eremomycin   Click here for help

GtoPdb Ligand ID: 10959

Synonyms: A82846A
Comment: Eremomycin (A82846A) is a glycopeptide, parenteral antibiotic with Gram-negative activity that was isolated from Actinomycete strain INA-238 [1]. It was discovered to be highly toxic in vivo, but a derivative was subsequently developed as oritavancin.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 30
Hydrogen bond donors 20
Rotatable bonds 16
Topological polar surface area 574.97
Molecular weight 1556.56
XLogP 0.01
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES OC[C@H]1O[C@@H](Oc2c3Oc4ccc(cc4)[C@@H](O[C@@H]4O[C@@H](C)[C@@H]([C@@](C4)(C)N)O)[C@@H]4NC(=O)[C@H](NC(=O)[C@H]5c(c3)cc2Oc2ccc(cc2Cl)[C@@H](O)[C@H](C(=O)N[C@H](C(=O)N5)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)c2ccc(c(c2)c2c([C@H](NC4=O)C(=O)O)cc(cc2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@@](C1)(C)N)O
Isomeric SMILES OC[C@H]1O[C@@H](Oc2c3Oc4ccc(cc4)[C@@H](O[C@@H]4O[C@@H](C)[C@@H]([C@@](C4)(C)N)O)[C@@H]4NC(=O)[C@H](NC(=O)[C@H]5c(c3)cc2Oc2ccc(cc2Cl)[C@@H](O)[C@H](C(=O)N[C@H](C(=O)N5)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)c2ccc(c(c2)c2c([C@H](NC4=O)C(=O)O)cc(cc2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@@](C1)(C)N)O
InChI InChI=1S/C73H89ClN10O26/c1-27(2)16-39(78-7)64(95)83-54-56(90)32-11-15-43(38(74)18-32)106-45-20-33-19-44(60(45)110-71-61(58(92)57(91)46(26-85)107-71)109-49-25-73(6,77)63(94)29(4)104-49)105-35-12-8-30(9-13-35)59(108-48-24-72(5,76)62(93)28(3)103-48)55-69(100)82-53(70(101)102)37-21-34(86)22-42(88)50(37)36-17-31(10-14-41(36)87)51(66(97)84-55)81-67(98)52(33)80-65(96)40(23-47(75)89)79-68(54)99/h8-15,17-22,27-29,39-40,46,48-49,51-59,61-63,71,78,85-88,90-94H,16,23-26,76-77H2,1-7H3,(H2,75,89)(H,79,99)(H,80,96)(H,81,98)(H,82,100)(H,83,95)(H,84,97)(H,101,102)/t28-,29-,39+,40-,46+,48-,49-,51+,52+,53-,54+,55-,56+,57+,58-,59+,61+,62-,63-,71-,72-,73-/m0/s1
InChI Key UECIPBUIMXSXEI-BNSVOVDNSA-N
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InChI standard identifier Download
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Molecular structure representations generated using Open Babel