BAL19403   Click here for help

GtoPdb Ligand ID: 10981

Synonyms: BAL 19403 | BAL-19403
Compound class: Synthetic organic
Comment: BAL19403 is an experimental macrolide antibacterial [1]. It has in vitro activity against propionibacteria, including erythromycin- and clindamycin-resistant propionibacteria, and exhibits some anti-inflammatory activity. It was proposed as a topical agent for mild to moderate inflammatory acne vulgaris.
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 16
Hydrogen bond donors 2
Rotatable bonds 12
Topological polar surface area 224.76
Molecular weight 948.51
XLogP 3.87
No. Lipinski's rules broken 2

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 CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@@H]([C@](C2)(C)OC)O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C[C@H](C(=O)[C@@H]([C@@H]2[C@]1(C)OC(=O)[C@H]2SCCn1cnc2c1nccc2)C)C)(C)OC
Isomeric SMILES CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@@H]([C@](C2)(C)OC)O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C[C@H](C(=O)[C@@H]([C@@H]2[C@]1(C)OC(=O)[C@H]2SCCn1cnc2c1nccc2)C)C)(C)OC
InChI InChI=1S/C48H76N4O13S/c1-15-33-48(10)35(39(44(57)65-48)66-20-19-52-24-50-31-17-16-18-49-42(31)52)27(4)36(53)25(2)22-47(9,59-14)41(64-45-37(54)32(51(11)12)21-26(3)60-45)28(5)38(29(6)43(56)62-33)63-34-23-46(8,58-13)40(55)30(7)61-34/h16-18,24-30,32-35,37-41,45,54-55H,15,19-23H2,1-14H3/t25-,26-,27-,28+,29-,30+,32+,33-,34+,35+,37-,38+,39+,40+,41-,45+,46-,47-,48-/m1/s1
InChI Key HTEVRIKKCSOLOA-AKGQNOEZSA-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 Synthetic organic
IUPAC Name Click here for help
(1S,2R,5R,6S,7S,8R,9R,11R,13R,14R,15S)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-6-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-15-(2-imidazo[4,5-b]pyridin-3-ylethylsulfanyl)-9-methoxy-1,5,7,9,11,13-hexamethyl-3,17-dioxabicyclo[12.3.0]heptadecane-4,12,16-trione
Synonyms Click here for help
BAL 19403 | BAL-19403
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo BAL19403
Other databases
ChEMBL Ligand CHEMBL405863
GtoPdb PubChem SID 405560422
PubChem CID 11528098
Search Google for chemical match using the InChIKey HTEVRIKKCSOLOA-AKGQNOEZSA-N
Search Google for chemicals with the same backbone HTEVRIKKCSOLOA
UniChem Compound Search for chemical match using the InChIKey HTEVRIKKCSOLOA-AKGQNOEZSA-N
UniChem Connectivity Search for chemical match using the InChIKey HTEVRIKKCSOLOA-AKGQNOEZSA-N