A 39183A
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| Category | Antibiotics |
| Catalog number | BBF-04211 |
| CAS | 79426-51-0 |
| Molecular Weight | 598.60 |
| Molecular Formula | C34H30O10 |
| Purity | >95% by HPLC |
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Description
It is an anthraquinone antibiotic produced by the strain of streptomyces sp. It has broad spectrum antimicrobial activity against both sensitive and resistant strains, including many anaerobic bacteria. It also has the activity against gram-positive and gram-negative bacteria.
Specification
| Synonyms | Antibiotic A 39183A; (1S,1'S,2S,2'S)-1,1'-Diacetyl-2,2',5,5',10,10'-hexahydroxy-2,2'-dimethyl-2,2',3,3'-tetrahydro-9,9'-bianthracene-4,4'(1H,1'H)-dione |
| Storage | Store at -20°C |
| IUPAC Name | (3S,4S)-4-acetyl-10-[(1S,2S)-1-acetyl-2,5,10-trihydroxy-2-methyl-4-oxo-1,3-dihydroanthracen-9-yl]-3,8,9-trihydroxy-3-methyl-2,4-dihydroanthracen-1-one |
| Canonical SMILES | CC(=O)C1C2=C(C3=C(C(=CC=C3)O)C(=C2C(=O)CC1(C)O)O)C4=C5C(C(CC(=O)C5=C(C6=C4C=CC=C6O)O)(C)O)C(=O)C |
| InChI | InChI=1S/C34H30O10/c1-13(35)29-27-23(15-7-5-9-17(37)21(15)31(41)25(27)19(39)11-33(29,3)43)24-16-8-6-10-18(38)22(16)32(42)26-20(40)12-34(4,44)30(14(2)36)28(24)26/h5-10,29-30,37-38,41-44H,11-12H2,1-4H3/t29-,30-,33-,34-/m0/s1 |
| InChI Key | HLVSLAAHFAXHHP-ANFUHZJESA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Yellow Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 790.1±60.0°C at 760 mmHg |
| Density | 1.5±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Dimeric Tetrahydroanthracene Regioisomers and Their Monomeric Precursor Produced by Streptomyces fumigatiscleroticus HDN10255
Haotian Wang, Tianjiao Zhu, Qianqun Gu, Qian Che, Dehai Li, Guojian Zhang, Yingqiang Wu, Chunxiao Sun, Junxiao Wang, Fenge Li J Nat Prod . 2020 Sep 25;83(9):2797-2802. doi: 10.1021/acs.jnatprod.0c00805.
Four new tetrahydroanthracene derivatives (1,3-5) and a known antibiotic, A-39183A (2), were discovered from the marine-sponge-derived actinomyceteStreptomyces fumigatiscleroticusHDN10255. Their structures including absolute configurations were elucidated based upon MS and NMR spectroscopic data, ECD calculations, and biogenetic considerations. Compounds2and4showed considerable cytotoxicity with the best IC50value of 1.8 μM against HeLa cells.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
