(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-26-formyl-2,15,17,27,29-pentahydroxy-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-13-yl acetate

• ChemBase ID: 169431
• Molecular Formular: C38H47NO13
• Molecular Mass: 725.77868
• Monoisotopic Mass: 725.30474057
• 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=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)OC(=O)C)C)O)C)O)C)/C
• InChI: InChI=1S/C38H47NO13/c1-16-11-10-12-17(2)37(48)39-28-23(15-40)32(45)25-26(33(28)46)31(44)21(6)35-27(25)36(47)38(8,52-35)50-14-13-24(49-9)18(3)34(51-22(7)41)20(5)30(43)19(4)29(16)42/h10-16,18-20,24,29-30,34,42-46H,1-9H3,(H,39,48)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,24-,29-,30+,34+,38-/m0/s1
• InChIKey: BBNQHOMJRFAQBN-UPZFVJMDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-26-formyl-2,15,17,27,29-pentahydroxy-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-13-yl acetate
• IUPAC Traditional name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-26-formyl-2,15,17,27,29-pentahydroxy-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-13-yl acetate
• 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 21-Acetate; 3-Formylrifampicin SV; NCI 145-635; Rifaldehyde; 3-Formyl Rifamycin

Database IDs

• CAS Number: 13292-22-3
• PubChem SID: 162263563
• PubChem CID: 12888670

CALCULATED PROPERTIES

• Acid pKa: 6.904702
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): 5.1701355
• LogD (pH = 7.4): 4.4850616
• Log P: 5.1868463
• Molar Refractivity: 194.3822 cm^3
• Polarizability: 74.42235 Å^3
• Polar Surface Area: 218.38 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Black-Red Solid
• Melting Point: >122°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - F700950

A metabolite of Rifampicin, a Rifamycin antibiotic.

REFERENCES

• Assandri, A., et al.: J. Antibiot., 37, 1066 (1984)
• Utkin, I., et al.: Drug. Metab. Dispos., 25, 963 (1984)
• Weber, A., et al.: Biopharm. Drug. Dispos., 22(1984)
• 157 (1984)
• Marek, C., et al.: Biochem. J., 387, 601 (1984)