picromycin

Also known as Amaromycin, Antibiotic B 62169A, Albomycetin

Pikromycin was studied by Brokmann and Hekel in 1951 and was the first antibiotic macrolide to be isolated. Pikromycin is synthesized through a type I polyketide synthase system in Streptomyces venezuelae, a species of Gram-positive bacterium in the genus Streptomyces. Pikromycin is derived from narbonolide, a 14-membered ring macrolide. Along with the narbonolide backbone, pikromycin includes a desosamine sugar and a hydroxyl group. Although Pikromycin is not a clinically useful antibiotic, it can be used as a raw material to synthesize antibiotic ketolide compounds such as erythromycins and

In the Vinony graph

Vinony's link graph records 4 inbound references to picromycin, and connects out to digital object identifier, chemical formula and molar mass.

It is catalogued under the topic Macrolide antibiotics.

Vinony links it to 5 Wikipedia language editions.

Chemical data

Formula: C28H47NO8
Molecular weight: 525.7 g/mol
IUPAC name: (3R,5R,6S,7S,9R,11E,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-13-hydroxy-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11-ene-2,4,10-trione
SMILES: CC[C@@H]1[C@@](/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H](C(=O)[C@H](C(=O)O1)C)C)O[C@H]2[C@@H]([C@H](C[C@H](O2)C)N(C)C)O)C)C)(C)O
InChIKey: UZQBOFAUUTZOQE-VSLWXVDYSA-N
XLogP: 3.2
Polar surface area: 123 Å²
H-bond donors: 2
H-bond acceptors: 9
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: macrolides
Mass: 525.330167

Show 3 more facts

chemical formula: C₂₈H₄₇NO₈
canonical SMILES: CCC1C(C=CC(=O)C(CC(C(C(C(=O)C(C(=O)O1)C)C)OC2C(C(CC(O2)C)N(C)C)O)C)C)(C)O
isomeric SMILES: CC[C@@H]1[C@@](/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H](C(=O)[C@H](C(=O)O1)C)C)O[C@H]2[C@@H]([C@H](C[C@H](O2)C)N(C)C)O)C)C)(C)O

Sources (2)

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Encyclopedic overview

3 sections

Contents

Biosynthesis
See also
References

{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 450797983 | ImageFile =Pikromycin.svg | ImageSize = | IUPACName = (3R,5R,6S,7S,9R,11E,13S,14R)-14-Ethyl-13-hydroxy-3,5,7,9,13-pentamethyl-6-[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyloxy]-1-oxacyclotetradec-11-ene-2,4,10-trione | SystematicName = (3R,5R,6S,7S,9R,11E,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-13-hydroxy-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11-ene-2,4,10-trione | OtherNames = Picromycin |Section1= |Section2= |Section3= }}

Excerpted from Wikipedia’s “picromycin” article, available under the CC BY-SA 4.0 licence.