Virginiamycin M1

HCID 5459319

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Basic information

CAS: 21411-53-0
Standard SMILES: CC1=C\[C@@H](O)CC(=O)Cc2nc(co2)C(=O)N2CCC=C2C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC\C=C\1
InChIKey: DAIKHDNSXMZDCU-FQTGFAPKSA-N
Molecular formula: C28H35N3O7
Average molar mass: 525.6 g/mol
Monoisotopic mass: 525.24750046

Overview

Pristinamycin IIA is a macrolide that is (together with pristinamycin IA) a component of pristinamycin, an oral streptogramin antibiotic produced by Streptomyces pristinaespiralis. Pristinamycin exhibits bactericidal activity against Gram positive organisms including methicillin-resistant Staphylococcus aureus. It has a role as a Mycoplasma genitalium metabolite and an antibacterial drug. It is a secondary carboxamide, a tertiary carboxamide, a pyrroline, a lactam, a macrolide antibiotic, a macrolide, a secondary alcohol, a cyclic ketone, a member of 1,3-oxazoles and an enamide.

Names & identifiers

Preferred name: Virginiamycin M1
IUPAC: (10R,11R,12E,17E,19E,21S)-21-hydroxy-11,19-dimethyl-10-propan-2-yl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.03,7]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone

Names & synonyms

virginiamycin m1Streptogramin AMikamycin APristinamycin IIAVirginiamycin Factor M1VERNAMYCIN AStaphylomycin M1Antibiotic PA 114A121411-53-0Antibiotic pa 114a8W4UOL59AZPA-114A

Show more names

NSC-87432NSC-244426RP-12536CHEBI:99978,9,14,15,24,25-Hexahydro-14-hydroxy-3-isopropyl-4,12-dimethyl-3H-21,18-nitrilo-1H,22H-pyrrolo(2,1-c)(1,8,4,19)dioxadiazacyclotetracosine-1,7,16,22(4H,17H)-tetroneDTXSID30873800NSC87432Staphylomycin M

Database identifiers

CAS: 21411-53-0
PubChem CID: 5459319
DTXSID: DTXSID30873800
ChEMBL: CHEMBL1236670
ChEBI: CHEBI:9997
UNII: 8W4UOL59AZ
EC Number: 244-376-6

Properties

Computed structural propertiesFilling in

XLogP: 2.5
Topological polar surface area: 139 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 8
Rotatable bonds: 1
Heavy atoms: 38
Formal charge: 0
Complexity: 1,030

Experimental & physicochemical properties

DrugsPharmaceuticals -> Antibiotics

SolubilityPoorly soluble in water

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

Virginiamycin M1 is a macrocyclic lactone antibiotic that acts syngeristically with the structurally unrelated cyclic depsipeptides more commonly known as the virginiamycins B (ostreogrycin B or streptogramin B) and S to inhibit peptide elongation. This is achieved by blocking formation of a peptide bond between the growing peptide chain (peptidyl-tRNA) linked to the 50S ribosome and aminoacyl-tRNA. Virginiamycin M1 has proven to be highly active against Gram positive bacteria, particularly methicillin-resistant S. aureus.

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.