O-Demethylpaulomycin A
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| Category | Antibiotics |
| Catalog number | BBF-00830 |
| CAS | 113603-74-0 |
| Molecular Weight | 772.77 |
| Molecular Formula | C33H44N2O17S |
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Description
O-Demethylpaulomycin A is a quinone antibiotic produced by Streptomyces paulus. It has the effect of anti-gram-positive bacteria, and its activity is lower than that of Pauloycin.
Specification
| Synonyms | 5-[6-(acetyloxymethyl)-4-[4,5-dihydroxy-6-methyl-5-[1-(2-methylbutanoyloxy)ethyl]oxan-2-yl]oxy-3-hydroxy-5-[(E)-2-isothiocyanatobut-2-enoyl]oxyoxan-2-yl]-2-amino-5-hydroxy-3,6-dioxocyclohexene-1-carboxylic acid; 1-Cyclohexene-1-carboxylic acid, 5-(6-O-acetyl-3-O-(2,6-dideoxy-4-C-((S(S))-1-(2-methyl-1-oxobutoxy)ethyl)-alpha-L-lyxo-hexopyranosyl)-4-O-((Z)-2-isothiocyanato-1-oxo-2-butenyl)-beta-D-allopyranosyl)-2-amino-5-hydroxy-3,6-dioxo-, (S)- |
| IUPAC Name | 3-[6-(acetyloxymethyl)-4-[4,5-dihydroxy-6-methyl-5-[1-(2-methylbutanoyloxy)ethyl]oxan-2-yl]oxy-3-hydroxy-5-[(E)-2-isothiocyanatobut-2-enoyl]oxyoxan-2-yl]-2,3-dihydroxy-6-imino-5-oxocyclohexene-1-carboxylic acid |
| Canonical SMILES | CCC(C)C(=O)OC(C)C1(C(OC(CC1O)OC2C(C(OC(C2OC(=O)C(=CC)N=C=S)COC(=O)C)C3(CC(=O)C(=N)C(=C3O)C(=O)O)O)O)C)O |
| InChI | InChI=1S/C33H44N2O17S/c1-7-13(3)30(43)49-15(5)33(46)14(4)48-21(9-20(33)38)51-26-24(39)28(32(45)10-18(37)23(34)22(27(32)40)29(41)42)50-19(11-47-16(6)36)25(26)52-31(44)17(8-2)35-12-53/h8,13-15,19-21,24-26,28,34,38-40,45-46H,7,9-11H2,1-6H3,(H,41,42)/b17-8+,34-23? |
| InChI Key | MMHXEYFKFMVGKP-MIRXUTFGSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 899.9°C at 760 mmHg |
| Density | 1.54 g/cm3 |
Reference Reading
1. O-demethylpaulomycins A and B, U-77,802 and U-77,803, paulomenols A and B, new metabolites produced by Streptomyces paulus
A D Argoudelis, L Baczynskyj, S A Mizsak, F B Shilliday J Antibiot (Tokyo). 1988 Oct;41(10):1316-30. doi: 10.7164/antibiotics.41.1316.
O-Demethylpaulomycin A (C33H44N2O17S), O-demethylpaulomycin B (C32H42N2O17S), paulomenol A (C29H43NO16), paulomenol B (C28H41NO16), and the hydrogen sulfide adducts of paulomycin A (U-77,802, C34H48N2O17S2), and paulomycin B (U-77,803, C33H46N2O17S2) have been isolated from fermentations of Streptomyces paulus strain 273. The structure of these compounds was determined by 1H and 13C NMR and fast atom bombardment mass spectrum spectroscopic techniques and degradative studies. The antibacterial properties of these new metabolites, which are related to paulomycins A and B (J. Antibiotics 35: 285-294, 1982), are briefly discussed.
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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 ╳
