Synonym
OM173-αA, Nanaomycin αA, Nanaomycin A methyl ester
IUPAC/Chemical Name
(1S,3R)-3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-1H-naphtho[2,3-c]pyran-3-acetic acid, methyl ester
InChi Key
FMEUWIKCSICJBO-DTWKUNHWSA-N
InChi Code
InChI=1S/C17H16O6/c1-8-14-11(6-9(23-8)7-13(19)22-2)16(20)10-4-3-5-12(18)15(10)17(14)21/h3-5,8-9,18H,6-7H2,1-2H3/t8-,9+/m0/s1
SMILES Code
OC1=C2C(C(C(C[C@H](CC(OC)=O)O[C@H]3C)=C3C2=O)=O)=CC=C1
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
Biological target:
OM173-αA is a quinone bacterial metabolite that inhibits the growth of the bacteria M. gallisepticum, M. pneumoniae, and S. aureus.
In vitro activity:
Antibiotic OM-173 components alpha A, alpha E, alpha B, beta A and beta E were isolated from the fermentation broth of strain OM-173 by solvent extraction, silica gel chromatography and preparative thin-layer chromatography. The components are active against mycoplasmas and to a lesser extent against fungi. Strain OM-173 was identified as a strain of genus Streptomyces and differed apparently from Streptomyces rosa var. notoensis, the nanaomycin-producing strain, in cultural characteristics.
Reference: J Antibiot (Tokyo). 1983 Oct;36(10):1268-74. https://pubmed.ncbi.nlm.nih.gov/6643276/
|
Solvent |
mg/mL |
mM |
| Solubility |
| Ethanol |
1.0 |
3.16 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
316.31
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 |
Formulation protocol:
Iwai Y, Kimura K, Takahashi Y, Hinotozawa K, Shimizu H, Tanaka H, Omura S. OM-173, new nanaomycin-type antibiotics produced by a strain of Streptomyces. Taxonomy, production, isolation and biological properties. J Antibiot (Tokyo). 1983 Oct;36(10):1268-74. doi: 10.7164/antibiotics.36.1268. PMID: 6643276.
In vitro protocol:
Iwai Y, Kimura K, Takahashi Y, Hinotozawa K, Shimizu H, Tanaka H, Omura S. OM-173, new nanaomycin-type antibiotics produced by a strain of Streptomyces. Taxonomy, production, isolation and biological properties. J Antibiot (Tokyo). 1983 Oct;36(10):1268-74. doi: 10.7164/antibiotics.36.1268. PMID: 6643276.
1. Iwai, Y., Kimura, K., Takahashi, Y., et al. OM-173, new nanaomycin-type antibiotics produced by a strain of Streptomyces. Taxonomy, production, isolation and biological properties. J. Antibiot. (Tokyo) 36(10), 1268-1274 (1983).
2. Liu, C., Lei, H., Chen, X., et al. Four new nanaomycins produced by Streptomyces hebeiensis derived from lichen. Chem. Biodivers. 14(7), (2017).
3: Kakinuma S, Takada Y, Ikeda H, Tanaka H, Omura S, Hopwood DA. Cloning of large DNA fragments, which hybridize with actinorhodin biosynthesis genes, from kalafungin and nanaomycin A methyl ester producers and identification of genes for kalafungin biosynthesis of the kalafungin producer. J Antibiot (Tokyo). 1991 Sep;44(9):995-1005. doi: 10.7164/antibiotics.44.995. PMID: 1938623.
