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clorobiocin   Click here for help

GtoPdb Ligand ID: 12127

Synonyms: chlorobiocin | RP 18,631
PDB Ligand
Compound class: Natural product
Comment: Clorobiocin was originally isolated from the actinomycete Streptomyces roseochromogenes and belongs to the aminocoumarins.

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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 7
Hydrogen bond donors 5
Rotatable bonds 11
Topological polar surface area 189.78
Molecular weight 696.21
XLogP 6.53
No. Lipinski's rules broken 1

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)c2ccc([nH]2)C)[C@@H](O)[C@@H](OC1(C)C)Oc1ccc2c(c1Cl)oc(=O)c(c2O)NC(=O)c1ccc(c(c1)CC=C(C)C)O
Isomeric SMILES Cc1ccc([nH]1)C(=O)O[C@H]1[C@H]([C@@H](OC([C@@H]1OC)(C)C)Oc1c(c2c(cc1)c(c(c(=O)o2)NC(=O)c1cc(c(cc1)O)CC=C(C)C)O)Cl)O
InChI InChI=1S/C35H37ClN2O11/c1-16(2)7-9-18-15-19(10-13-22(18)39)31(42)38-25-26(40)20-11-14-23(24(36)28(20)47-33(25)44)46-34-27(41)29(30(45-6)35(4,5)49-34)48-32(43)21-12-8-17(3)37-21/h7-8,10-15,27,29-30,34,37,39-41H,9H2,1-6H3,(H,38,42)/t27-,29+,30-,34-/m1/s1
InChI Key FJAQNRBDVKIIKK-LFLQOBSNSA-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
[(3R,4S,5R,6S)-6-[8-chloro-4-hydroxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-2-oxochromen-7-yl]oxy-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate
Synonyms Click here for help
chlorobiocin | RP 18,631
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Chlorobiocin (NSC 227186 in NCI compound library)
Other databases
CAS Registry No. 39868-96-7 (source: Scifinder)
ChEMBL Ligand CHEMBL303984
DrugBank Ligand DB03966
GtoPdb PubChem SID 472319249
PubChem CID 54706138
RCSB PDB Ligand CBN
Search Google for chemical match using the InChIKey FJAQNRBDVKIIKK-LFLQOBSNSA-N
Search Google for chemicals with the same backbone FJAQNRBDVKIIKK
UniChem Compound Search for chemical match using the InChIKey FJAQNRBDVKIIKK-LFLQOBSNSA-N
UniChem Connectivity Search for chemical match using the InChIKey FJAQNRBDVKIIKK-LFLQOBSNSA-N

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MedChemExpress
Clorobiocin (links to external site)
Cat. No. HY-123515