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
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were 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/). 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.

✖
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
Click here for help

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.

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/)

✖
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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2S,3R)-2-[[(3S)-4-amino-3-(3-chlorophenyl)butanoyl]amino]-N-[(2S)-3-amino-1-oxo-1-[[(3S,6S,9S,12S,15R,18S,21S)-6,9,18-tris(2-aminoethyl)-15-benzyl-3-[(1R)-1-hydroxyethyl]-12-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]propan-2-yl]-3-hydroxybutanamide
International Nonproprietary Names Click here for help
INN number INN
12524 upleganan
Synonyms Click here for help
compound 44 [PMID: 31525992] | EVER206 | SPR206
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Upleganan
Other databases
CAS Registry No. 2407717-17-1 (source: Scifinder)
GtoPdb PubChem SID 483123345
PubChem CID 139600308
Search Google for chemical match using the InChIKey VAZVBVUQVUHPMS-DFEDBOKMSA-N
Search Google for chemicals with the same backbone VAZVBVUQVUHPMS
Search PubMed clinical trials upleganan
Search PubMed titles upleganan
Search PubMed titles/abstracts upleganan
UniChem Compound Search for chemical match using the InChIKey VAZVBVUQVUHPMS-DFEDBOKMSA-N
UniChem Connectivity Search for chemical match using the InChIKey VAZVBVUQVUHPMS-DFEDBOKMSA-N