indanomycin   Click here for help

GtoPdb Ligand ID: 10949

Synonyms: X-14547A
Compound class: Natural product or derivative
Comment: Indanomycin (X-14547A) is an ionophore antibacterial [1-2]. It is synthesised by Streptomyces antibacterialus NRRL 8167 (a soil dwelling microbe) and is active against Gram-positive bacteria in vitro.
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 4
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 79.39
Molecular weight 493.32
XLogP 6.76
No. Lipinski's rules broken 1
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 CC/C(=C\C=C\[C@@H]1C=C[C@H]2[C@H]([C@@H]1C(=O)c1[nH]ccc1)CC[C@@H]2CC)/[C@@H]1O[C@H](CC[C@@H]1C)[C@H](C(=O)O)C
Isomeric SMILES CC/C(=C\C=C\[C@@H]1C=C[C@H]2[C@H]([C@@H]1C(=O)c1[nH]ccc1)CC[C@@H]2CC)/[C@@H]1O[C@H](CC[C@@H]1C)[C@H](C(=O)O)C
InChI InChI=1S/C31H43NO4/c1-5-21-13-16-25-24(21)15-14-23(28(25)29(33)26-11-8-18-32-26)10-7-9-22(6-2)30-19(3)12-17-27(36-30)20(4)31(34)35/h7-11,14-15,18-21,23-25,27-28,30,32H,5-6,12-13,16-17H2,1-4H3,(H,34,35)/b10-7+,22-9+/t19-,20+,21-,23+,24+,25+,27+,28+,30+/m0/s1
InChI Key BAIPOTOKPGDCHA-MWBHXQFBSA-N
References
1. Liu CM, Hermann TE, Liu M, Bull DN, Palleroni NJ, Prosser BL, Westley JW, Miller PA. (1979)
X-14547A, a new ionophorous antibiotic produced by Streptomyces antibioticus NRRL 8167. Discovery, fermentation, biological properties and taxonomy of the producing culture.
J Antibiot, 32 (2): 95-9. [PMID:374324]
2. Roege KE, Kelly WL. (2009)
Biosynthetic origins of the ionophore antibiotic indanomycin.
Org Lett, 11 (2): 297-300. [PMID:19072095]