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Entry
CA00441                                                            

Classification
Carotenoid Name
(8'R)-Luteoxanthin
IUPAC name (3S,5R,6S,3'S,5'R,8'R)-5,6:5',8'-Diepoxy-5,6,5',8'-tetrahydro-beta,beta-carotene-3,3'-diol
Formula
C40H56O4
Molecular Weight 
600.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Reverse MDR in MCF-7 cells and potentiate epirubicin antiproliferative activity in L5178 (Ref.492).
  • Number of
    conjugated double bonds 
    8
    Number of
    conjugated multiple bonds 
    8
    Isomers 
    InChI
    InChI=1S/C40H56O4/c1-28(17-13-18-30(3)21-22-40-37(7,8)25-33(42)27-39(40,10)44-40)15-11-12-16-29(2)19-14-20-31(4)34-23-35-36(5,6)24-32(41)26-38(35,9)43-34/h11-23,32-34,41-42H,24-27H2,1-10H3/b12-11+,17-13+,19-14+,22-21+,28-15+,29-16+,30-18+,31-20+/t32-,33-,34+,38+,39+,40-/m0/s1
    InChIKey
    YNNRPBRNWWIQPQ-JUINZOCDSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\[C@H]1C=C2[C@@](O1)(C)C[C@H](CC2(C)C)O)/C)/C)/C=C/C=C(/C=C/[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)\C
    XLogP
    7.710
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    1
    Complexity of molecule
    0.320
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    62.220 Å2
    Source organisms
    Rosa foetida (Ref.285) - Land plant: Rosaceae: rose petal
    References
  • Ref.285 : Edith Märki-Fischer, Richard Buchecker, and Conrad Hans Eugster, Helvetica Chimica Acta Volume 67, Issue 8, pages 2143–2154, 19 Dezember 1984, "Eine Neuuntersuchung der Carotinoide aus Rosa foetida: Struktur von 12 neuen Carotinoiden; stereoisomere Luteoxanthine, Auroxanthine, Latoxanthine und Latochrome".
  • Ref.492 : Péter Molnár, József Deli, Toru Tanaka,Yoshiyuki Kann, Satoru Tani, Nóra Gyémánt, Joseph Molnár ,and Masami Kawase, Phytotherapy Research, Volume 24, Issue 5, pages 644–648, May 2010, “Carotenoids with anti-Helicobacter pylori activity from Golden deliciousapple”.
  • CAS
    95119-74-7
    Links to other DB

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