2-methoxy-3,5-dimethyl-6-[(2R,4Z)-4-[(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ylidene]oxolan-2-yl]-4H-pyran-4-one

• ChemBase ID: 179732
• Molecular Formular: C22H23NO6
• Molecular Mass: 397.42112
• Monoisotopic Mass: 397.15253746
• SMILES: c1(c(oc(c(c1=O)C)[C@@H]1OC/C(=C\C(=C\c2ccc([N+](=O)[O-])cc2)\C)/C1)OC)C
• Canonical SMILES: COc1oc([C@@H]2OC/C(=C\C(=C\c3ccc(cc3)[N+](=O)[O-])\C)/C2)c(c(=O)c1C)C
• InChI: InChI=1S/C22H23NO6/c1-13(9-16-5-7-18(8-6-16)23(25)26)10-17-11-19(28-12-17)21-14(2)20(24)15(3)22(27-4)29-21/h5-10,19H,11-12H2,1-4H3/b13-9+,17-10-/t19-/m1/s1
• InChIKey: GQKXCBCSVYJUMI-WACKOAQBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methoxy-3,5-dimethyl-6-[(2R,4Z)-4-[(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ylidene]oxolan-2-yl]-4H-pyran-4-one
• IUPAC Traditional name: 2-methoxy-3,5-dimethyl-6-[(2R,4Z)-4-[(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ylidene]oxolan-2-yl]-4H-pyran-4-one
• Synonyms: Distacin; Distacyne; Mycolutein; Antibiotic 74A''; Antibiotic 2814K; Antibiotic JA 2814K; Aureothin

Database IDs

• CAS Number: 2825-00-5
• PubChem SID: 164235642
• PubChem CID: 6569946

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 4.303924
• LogD (pH = 7.4): 4.303924
• Log P: 4.303924
• Molar Refractivity: 121.8705 cm^3
• Polarizability: 41.468296 Å^3
• Polar Surface Area: 90.58 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Non-competitive NADH-ubiquinone oxidoreductase (NADH dehydrogenase) inhibitor

Product Information

• Description: (R)-form
• Biological Source: Isol. from Streptomyces thioluteus, Streptomyces distallicus, Streptomyces luteoreticuli, Streptomyces netropsis and Streptoverticillium mycoheptinicum. Also from Actinomyces netropsis strain 2129
• Application(s): Antibacterial; Antifungal; Antitumour; Possesses insecticidal and pesticidal props.

REFERENCES

• Hirata, Y. et al., Tetrahedron, 1961, 14, 252, (isol, struct, uv)
• Oishi, H. et al., Agric. Biol. Chem., 1969, 33, 1990
• Cardillo, R. et al., Tetrahedron, 1974, 30, 459, (biosynth)
• Yamazaki, M. et al., Chem. Pharm. Bull., 1975, 23, 569, (isol, cmr, biosynth)
• Athunov, A.A. et al., Khim. Prir. Soedin., 1975, 11, 114; Chem. Nat. Compd. (Engl. Transl.), 1975, 11, 136, (isol, uv, pmr)
• Schwartz, J.L. et al., J. Antibiot., 1976, 29, 236
• Severinets, L.Y. et al., Antibiotiki (Moscow), 1978, 23, 7, (isol)
• Shizuri, Y. et al., Chem. Lett., 1987, 1381, (synth)
• Ishibashi, Y. et al., Tet. Lett., 1992, 33, 521, (abs config)
• Ishibashi, Y. et al., Bull. Chem. Soc. Jpn., 1995, 68, 3643, (abs config, cryst struct)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DTU200