BC-7013   Click here for help

GtoPdb Ligand ID: 11034

Synonyms: BC7013
Compound class: Synthetic organic
Comment: BC-7013 is a pleuromutilin antibacterial. The chemical structure shown here was drawn from Tang et al. (2012) [1-2].
In 2007 retapamulin became the first pleuromutilin approved for use in humans, and lefamulin was FDA approved in 2019.
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 CDK toolkit. 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 5
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 109.13
Molecular weight 500.26
XLogP 4.89
No. Lipinski's rules broken 0
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.

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Canonical SMILES C=C[C@]1(C)C[C@@H](OC(=O)CSc2ccc(cc2)CO)[C@]2(C)C(C)CC[C@]3([C@H]([C@@H]1O)C)C2C(=O)CC3
Isomeric SMILES C=C[C@]1(C)C[C@@H](OC(=O)CSc2ccc(cc2)CO)[C@]2(C)C(C)CC[C@]3([C@H]([C@@H]1O)C)C2C(=O)CC3
InChI InChI=1S/C29H40O5S/c1-6-27(4)15-23(34-24(32)17-35-21-9-7-20(16-30)8-10-21)28(5)18(2)11-13-29(19(3)26(27)33)14-12-22(31)25(28)29/h6-10,18-19,23,25-26,30,33H,1,11-17H2,2-5H3/t18?,19-,23+,25?,26-,27+,28-,29-/m0/s1
InChI Key NOQBAJLIGCZEQP-CREOWZIVSA-N
References
1. Shang R, Wang J, Guo W, Liang J. (2013)
Efficient antibacterial agents: a review of the synthesis, biological evaluation and mechanism of pleuromutilin derivatives.
Curr Top Med Chem, 13 (24): 3013-25. [PMID:24200363]
2. Tang YZ, Liu YH, Chen JX. (2012)
Pleuromutilin and its derivatives-the lead compounds for novel antibiotics.
Mini Rev Med Chem, 12 (1): 53-61. [PMID:22070694]