| Identification | Back Directory | [Name]
napyradiomycin A1 | [CAS]
103106-24-7 | [Synonyms]
WS-9558A
Napyradiomycin A
napyradiomycin A1
3,4a-Dichloro-6,8-dihydroxy-3,4,4a,10a-tetrahydro-2,2-dimethyl-10a-(3,7-dimethyl-2,6-octadienyl)-2H-naphtho[2,3-b]pyran-5,10-dione
2H-Naphtho[2,3-b]pyran-5,10-dione, 3,4a-dichloro-10a-[(2E)-3,7-dimethyl-2,6-octadien-1-yl]-3,4,4a,10a-tetrahydro-6,8-dihydroxy-2,2-dimethyl-, (3R,4aR,10aS)- | [Molecular Formula]
C25H30Cl2O5 | [MDL Number]
MFCD01712236 | [MOL File]
103106-24-7.mol | [Molecular Weight]
481.41 |
| Chemical Properties | Back Directory | [Boiling point ]
642.5±55.0 °C(Predicted) | [density ]
1.31±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
Dichloromethane: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble | [form ]
A solid | [pka]
6.14±0.70(Predicted) |
| Safety Data | Back Directory | [HS Code ]
29419000 | [Toxicity]
mouse,LD50,intraperitoneal,> 250mg/kg (250mg/kg),Journal of Antibiotics. Vol. 39, Pg. 487, 1986. |
| Hazard Information | Back Directory | [Description]
Napyradiomycin A1 is a fungal metabolite originally isolated from C. rubra and has diverse biological activities. It is active against S. aureus, M. luteus, B. anthracis, C. bovis, and M. smegmatis (MICs = 1.56-12.5 μg/ml). Napyradiomycin A1 is an estrogen receptor antagonist (IC50 = 4.2 μM in rat uterine homogenates). It also inhibits mitochondrial NADH:ubiquinone oxidoreductase (complex I) and succinate:ubiquinone oxidoreductase (complex II) activities in bovine heart homogenates (IC50s = 20 and 9.7 μM, respectively). | [Uses]
Napyradiomycin derivatives have antibacterial and tumor properties. Napyradiomycin A1 is a secondary metabolite isolated from Streptomyces. It is also an antibacterial antibiotic and an inhibitor of mitochondrial complexes I and II. | [Definition]
ChEBI: Napyradiomycin A1 is a member of menaquinones. | [References]
[1] K SHIOMI. Novel antibiotics napyradiomycins. Production, isolation, physico-chemical properties and biological activity.[J]. Journal of Antibiotics, 1986, 39 4: 487-493. DOI: 10.7164/antibiotics.39.487
[2] Y HORI. Napyradiomycins A and B1: non-steroidal estrogen-receptor antagonists produced by a Streptomyces.[J]. Journal of Antibiotics, 1993, 46 12: 1890-1893. DOI: 10.7164/antibiotics.46.1890
[3] KOHTA YAMAMOTO. Napyradiomycin A1, an inhibitor of mitochondrial complexes I and II[J]. Journal of Antibiotics, 2012, 65 4: 211-214. DOI: 10.1038/ja.2011.138 |
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