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kibdelomycin A   Click here for help

GtoPdb Ligand ID: 11016

Compound class: Natural product
Comment: Kibdelomycin is a broad-spectrum bactericidal agent with activity against aerobic bacteria [1]. It inhibits bacterial growth by inhibiting the bacterial DNA replication enzymes DNA gyrase and topoisomerase IV.
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 17
Hydrogen bond donors 6
Rotatable bonds 14
Topological polar surface area 258.5
Molecular weight 924.33
XLogP 4.15
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 CO[C@H]1[C@@H](OC(=O)C)[C@@H](OC(=O)N)[C@H](O[C@@H]1N1C(=O)/C(=C(/C2[C@@H](C)C=C[C@@H]3[C@@H]2C(=C)CC[C@H]3O[C@@H]2O[C@H](C)[C@H]([C@](C2)(O)[C@@H](NC(=O)c2[nH]cc(c2Cl)Cl)C)O)\O)/C(=O)[C@@H]1C(C)C)C
Isomeric SMILES CO[C@H]1[C@@H](OC(=O)C)[C@@H](OC(=O)N)[C@H](O[C@@H]1N1C(=O)/C(=C(/C2[C@@H](C)C=C[C@@H]3[C@@H]2C(=C)CC[C@H]3O[C@@H]2O[C@H](C)[C@H]([C@](C2)(O)[C@@H](NC(=O)c2[nH]cc(c2Cl)Cl)C)O)\O)/C(=O)[C@@H]1C(C)C)C
InChI InChI=1S/C43H58Cl2N4O14/c1-16(2)32-34(52)29(40(55)49(32)41-37(58-9)36(61-22(8)50)35(19(5)60-41)63-42(46)56)33(51)28-18(4)10-12-23-25(13-11-17(3)27(23)28)62-26-14-43(57,38(53)20(6)59-26)21(7)48-39(54)31-30(45)24(44)15-47-31/h10,12,15-16,18-21,23,25-28,32,35-38,41,47,51,53,57H,3,11,13-14H2,1-2,4-9H3,(H2,46,56)(H,48,54)/b33-29-/t18-,19+,20+,21-,23-,25+,26-,27-,28?,32-,35-,36-,37-,38+,41-,43+/m0/s1
InChI Key ZPMXCTSMZFCELU-DEIVJSAASA-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 Natural product
IUPAC Name Click here for help
[(2S,3S,4S,5S,6R)-2-[(3Z,5S)-3-[[(2S,4aR,5R,8aS)-5-[(2R,4R,5R,6R)-4-[(1S)-1-[(3,4-dichloro-1H-pyrrole-2-carbonyl)amino]ethyl]-4,5-dihydroxy-6-methyloxan-2-yl]oxy-2-methyl-8-methylidene-2,4a,5,6,7,8a-hexahydro-1H-naphthalen-1-yl]-hydroxymethylidene]-2,4-dioxo-5-propan-2-ylpyrrolidin-1-yl]-5-carbamoyloxy-3-methoxy-6-methyloxan-4-yl] acetate
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Kibdelomycin
Other databases
ChEMBL Ligand CHEMBL2205317
GtoPdb PubChem SID 405560457
PubChem CID 71457656
Search Google for chemical match using the InChIKey ZPMXCTSMZFCELU-DEIVJSAASA-N
Search Google for chemicals with the same backbone ZPMXCTSMZFCELU
UniChem Compound Search for chemical match using the InChIKey ZPMXCTSMZFCELU-DEIVJSAASA-N
UniChem Connectivity Search for chemical match using the InChIKey ZPMXCTSMZFCELU-DEIVJSAASA-N