Compound ID | 1232

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Upleganan

Synonym(s): SPR206  |  EVER206

Class: Polymyxin

Details of activity: Disrupts the outer membrane by direct interaction with the lipid A component of the LPS and and disrupts the physical integrity of the phospholipid bilayer of the inner membrane, and possibly additional modes of action.
Combined with other compounds: Yes
Institute where first reported: Spero Therapeutics
Highest development stage: Phase 1
Development status: Active
Chemical structure(s):
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Molecular weight: 1144.76
Iso. SMILES: C[C@H]([C@H]1C(=O)NCC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCN)CCN)CC(C)C)CC2=CC=CC=C2)CCN)NC(=O)[C@H](CN)NC(=O)[C@H]([C@@H](C)O)NC(=O)C[C@H](CN)C3=CC(=CC=C3)Cl)O
InChI Key: VAZVBVUQVUHPMS-DFEDBOKMSA-N
Can. SMILES: CC(C)C[C@H]1C(=O)N[C@@H](CCN)C(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC[C@@H](C(=O)N[C@@H](CCN)C(=O)N[C@H](CC2=CC=CC=C2)C(=O)N1)NC(=O)[C@H](CN)NC(=O)[C@H]([C@@H](C)O)NC(=O)C[C@H](CN)C3=CC=CC(=C3)Cl
InChI: InChI=1S/C52H82ClN15O12/c1-27(2)21-38-48(76)62-34(13-17-54)44(72)61-36(15-19-56)47(75)68-42(28(3)69)51(79)59-20-16-37(46(74)60-35(14-18-55)45(73)65-39(49(77)64-38)22-30-9-6-5-7-10-30)63-50(78)40(26-58)66-52(80)43(29(4)70)67-41(71)24-32(25-57)31-11-8-12-33(53)23-31/h5-12,23,27-29,32,34-40,42-43,69-70H,13-22,24-26,54-58H2,1-4H3,(H,59,79)(H,60,74)(H,61,72)(H,62,76)(H,63,78)(H,64,77)(H,65,73)(H,66,80)(H,67,71)(H,68,75)/t28-,29-,32-,34+,35+,36+,37+,38+,39-,40+,42+,43+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/139600308
Guide to Pharmacology: upleganan
Citations:
  • https://7kh1s27nul32laip2jdnb518-wpengine.netdna-ssl.com/wp-content/uploads/2018/09/ESCMID-80.pdf
  • https://aac.asm.org/content/63/10/e00935-19
  • https://academic.oup.com/jac/article-abstract/doi/10.1093/jac/dkaa217/5863535?redirectedFrom=fulltext

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