(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-2,13,15,17,27,29-hexahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-[4-(2H3)methylpiperazin-1-yl]carboximidoyl]-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaene-6,23-dione

• ChemBase ID: 166127
• Molecular Formular: C41H56N4O11
• Molecular Mass: 780.90354
• Monoisotopic Mass: 780.39455863
• SMILES: c1(c2c(c3c(c1O)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)O)C)OC)C)O)/C=N/N1CCN(CC1)C
• Canonical SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(O)c(/C=N/N4CCN(CC4)C)c(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)O)C)O)C)O)C)/C
• InChI: InChI=1S/C41H56N4O11/c1-20-11-10-12-21(2)40(53)43-31-26(19-42-45-16-14-44(8)15-17-45)36(50)28-29(37(31)51)35(49)25(6)38-30(28)39(52)41(7,56-38)55-18-13-27(54-9)22(3)33(47)24(5)34(48)23(4)32(20)46/h10-13,18-20,22-24,27,32-34,46-51H,14-17H2,1-9H3,(H,43,53)/b11-10+,18-13+,21-12-,42-19+/t20-,22-,23+,24-,27-,32-,33+,34+,41-/m0/s1
• InChIKey: KUJZTIJOBQNKDR-QFNKVYEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-2,13,15,17,27,29-hexahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-[4-(^2H₃)methylpiperazin-1-yl]carboximidoyl]-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-octaene-6,23-dione
• IUPAC Traditional name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-2,13,15,17,27,29-hexahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-[4-(^2H₃)methylpiperazin-1-yl]carboximidoyl]-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-octaene-6,23-dione
• Synonyms: Desacetylrifampin-d3; 25-Desacetyl Rifampicin-d3; 25-O-Deacetyl-3-[(E)-[(4-(methyl-d3)-1-piperazinyl)imino]methyl]rifamycin; 25-Deacetylrifampicin-d3; 25-Desacetylrifampin-d3; 25-O-Deacetylrifampicin-d3; 25-O-Desacetylrifampin-d3; Deacetylrifampicin-d3; Deacetylrifampin-d3; Desacetylrifampicin-d3

Database IDs

• PubChem SID: 162260260
• PubChem CID: 71315576

CALCULATED PROPERTIES

• Acid pKa: 6.8984513
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): 1.2441181
• LogD (pH = 7.4): 2.3211653
• Log P: 2.3287714
• Molar Refractivity: 216.4313 cm^3
• Polarizability: 82.636696 Å^3
• Polar Surface Area: 214.08 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Reddish Orange Solid
• Melting Point: >162°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D288727

A labelled metabolite of Rifampicin.

REFERENCES

• Blumenfeld,O.O., et al.: J. Biol. Chem., 236, 2472 (1961)
• Cowxan, R.A., et al.: Biochem. Biophys. Res. Commun, 23, 799 (1966)