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Entry
CA00624                                                            

Classification
Carotenoid Name
Flavoxanthin;
Chrysanthemaxanthin
IUPAC name (3S,5R,8RS,3'R,6'R)-5,8-Epoxy-5,8-dihydro-beta,epsilon-carotene-3,3'-diol
Formula
C40H56O3
Molecular Weight 
584.848 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Orange color of calendula petals (Ref.493).
  • Reverses multidrug resistance by a co-treatment with chrysanthemaxanthin (Ref.493).
  • Number of
    conjugated double bonds 
    8
    Number of
    conjugated multiple bonds 
    8
    Isomers 
    InChI
    InChI=1S/C40H56O3/c1-28(17-13-18-30(3)21-22-35-32(5)23-33(41)25-38(35,6)7)15-11-12-16-29(2)19-14-20-31(4)36-24-37-39(8,9)26-34(42)27-40(37,10)43-36/h11-24,33-36,41-42H,25-27H2,1-10H3/b12-11+,17-13+,19-14+,22-21+,28-15+,29-16+,30-18+,31-20+/t33-,34-,35-,36?,40+/m0/s1
    InChIKey
    JRHJXXLCNATYLS-FXXITGBASA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C1C=C2[C@@](O1)(C)C[C@H](CC2(C)C)O)/C)/C)/C=C/C=C(/C=C/[C@H]1C(=C[C@@H](CC1(C)C)O)C)\C
    XLogP
    9.229
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    1
    Complexity of molecule
    0.313
    Number of heavy atoms
    43
    TPSA
    (Topological Polar Surface Area) 
    49.690 Å2
    Source organisms
    Helvella pezizoides (Ref.115) - Fungi: mushroom
    Helvella esculenta (Ref.115) - Fungi: mushroom
    References
  • Ref.115 : Czeczuga, B., Phyton (Horn, Austria) (1979), 19(3-4), 225-32., "Investigations on carotenoids in fungi. VI. Representatives of the Helvellaceae and Morchellaceae".
  • Ref.493 : Anne-Laure Gagez, ValĂ©rie Thiery, Virginie Pasquet, Jean-Paul Cadoret, and Laurent Picot, Current Bioactive Compounds 2012, 8, 000-000, "Epoxycarotenoids and Cancer. Review".
  • CAS
    512-29-8
    Links to other DB
    KEGG COMPOUND: C08594
    KNApSAcK: C00003772

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