N-[(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-pentaazatricyclo[20.4.0.06,10]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide

• ChemBase ID: 176922
• Molecular Formular: C45H54N8O10
• Molecular Mass: 866.95786
• Monoisotopic Mass: 866.39628997
• SMILES: c1cc(ccc1N(C)C)CC1N(C(=O)[C@H]2N(C(=O)[C@@H](NC(=O)[C@H]([C@H](OC(=O)[C@@H](NC(=O)[C@H]3N(C1=O)CCC(=O)C3)c1ccccc1)C)NC(=O)c1ncccc1O)CC)CCC2)C
• Canonical SMILES: CC[C@@H]1NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)C(N(C(=O)[C@H]3N(C1=O)CCC3)C)Cc1ccc(cc1)N(C)C)CCC(=O)C2)c1ccccc1
• 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
• InChIKey: YGXCETJZBDTKRY-FULBRLTBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(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-pentaazatricyclo[20.4.0.0^6,^1^0]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
• IUPAC Traditional name: N-[(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-pentaazatricyclo[20.4.0.0^6,^1^0]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
• Synonyms: 4-[4-(Dimethylamino)-N-methyl-L-phenylalanine]virginiamycin S1; Ostreogrycin B; Antibiotic PA 114B; Antibiotic PA 114B1; Mikamycin B; Mikamycin IA; N-[(3-Hydroxy-2-pyridinyl)carbonyl]-L-threonyl-(2R)-2-aminobutanoyl-L-prolyl-4-(dimethylamino)-N-methyl-L-phenylalanyl-(2S)-4-oxo-2-piperidinecarbonyl-(2S)-2-phenylglycine (6-13)-lactone; NSC 92554; PA 114B; Pristinamycin P 1; Streptogramin B; Vernamycin Bα; Pristinamycin IADISCONTINUED

Database IDs

• CAS Number: 3131-03-1
• PubChem SID: 164232832
• PubChem CID: 71751769

CALCULATED PROPERTIES

• Acid pKa: 7.532488
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): 1.8564891
• LogD (pH = 7.4): 1.7259781
• Log P: 1.9611944
• Molar Refractivity: 227.6658 cm^3
• Polarizability: 87.76497 Å^3
• Polar Surface Area: 227.96 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P745000

One of the two major components of Pristinamycin (Pristinamycin IA and Pristinamycin IIA (or Virginiamycin M1-V673810).

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)