A-80915 C

A-80915 C

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Category Antibiotics
Catalog number BBF-03169
CAS 127875-62-1
Molecular Weight 547.89
Molecular Formula C26H33Cl3O6

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Description

A-80915 C is a naphthoquinone antibiotic produced by Streptomyces aculeolatus A80915. Activity against gram-positive bacteria.

Specification

Synonyms 3,4a-dichloro-10a-(3-chloro-6-hydroxy-2,2,6-trimethyl-cyclohexylmethyl)-6,8-dihydroxy-2,2,7-trimethyl-3,4,4a,10a-tetrahydro-2H-benzo[g]chromene-5,10-dione
IUPAC Name (3R,4aR,10aS)-3,4a-dichloro-10a-[[(1S,3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl]-6,8-dihydroxy-2,2,7-trimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione
Canonical SMILES CC1=C(C=C2C(=C1O)C(=O)C3(CC(C(OC3(C2=O)CC4C(C(CCC4(C)O)Cl)(C)C)(C)C)Cl)Cl)O
InChI InChI=1S/C26H33Cl3O6/c1-12-14(30)9-13-18(19(12)31)21(33)25(29)11-17(28)23(4,5)35-26(25,20(13)32)10-15-22(2,3)16(27)7-8-24(15,6)34/h9,15-17,30-31,34H,7-8,10-11H2,1-6H3/t15-,16-,17+,24-,25-,26-/m0/s1
InChI Key XGGIVXWAYKZBIV-CYGDAPSSSA-N

Properties

Appearance Yellow Crystal
Antibiotic Activity Spectrum Gram-positive bacteria
Density 1.32 g/cm3

Reference Reading

1. A80915, a new antibiotic complex produced by Streptomyces aculeolatus. Discovery, taxonomy, fermentation, isolation, characterization, and antibacterial evaluation
D S Fukuda, J S Mynderse, P J Baker, D M Berry, L D Boeck, R C Yao, F P Mertz, W M Nakatsukasa, J Mabe, J Ott, et al. J Antibiot (Tokyo). 1990 Jun;43(6):623-33. doi: 10.7164/antibiotics.43.623.
New semi-naphthaquinone antibiotics A80915A, B, C, and D were isolated from the fermented broth of Streptomyces aculeolatus A80915 (NRRL 18422). Factors A and C, present in both the broth filtrate and mycelial methanol extract, and factors B and D, found predominantly in the broth filtrate, were recovered by extraction with ethyl acetate. Purification of the individual factors was accomplished by preparative reverse phase high performance liquid chromatograph on C18 bonded silica supports. Factors A through D show antimicrobial activity against Gram-positive aerobic and anaerobic organisms in vitro. Mechanism of action studies demonstrated nearly complete inhibition of macromolecular biosynthesis (protein, RNA, DNA, and cell wall) by A80915 factors A through D. A less highly cyclized semi-naphthaquinone, A80915 factor G, was isolated from the broth of the strain fermented in an alternate medium.
2. TMKS8A, an antibacterial and cytotoxic chlorinated α-lapachone, from a sea slug-derived actinomycete of the genus Streptomyces
Zhiwei Zhang, Mada Triandala Sibero, Akiho Kai, Keisuke Fukaya, Daisuke Urabe, Yasuhiro Igarashi J Antibiot (Tokyo). 2021 Jul;74(7):464-469. doi: 10.1038/s41429-021-00415-4. Epub 2021 Mar 11.
TMKS8A (1), a new chlorinated α-lapachone derivative, along with five known related metabolites, A80915 C (2), SF2415B1 (3), chlorinated dihydroquinone 3 (4), SF2415B3 (5), and A80915 C (6), were identified from the culture extract of Streptomyces sp. TMKS8, which was isolated from a sea slug, Paromoionchis tumidus. The structure of 1 was determined by the analysis of NMR and MS spectral data, assisted by NMR chemical shift prediction using DFT-based calculation. The absolute configuration was determined to be R by comparison of experimental and calculated ECD spectra. Compound 1 displayed antimicrobial activity against Gram-positive bacteria with MIC values ranging from 6.25 to 12.5 μg ml-1 and cytotoxicity against murine leukemia P388 cells with IC50 9.8 μM.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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