pristinamycin IA   Click here for help

GtoPdb Ligand ID: 12934

Synonyms: mikamycin B | ostreogrycin B | Pyostacine® | streptogramin B | virginiamycin B
Approved drug
pristinamycin IA is an approved drug (France, 1995)
Compound class: Natural product or derivative
Comment: Pristinamycin IA is a cyclic depsipeptide that is, together with pristinamycin IIA, a component of pristinamycin (PubChem CID 11979535), a streptogramin antibacterial produced by Streptomyces pristinaespiralis [1]. Note that the INN describes the mixture.
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 18
Hydrogen bond donors 4
Rotatable bonds 8
Topological polar surface area 227.43
Molecular weight 866.96
XLogP 0.9
No. Lipinski's rules broken 2
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@@H]1C(=O)N2CCC[C@H]2C(=O)N(C)[C@@H](CC3=CC=C(C=C3)N(C)C)C(=O)N4CCC(=O)C[C@H]4C(=O)N[C@@H](C5=CC=CC=C5)C(=O)O[C@H](C)[C@@H](C(=O)N1)NC(=O)C6=NC=CC=C6O
Isomeric SMILES CC[C@@H]1C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)N3CCC(=O)C[C@H]3C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CC6=CC=C(C=C6)N(C)C)C
InChI InChI=1S/C45H54N8O10/c1-6-31-42(59)52-22-11-14-32(52)43(60)51(5)34(24-27-16-18-29(19-17-27)50(3)4)44(61)53-23-20-30(54)25-33(53)39(56)49-37(28-12-8-7-9-13-28)45(62)63-26(2)36(40(57)47-31)48-41(58)38-35(55)15-10-21-46-38/h7-10,12-13,15-19,21,26,31-34,36-37,55H,6,11,14,20,22-25H2,1-5H3,(H,47,57)(H,48,58)(H,49,56)/t26-,31-,32+,33+,34+,36+,37+/m1/s1
InChI Key YGXCETJZBDTKRY-DZCVGBHJSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (France, 1995)
IUPAC Name Click here for help
N-[(3S,6S,12R,15S,16R,19S,22S)-3-[[4-(dimethylamino)phenyl]methyl]-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentazatricyclo[20.4.0.06,10]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
1258 pristinamycin
Synonyms Click here for help
mikamycin B | ostreogrycin B | Pyostacine® | streptogramin B | virginiamycin B
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Pristinamycin
Other databases
CAS Registry No. 3131-03-1 (source: Scifinder)
ChEBI CHEBI:8417
ChEMBL Ligand CHEMBL1256399
GtoPdb PubChem SID 485206055
PubChem CID 11136668
Search Google for chemical match using the InChIKey YGXCETJZBDTKRY-DZCVGBHJSA-N
Search Google for chemicals with the same backbone YGXCETJZBDTKRY
Search PubMed clinical trials pristinamycin
Search PubMed titles pristinamycin
Search PubMed titles/abstracts pristinamycin
UniChem Compound Search for chemical match using the InChIKey YGXCETJZBDTKRY-DZCVGBHJSA-N
UniChem Connectivity Search for chemical match using the InChIKey YGXCETJZBDTKRY-DZCVGBHJSA-N