cyclohexylgriselimycin   Click here for help

GtoPdb Ligand ID: 13756

Synonyms: cyclohexyl-griselimycin
Compound class: Peptide
Comment: Cyclohexylgriselimycin is an optimized cyclohexyl analogue of griselimycin, a natural Streptomyces-derived cyclic peptide. Cyclohexylgriselimycin inhibits Mycobacterium tuberculosis beta sliding clamp (DnaN) [2] and has potent antimycobacterial activity [1-2].
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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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.

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/)

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Canonical SMILES CC(C)C[C@H]1C(=O)N(C)[C@@H](C(C)C)C(=O)N2C[C@@H](C[C@H]2C(=O)N(C)[C@H](CC(C)C)C(=O)NCC(=O)O[C@H](C)[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N3C[C@H](C)C[C@H]3C(=O)N1)N(C)C(=O)[C@@H]4C[C@@H](C)CN4C(=O)[C@H](C(C)C)N(C)C(=O)C)C5CCCCC5
Isomeric SMILES C[C@@H]1C[C@H]2C(=O)N[C@H](C(=O)N([C@H](C(=O)N3C[C@@H](C[C@H]3C(=O)N([C@@H](C(=O)NCC(=O)O[C@@H]([C@@H](C(=O)N[C@H](C(=O)N2C1)CC(C)C)N(C)C(=O)[C@@H]4C[C@H](CN4C(=O)[C@H](C(C)C)N(C)C(=O)C)C)C)CC(C)C)C)C5CCCCC5)C(C)C)C)CC(C)C
InChI InChI=1S/C63H106N10O12/c1-34(2)24-45-58(79)69(17)53(38(9)10)63(84)73-33-44(43-22-20-19-21-23-43)29-50(73)60(81)68(16)47(26-36(5)6)55(76)64-30-51(75)85-41(13)54(57(78)66-46(25-35(3)4)59(80)71-31-39(11)27-48(71)56(77)65-45)70(18)61(82)49-28-40(12)32-72(49)62(83)52(37(7)8)67(15)42(14)74/h34-41,43-50,52-54H,19-33H2,1-18H3,(H,64,76)(H,65,77)(H,66,78)/t39-,40-,41-,44-,45+,46+,47-,48+,49+,50+,52+,53+,54+/m1/s1
InChI Key QVJWQAABJRGBNE-JLLURPHASA-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/)
References
1. Aragaw WW, Roubert C, Fontaine E, Lagrange S, Zimmerman MD, Dartois V, Gengenbacher M, Dick T. (2022)
Cyclohexyl-griselimycin Is Active against Mycobacterium abscessus in Mice.
Antimicrob Agents Chemother, 66 (1): e0140021. [PMID:34723632]
2. Kling A, Lukat P, Almeida DV, Bauer A, Fontaine E, Sordello S, Zaburannyi N, Herrmann J, Wenzel SC, König C et al.. (2015)
Antibiotics. Targeting DnaN for tuberculosis therapy using novel griselimycins.
Science, 348 (6239): 1106-12. [PMID:26045430]