(7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-[4-(2H3)methylpiperazin-1-yl]carboximidoyl]-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-13-yl acetate

• ChemBase ID: 177540
• Molecular Formular: C43H58N4O12
• Molecular Mass: 822.94022
• Monoisotopic Mass: 822.40512332
• 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)OC(=O)C)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)OC(=O)C)C)O)C)O)C)/C
• InChI: InChI=1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14+,22-13-,44-20+/t21-,23-,24+,25+,29-,34-,35+,39+,43-/m0/s1
• InChIKey: JQXXHWHPUNPDRT-WQCUSGOUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-[4-(^2H₃)methylpiperazin-1-yl]carboximidoyl]-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-13-yl acetate
• IUPAC Traditional name: (7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-[4-(^2H₃)methylpiperazin-1-yl]carboximidoyl]-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-13-yl acetate
• Synonyms: Rifampin-d3; Rifaldazine-d3; Rifamycin AMP-d3; R/AMP-d3; Abrifam; -d3 Eremfat-d3; Rifa-d3; Rifampicin-d3; 3-[[(4-Methyl-d3-1-piperazin-yl)imino]methyl]rifamycin

Database IDs

• PubChem SID: 164233450
• PubChem CID: 71752080

CALCULATED PROPERTIES

• Acid pKa: 6.8984513
• H Acceptors: 14
• H Donor: 6
• LogD (pH = 5.5): 1.6852435
• LogD (pH = 7.4): 2.7622907
• Log P: 2.7698967
• Molar Refractivity: 225.5828 cm^3
• Polarizability: 86.47999 Å^3
• Polar Surface Area: 220.15 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dimethyl Sulfoxide; Ethyl Acetate; Methanol; Tetrahydrofuran,
• Apperance: Red Solid
• Melting Point: >155°C (dec)

Safety Information

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

DETAILS

Toronto Research Chemicals - R508002

Semisynthetic antibiotic. Antibacerial (tuberculostatic).

REFERENCES

• Furesz, et al.: Antibiot. Chemother., 16, 316 (1970)
• Gallo, G.G., et al.: Anal. Profiles Drug Subs., 5, 467 (1970)