(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

• ChemBase ID: 155324
• Molecular Formular: C28H35N3O7
• Molecular Mass: 525.5934
• Monoisotopic Mass: 525.24750048
• SMILES: C[C@@H]1/C=C/C(=O)NC/C=C/C(=C/[C@H](CC(=O)Cc2nc(co2)C(=O)N2CCC=C2C(=O)O[C@H]1C(C)C)O)/C
• Canonical SMILES: O=C1NC/C=C/C(=C/[C@@H](O)CC(=O)Cc2nc(C(=O)N3C(=CCC3)C(=O)O[C@H]([C@@H](/C=C/1)C)C(C)C)co2)/C
• InChI: InChI=1S/C28H35N3O7/c1-17(2)26-19(4)9-10-24(34)29-11-5-7-18(3)13-20(32)14-21(33)15-25-30-22(16-37-25)27(35)31-12-6-8-23(31)28(36)38-26/h5,7-10,13,16-17,19-20,26,32H,6,11-12,14-15H2,1-4H3,(H,29,34)/t19-,20-,26-/m1/s1
• InChIKey: DAIKHDNSXMZDCU-XMERXJNXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10R,11R,12E,17E,19E,21S)-21-hydroxy-11,19-dimethyl-10-(propan-2-yl)-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^3,^7]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone; (10R,11R,21S)-21-hydroxy-11,19-dimethyl-10-(propan-2-yl)-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^3,^7]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone
• IUPAC Traditional name: (10R,11R,12E,17E,19E,21S)-21-hydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^3,^7]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone; (10R,11R,21S)-21-hydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^3,^7]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone
• Synonyms: (3R,4R,5E,10E,12E,14S)-8,9,14,15,24,25-Hexahydro-14-hydroxy-4,12-dimethyl-3-(1-methylethyl)-3H-21,18-nitrilo-1H,22H-pyrrolo[2,1-c][1,8,4,19]dioxadiazacyclotetracosine-1,7,16,22(4H,17H)-tetrone; Ostreogrycin A; Antibiotic PA 114A1; Factor M; NSC 244426; PA 114A; Pristinamycin IIA; RP 12536; Staphylomycin M1; Streptogramin A; Vernamycin A; Virginiamycin M1 (90%); Virginiamycin M1-dx; Mikamycin A; Staphylomycin; Virginiamycin M1

Database IDs

• CAS Number: 21411-53-0
• EC Number: 244-376-6
• MDL Number: MFCD00869411
• PubChem SID: 24900736; 162249462
• PubChem CID: 5459319

CALCULATED PROPERTIES

• Acid pKa: 11.37594
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.3762097
• LogD (pH = 7.4): 2.3763726
• Log P: 2.376421
• Molar Refractivity: 144.1718 cm^3
• Polarizability: 53.66527 Å^3
• Polar Surface Area: 139.04 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ~95%
• Empirical Formula (Hill Notation): C28H35N3O7

DETAILS

Sigma Aldrich - V2753

Application
The antibiotic virginiamycin is produced by Streptomyces virginiae and is a member of the virginiamycin family. Each member is produced as a mixture of two structurally different compounds that exhibit synergistic antibacterial activity. There are two groups: virginiamycin M1 (VM1) and virginiamycin S (VS). VM1 is a polyunsaturated macrocyclic petolide. VM1 and VS are both used to inhibit protein synthesis since they are bacteriostatic. When used in combination they are more effective. Virginiamycin is used as a performance promoter in animal husbandry. They are chemically modified to make therapeutic drugs such as quinupristin and dalfopristin1.
Biochem/physiol Actions
Virginiamycin M1 inhibits bacterial protein synthesis at the level of aminoacyl-tRNA binding and peptide bond formation. It inactivates the 50S ribosome. S. virginiae inactivates VM1 by reducing its 16-carbonyl group, forming 16R-dihydroVM1. VM1 reductase participates solely in VM1 inactivation in vivo2.

Toronto Research Chemicals - V673812

Labelled Virginiamycin M1 (V673810). Macrolactone antibiotic. Antibacterial; growth promotant.

Toronto Research Chemicals - V673810

Macrolactone antibiotic. Antibacterial; growth promotant.

REFERENCES

• Crooy, P., et al.: J. Antibiot., 25, 371 (1972)
• Allington, D., et al.: Clin. Therap., 23, 24 (1972)
• Eeman, M., et al.: Langmuir, 22, 11337 (1972)
• Crooy, P., et al.: J. Antibiot., 25, 371 (1972)
• Allington, D., et al.: Clin. Therap., 23, 24 (1972)
• Eeman, M., et al.: Langmuir, 22, 11337 (1972)