novobiocin   Click here for help

GtoPdb Ligand ID: 12021

Synonyms: Albamycin® | cardelmycin | cathomycin | PA 93 | streptonivicin
Approved drug PDB Ligand
novobiocin is an approved drug (FDA (1964))
Compound class: Natural product or derivative
Comment: Novobiocin was originally isolated from the actinomycete Streptomyces niveus and belongs to the aminocoumarins, a class of compounds characterized by a 3-amino-4,7-dihydroxycoumarin ring. It is effective against Gram-positive bacteria but has limited activity against Gram-negative pathogens.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 8
Hydrogen bond donors 5
Rotatable bonds 10
Topological polar surface area 200.01
Molecular weight 612.23
XLogP 4.49
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES CO[C@@H]1[C@@H](OC(=O)N)[C@@H](O)[C@@H](OC1(C)C)Oc1ccc2c(c1C)oc(=O)c(c2O)NC(=O)c1ccc(c(c1)CC=C(C)C)O
Isomeric SMILES Cc1c(ccc2c1oc(=O)c(c2O)NC(=O)c1cc(c(cc1)O)CC=C(C)C)O[C@H]1[C@@H]([C@@H]([C@H](C(O1)(C)C)OC)OC(=O)N)O
InChI InChI=1S/C31H36N2O11/c1-14(2)7-8-16-13-17(9-11-19(16)34)27(37)33-21-22(35)18-10-12-20(15(3)24(18)42-28(21)38)41-29-23(36)25(43-30(32)39)26(40-6)31(4,5)44-29/h7,9-13,23,25-26,29,34-36H,8H2,1-6H3,(H2,32,39)(H,33,37)/t23-,25+,26-,29-/m1/s1
InChI Key YJQPYGGHQPGBLI-KGSXXDOSSA-N
No information available.
Summary of Clinical Use Click here for help
Novobiocin was approved by the FDA in 1964 and used in the treatment of serious infections caused by susceptible strains of Staphylococcus aureus. Pfizer stopped manufacture in 1999 and FDA approval was withdrawn in 2011 for reasons of safety or effectiveness.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Novobiocin is a potent inhibitor of DNA gyrase, a type II DNA topoisomerase that catalyzes the negative supercoiling of DNA and is essential in all bacteria but absent from higher eukaryotes [3].