Compound ID | 2122

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Swalpamycin

Class: Macrolide

Spectrum of activity: Gram-positive
Details of activity: Binds to the peptidyl transferase component of the 50S subunit of ribosomes, thus inhibiting peptide bond formation and bacterial protein synthesis. It is active against Gram-positive bacteria.
Description: Natural product produced by Streptomyces, synthetic production. Systemic and topical application.
Institute where first reported: Hoechst AG
Year first mentioned: 1987
Development status: Experimental
Chemical structure(s):
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Molecular weight: 724.83
Iso. SMILES: C[C@H]1C[C@H](C(=O)/C=C/C=C/[C@@H]([C@H](OC(=O)/C=C/[C@@H]([C@H]1O[C@H]2[C@@H](C3(C[C@H](O2)C)[C@@H](OC(=O)O3)C)O)C)C)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@H](O4)C)O)OC)OC)C
InChI Key: AAUZLHJDJNJJDM-VYBYGPFESA-N
Can. SMILES: C[C@H]1/C=C/C(=O)O[C@H](C)[C@H](/C=C/C=C/C(=O)[C@H](C)C[C@H](C)[C@@H]1O[C@H]2[C@@H](C3(C[C@@H](C)O2)[C@H](C)OC(=O)O3)O)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@@H](C)O4)O)OC)OC
InChI: InChI=1S/C37H56O14/c1-19-14-15-28(39)47-23(5)26(18-45-34-32(44-9)31(43-8)29(40)24(6)48-34)12-10-11-13-27(38)20(2)16-21(3)30(19)50-35-33(41)37(17-22(4)46-35)25(7)49-36(42)51-37/h10-15,19-26,29-35,40-41H,16-18H2,1-9H3/b12-10+,13-11+,15-14+/t19-,20+,21-,22+,23+,24+,25-,26+,29+,30+,31+,32+,33-,34+,35-,37?/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/24884121
Citations:
  • https://www.jstage.jst.go.jp/article/antibiotics1968/40/10/40_10_1368/_pdf/-char/en
  • https://www.jstage.jst.go.jp/article/antibiotics1968/40/10/40_10_1361/_pdf/-char/en

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