Compound ID | 2251

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Sphaerimicin analogue

Synonym(s): SPM-1  |  SPM-2  |  SPM-3

Class: Small molecule antibacterial agent

Spectrum of activity: Gram-positive
Details of activity: Active against Enterococcus faecium, Staphylococcus aureus, and Mycobacterium avium
Description: Synthetic compound rationally designed from core structure of sphaerimicin, a natural product from Sphaerisporangium sp. SANK60911
Year first mentioned: 2022
Development status: Experimental
Chemical structure(s):
SPM-2
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Molecular weight: 784.89
Iso. SMILES: CCCCCCCCCCCCCCCC(O[C@@H]1[C@H](O)C[N@]2[C@H](C(O)=O)[C@@H]([C@@H]3[C@H](O)[C@H](O)[C@H](N4C(NC(C=C4)=O)=O)O3)O[C@@H]5O[C@H](CN[C@@H]1C2)[C@H]([C@H]5O)O)=O
InChI Key: COFIPAYOUOZUCF-VGRYHQQISA-N
Can. SMILES: CCCCCCCCCCCCCCCC(=O)O[C@H]1[C@H]2C[N@@](C[C@H]1O)[C@@H]([C@@H]([C@@H]3[C@@H]([C@@H]([C@H](N4C=CC(=O)NC4=O)O3)O)O)O[C@H]5[C@@H]([C@@H]([C@@H](CN2)O5)O)O)C(=O)O
InChI: InChI=1S/C37H60N4O14/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-25(44)53-31-21-19-40(20-22(31)42)26(35(49)50)32(55-36-30(48)27(45)23(52-36)18-38-21)33-28(46)29(47)34(54-33)41-17-16-24(43)39-37(41)51/h16-17,21-23,26-34,36,38,42,45-48H,2-15,18-20H2,1H3,(H,49,50)(H,39,43,51)/t21-,22-,23-,26+,27-,28-,29+,30-,31+,32+,33+,34-,36+/m1/s1
SPM-1
Click here for structure editor
Molecular weight: 784.89
Iso. SMILES: CCCCCCCCCCCCCCCC(O[C@H]1[C@@H](O)C[N@]2[C@H](C(O)=O)[C@@H]([C@@H]3[C@H](O)[C@H](O)[C@H](N4C(NC(C=C4)=O)=O)O3)O[C@@H]5O[C@H](CN[C@H]1C2)[C@H]([C@H]5O)O)=O
InChI Key: COFIPAYOUOZUCF-BMTDXRFBSA-N
Can. SMILES: CCCCCCCCCCCCCCCC(=O)O[C@@H]1[C@@H]2C[N@@](C[C@@H]1O)[C@@H]([C@@H]([C@@H]3[C@@H]([C@@H]([C@H](N4C=CC(=O)NC4=O)O3)O)O)O[C@H]5[C@@H]([C@@H]([C@@H](CN2)O5)O)O)C(=O)O
InChI: InChI=1S/C37H60N4O14/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-25(44)53-31-21-19-40(20-22(31)42)26(35(49)50)32(55-36-30(48)27(45)23(52-36)18-38-21)33-28(46)29(47)34(54-33)41-17-16-24(43)39-37(41)51/h16-17,21-23,26-34,36,38,42,45-48H,2-15,18-20H2,1H3,(H,49,50)(H,39,43,51)/t21-,22-,23+,26-,27+,28+,29-,30+,31+,32-,33-,34+,36-/m0/s1
External links:
Citations:
  • https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.201305546
  • https://www.nature.com/articles/s41467-022-35227-z#Sec2

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