upleganan   Click here for help

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 multi-drug resistant (MDR) Gram-negative species, together with lower nephrotoxicity than polymyxin B [1].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
References
1. Brown P, Abbott E, Abdulle O, Boakes S, Coleman S, Divall N, Duperchy E, Moss S, Rivers D, Simonovic M et al.. (2019)
Design of Next Generation Polymyxins with Lower Toxicity: The Discovery of SPR206.
ACS Infect Dis, 5 (10): 1645-1656. [PMID:31525992]
2. Bruss J, Lister T, Gupta VK, Stone E, Morelli L, Lei Y, Melnick D. (2021)
Single- and Multiple-Ascending-Dose Study of the Safety, Tolerability, and Pharmacokinetics of the Polymyxin Derivative SPR206.
Antimicrob Agents Chemother, 65 (10): e0073921. [PMID:34339267]
3. Rodvold KA, Bader J, Bruss JB, Hamed K. (2023)
Pharmacokinetics of SPR206 in Plasma, Pulmonary Epithelial Lining Fluid, and Alveolar Macrophages following Intravenous Administration to Healthy Adult Subjects.
Antimicrob Agents Chemother, 67 (7): e0042623. [PMID:37338378]
4. Zhang Y, Zhao C, Wang Q, Wang X, Chen H, Li H, Zhang F, Wang H. (2020)
Evaluation of the in vitro activity of new polymyxin B analogue SPR206 against clinical MDR, colistin-resistant and tigecycline-resistant Gram-negative bacilli.
J Antimicrob Chemother, 75 (9): 2609-2615. [PMID:32591806]