cervimycin C   Click here for help

GtoPdb Ligand ID: 13603

Compound class: Natural product
Comment: Cervimycin C is the major component of a complex of aromatic polyketide glycosides produced by Streptomyces tendae HKI-179 [3]. It demonstrates potent antibacterial activity against Gram-positive spp., including drug-resistant pathogens [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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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 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.

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Hydrogen bond acceptors 26
Hydrogen bond donors 5
Rotatable bonds 18
Topological polar surface area 355.65
Molecular weight 1228.29
XLogP 3.99
No. Lipinski's rules broken 3

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
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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 C[C@@H]1[C@H](CC[C@@H](O1)O[C@H]2CC[C@@H](O[C@@H]2C)O[C@]34[C@H](CC5=C(C(=C6C(=C5)C(=O)C(=CC6=O)OC)O)C3=O)[C@H](C(=O)C(=C4O)C(=O)N)O[C@H]7CC[C@@H]([C@@H](C)O7)O[C@H]8CC[C@@H]([C@H](C)O8)O[C@H]9CC[C@@H]([C@H](C)O9)O[C@H]%10CC[C@@H]([C@H](C)O%10)OC(=O)C(C)(C)C(=O)O)O
Isomeric SMILES C[C@@H]1[C@H](CC[C@@H](O1)O[C@H]2CC[C@@H](O[C@@H]2C)O[C@]34[C@H](CC5=CC6=C(C(=O)C=C(C6=O)OC)C(=C5C3=O)O)[C@H](C(=O)C(=C4O)C(=O)N)O[C@H]7CC[C@@H]([C@H](O7)C)O[C@H]8CC[C@@H]([C@@H](O8)C)O[C@H]9CC[C@@H]([C@@H](O9)C)O[C@H]%10CC[C@@H]([C@@H](O%10)C)OC(=O)C(C)(C)C(=O)O)O
InChI InChI=1S/C61H81NO25/c1-25-34(63)10-16-42(75-25)81-39-15-21-47(80-29(39)5)87-61-33(23-31-22-32-49(52(66)48(31)55(61)68)35(64)24-41(74-9)51(32)65)54(53(67)50(56(61)69)57(62)70)86-46-20-13-38(28(4)79-46)84-44-18-11-36(26(2)77-44)82-43-17-12-37(27(3)76-43)83-45-19-14-40(30(6)78-45)85-59(73)60(7,8)58(71)72/h22,24-30,33-34,36-40,42-47,54,63,66,69H,10-21,23H2,1-9H3,(H2,62,70)(H,71,72)/t25-,26+,27+,28-,29-,30+,33-,34+,36+,37+,38+,39+,40+,42+,43+,44+,45+,46+,47+,54-,61-/m1/s1
InChI Key CYKZTBKVWQAQLU-KSQSWLAPSA-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. Dietrich A, Steffens U, Gajdiss M, Boschert AL, Dröge JK, Szekat C, Sass P, Malik IT, Bornikoel J, Reinke L et al.. (2022)
Cervimycin-Resistant Staphylococcus aureus Strains Display Vancomycin-Intermediate Resistant Phenotypes.
Microbiol Spectr, 10 (5): e0256722. [PMID:36173303]
2. Herold K, Gollmick FA, Groth I, Roth M, Menzel KD, Möllmann U, Gräfe U, Hertweck C. (2005)
Cervimycin A-D: a polyketide glycoside complex from a cave bacterium can defeat vancomycin resistance.
Chemistry, 11 (19): 5523-30. [PMID:15940739]
3. Herold K, Xu Z, Gollmick FA, Grafe U, Hertweck C. (2004)
Biosynthesis of cervimycin C, an aromatic polyketide antibiotic bearing an unusual dimethylmalonyl moiety.
Org Biomol Chem, 2 (17): 2411-4. [PMID:15326518]
4. Hoffmann A, Steffens U, Maček B, Franz-Wachtel M, Nieselt K, Harbig TA, Scherlach K, Hertweck C, Sahl H-G, Bierbaum G. (2024)
The unusual mode of action of the polyketide glycoside antibiotic cervimycin C.
mSphere, 9 (5): e0076423. [PMID:38722162]