2-{[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-13-(acetyloxy)-2,15,17,29-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-27-yl]oxy}acetic acid

• ChemBase ID: 177543
• Molecular Formular: C39H49NO14
• Molecular Mass: 755.80466
• Monoisotopic Mass: 755.31530525
• SMILES: c1c2c(c3c(c1OCC(=O)O)c1c(c(c3O)C)O[C@@](C1=O)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]([C@H](/C=C/C=C(\C(=O)N2)/C)C)O)C)O)C)OC(=O)C)C)OC)C)O
• Canonical SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(OCC(=O)O)cc(c(c2c(c3C)O)O)NC(=O)/C(=C\C=C\[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]1C)OC(=O)C)C)O)C)O)C)/C
• InChI: InChI=1S/C39H49NO14/c1-17-11-10-12-18(2)38(49)40-24-15-26(51-16-27(42)43)28-29(34(24)47)33(46)22(6)36-30(28)37(48)39(8,54-36)52-14-13-25(50-9)19(3)35(53-23(7)41)21(5)32(45)20(4)31(17)44/h10-15,17,19-21,25,31-32,35,44-47H,16H2,1-9H3,(H,40,49)(H,42,43)/b11-10+,14-13+,18-12-/t17-,19+,20+,21+,25-,31-,32+,35+,39-/m0/s1
• InChIKey: SQTCRTQCPJICLD-KTQDUKAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-13-(acetyloxy)-2,15,17,29-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1(29),2,4,9,19,21,25,27-octaen-27-yl]oxy}acetic acid
• IUPAC Traditional name: {[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-13-(acetyloxy)-2,15,17,29-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1(29),2,4,9,19,21,25,27-octaen-27-yl]oxy}acetic acid
• Synonyms: 4-O-(Carboxymethyl)rifamycin; [(1,2-Dihydro-5,6,17,19,21-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-9-yl)oxy]acetic Acid 21-Acetate; Rifamycin B

Database IDs

• CAS Number: 13929-35-6
• PubChem SID: 164233453
• PubChem CID: 71752081

CALCULATED PROPERTIES

• Acid pKa: 3.019189
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): 1.3423088
• LogD (pH = 7.4): -0.16319329
• Log P: 3.798221
• Molar Refractivity: 198.3651 cm^3
• Polarizability: 76.817825 Å^3
• Polar Surface Area: 227.61 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R508170

A Rifamycin (R508200) derivative as antibacterial agent.

REFERENCES

• Cellai, L., et al.: Eur. J. Med. Chem., 24, 105 (1989)
• Bartolucci, C., et al.: Pharm. Pharmacol. Lett., 3, 1 (1989)
• Lounis, N., et al.: Curr. Pharm. Des., 10, 3229 (1989)