E. Inhibitors of type-I interleukin-1 receptor from microbial metabolites. J Antibiot (Tokyo). 1997 Jun;50(6):484-9. PubMed PMID: 9268004.
7: Kumazawa S, Asami Y, Awane K, Ohtani H, Fukuchi C, Mikawa T, Hayase T. Structural studies of new macrolide antibiotics, shurimycins A and B. J Antibiot (Tokyo). 1994 Jun;47(6):688-96. PubMed PMID: 8040074.
8: Dolak LA, Reusser F, Baczynskyj L, Mizsak SA, Hannon BR, Castle TM. Desertomycin: purification and physical-chemical properties. J Antibiot (Tokyo). 1983 Jan;36(1):13-9. PubMed PMID: 6678910.
9: Kuimova TF, Kazakov GA, Inshakova TA. [Spontaneous crystallization of antibiotic substance during submerged fermentation of Actinomyces hygroscopicus]. Mikrobiologiia. 1976 JUL-AUG;45(4):746-9. Russian. PubMed PMID: 979694.
