(7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E)-2,13,15,17,27,29-hexahydroxy-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-octaene-26-carbaldehyde

• ChemBase ID: 169375
• Molecular Formular: C36H45NO12
• Molecular Mass: 683.742
• Monoisotopic Mass: 683.29417589
• 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=O
• Canonical SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(O)c(C=O)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/C36H45NO12/c1-15-10-9-11-16(2)35(46)37-26-21(14-38)31(43)23-24(32(26)44)30(42)20(6)33-25(23)34(45)36(7,49-33)48-13-12-22(47-8)17(3)28(40)19(5)29(41)18(4)27(15)39/h9-15,17-19,22,27-29,39-44H,1-8H3,(H,37,46)/b10-9+,13-12+,16-11-/t15-,17+,18+,19-,22-,27-,28+,29+,36-/m0/s1
• InChIKey: GGZYOFVKHSKDIP-WSMWQBPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E)-2,13,15,17,27,29-hexahydroxy-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-octaene-26-carbaldehyde
• IUPAC Traditional name: (7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E)-2,13,15,17,27,29-hexahydroxy-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-octaene-26-carbaldehyde
• Synonyms: 1,2-Dihydro-5,6,9,17,19,21-hexahydroxy-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-8-carboxaldehyde; 25-O-Deacetyl-3-formylrifamycin; NSC 145635; 3-Formyl-25-desacetyl RifamycinDISCONTINUED

Database IDs

• CAS Number: 16783-97-4
• PubChem SID: 162263507
• PubChem CID: 46781649

CALCULATED PROPERTIES

• Acid pKa: 6.904702
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): 4.72901
• LogD (pH = 7.4): 4.043936
• Log P: 4.745721
• Molar Refractivity: 185.2307 cm^3
• Polarizability: 70.574715 Å^3
• Polar Surface Area: 212.31 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F699000

A metabolite of Rifampicin.

REFERENCES

• Acocella, G., et al.: Clin. Pharmacokinet., 3, 108 (1978)
• Battaglia, R., et al.: J. Antimicrob. Chemother., 26, 813 (1978)
• Mor, N., et al.: Antimicrob. Agents Chemother., 39, 2073 (1978)
• Emary, W., et al.: Drug Metab. Dispos., 26, 725 (1978)