Carotenoids obi
All carotenoids     All organisms   Feedback
Carotenoids DB          Carotenoids DB: CA00746   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible pathways   ]
Entry
CA00746                                                            

Classification
Carotenoid Name
Capsanthin 3,6-epoxide
IUPAC name (3S,5R,6R,3'S,5'R)-3,6-Epoxy-5,3'-dihydroxy-5,6-dihydro-beta,kappa-caroten-6'-one
Formula
C40H56O4
Molecular Weight 
600.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Strong antioxidant activity - significantly inhibits O2 - generation in differentiated human promyelocytic HL-60 cells. (Ref.581).
  • Strong anti-inflammatory activity (Ref.581).
  • Number of
    conjugated double bonds 
    10 including one ketone (10 in total)
    Number of
    conjugated multiple bonds 
    10 including one ketone (10 in total)
    Isomers 
    InChI
    InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-22-35(42)38(9)26-33(41)25-36(38,5)6)15-11-12-16-30(2)18-14-20-32(4)23-24-40-37(7,8)27-34(44-40)28-39(40,10)43/h11-24,33-34,41,43H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,22-21+,24-23+,29-15+,30-16+,31-19+,32-20+/t33-,34-,38-,39+,40+/m0/s1
    InChIKey
    TWTPPPZIWNGQCQ-YNKJSWFTSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\[C@@]12O[C@H](CC1(C)C)C[C@@]2(C)O)/C)/C)/C=C/C=C(/C=C/C(=O)[C@]1(C)C[C@H](CC1(C)C)O)\C
    XLogP
    9.092
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    2
    Complexity of molecule
    0.310
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    66.760 Å2
    Source organisms

    References
  • Ref.581 : Murakami, A. Nakashima, M. Koshiba, T. Maoka, T. Nishino, H. Yano, M. Sumida, T. Kim, O.K. Koshimizu, K. Ohigashi, H., Cancer letters, 2000, 149, 115-123., “Modifying effects of carotenoids on superoxide and nitric oxide generation from stimulated leukocytes.” .
  • CAS
    103955-76-6
    Links to other DB
    KNApSAcK: C00023042
    LipidBank: VCA0048
    MassBank: CA000016

       Search other references with Google Scholar