2,4,10,14-tetrahydroxy-7,7,12-trimethylpentacyclo[13.3.1.05,18.08,17.011,16]nonadeca-1(18),2,4,8,10,12,14,16-octaene-6,19-dione

• ChemBase ID: 179736
• Molecular Formular: C22H16O6
• Molecular Mass: 376.35884
• Monoisotopic Mass: 376.09468823
• SMILES: c12c3c(C(=O)C(c4c3c3c(C1=O)c(cc(c3c(c4)O)C)O)(C)C)c(cc2O)O
• Canonical SMILES: Oc1cc(O)c2c3c1C(=O)C(c1c3c3c(C2=O)c(O)cc(c3c(c1)O)C)(C)C
• InChI: InChI=1S/C22H16O6/c1-7-4-9(23)15-18-13(7)10(24)5-8-14(18)19-16(20(15)27)11(25)6-12(26)17(19)21(28)22(8,2)3/h4-6,23-26H,1-3H3
• InChIKey: ABLACSIRCKEUOB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,4,10,14-tetrahydroxy-7,7,12-trimethylpentacyclo[13.3.1.0^5,^1^8.0^8,^1^7.0^1^1,^1^6]nonadeca-1(18),2,4,8,10,12,14,16-octaene-6,19-dione
• IUPAC Traditional name: 2,4,10,14-tetrahydroxy-7,7,12-trimethylpentacyclo[13.3.1.0^5,^1^8.0^8,^1^7.0^1^1,^1^6]nonadeca-1(18),2,4,8,10,12,14,16-octaene-6,19-dione
• Synonyms: Croceomycin; Geliomycin; Heliomycin; Itamycin; Antibiotic 11-98; Antibiotic A 3733A; Antibiotic X 340; Heliomycin

Database IDs

• CAS Number: 11029-70-220004-62-0
• PubChem SID: 164235646
• PubChem CID: 5282060

CALCULATED PROPERTIES

• Acid pKa: 7.605547
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 5.8595843
• LogD (pH = 7.4): 5.629381
• Log P: 5.8629575
• Molar Refractivity: 103.2689 cm^3
• Polarizability: 40.98364 Å^3
• Polar Surface Area: 115.06 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: HIV Protease Inhibitor; RNA polymerase inhibitor

Product Information

• Biological Source: Constit. of the mycelium of Streptomyces resistomycificius and other Streptomyces spp.
• Application(s): Antibiotic; Anti-HIV; Shows activity against gram-positive and mycobacteria

REFERENCES

• Brockmann, A. et al., Chem. Ber., 1954, 87, 1036, (isol)
• Rosenbrook, W., J.O.C., 1967, 32, 2924, (struct, uv, nmr)
• Bailey, N.A. et al., Chem. Comm., 1968, 374, (cryst struct)
• Brockmann, H. et al., Chem. Ber., 1969, 102, 1224, (struct, ir, uv, nmr)
• Eckhardt, K. et al., Tetrahedron, 1970, 26, 5875, (struct, ir, uv, nmr)
• Kingston, J.F. et al., Can. J. Chem., 1977, 55, 785, (synth)
• Keay, B.A. et al., J.A.C.S., 1982, 104, 4725, (synth)
• Hfle, G. et al., Annalen, 1983, 835, (isol, biosynth, cmr)
• Kelly, T.R. et al., J.A.C.S., 1985, 107, 3879, (synth)
• Arora, S.K., J. Antibiot., 1985, 38, 113, (struct)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, HAL000