upleganan

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Ligands
upleganan

GtoPdb Ligand ID: 12797

Synonyms: compound 44 [PMID: 31525992] | EVER206 | SPR206

Compound class: Synthetic organic

Comment: Upleganan (SPR206) is a polymyxin antibacterial with activity against multidrug-resistant (MDR) Gram-negative species, together with lower nephrotoxicity than polymyxin B [1].

2D Structure

Physico-chemical Properties

Hydrogen bond acceptors	27
Hydrogen bond donors	17
Rotatable bonds	25
Topological polar surface area	461.56
Molecular weight	1144.76
XLogP	-1.47
No. Lipinski's rules broken	4

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey

Canonical 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
Isomeric SMILES	C([C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCN)C(=O)N[C@@H](CCN)C(=O)N[C@@]([C@@H](C)O)(C(=O)NCC[C@H](NC([C@@H](NC([C@@H](NC(C[C@H](CN)C2=CC(Cl)=CC=C2)=O)[C@@H](C)O)=O)CN)=O)C(=O)N[C@@H](CCN)C(=O)N1)[H])C3=CC=CC=C3
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
InChI Key	VAZVBVUQVUHPMS-DFEDBOKMSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)