Carotenoids obi
All carotenoids     All organisms   Feedback
Carotenoids DB          Carotenoids DB: CA00630   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible pathways   ]
Entry
CA00630                                                            

Classification
Carotenoid Name
Chrysanthemaxanthin
IUPAC name (3S,5R,8S,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   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Major pigment in avocado (Ref.493).
  • Reverses multidrug resistance by a co-treatment with flavoxanthin (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-SOOLLQOPSA-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@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
    Persea americana (Ref.202) - Land plant: avocado
    Calendula officinalis (Ref.430) - Land plant: common marigold
    References
  • Ref.202 : Gross, Jeana; Gabai, Michaela; Lifshitz, Abraham; Sklarz, Benjamin, Phytochemistry (Elsevier) (1974), 13(9), 1917-21., "Structures of some carotenoids from pulp of Persea americana".
  • Ref.430 : T. W. GOODWIN, Biochem J. 1954 Sep;58(1):90-4., "Studies in carotenogenesis. 13. The carotenoids of the flower petals of Calendula officinalis.".
  • Ref.493 : Anne-Laure Gagez, Valérie Thiery, Virginie Pasquet, Jean-Paul Cadoret, and Laurent Picot, Current Bioactive Compounds 2012, 8, 000-000, "Epoxycarotenoids and Cancer. Review".
  • CAS
    27780-11-6
    Links to other DB

       Search other references with Google Scholar