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Entry
CA01242                                                            
Classification
Carotenoid Name
Astaxanthin 5,8-epoxide;
Astaxanthin epoxide
IUPAC name 5,8-Epoxy-3,3'-dihydroxy-beta,beta-carotene-4,4'-dione
Formula
C40H52O5
Molecular Weight 
612.816 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Astaxanthin epoxides were major reaction products of astaanthin with superoxide anion radicals and hydroxyl radicals. (Ref.779)
    • 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 
  • Constitutional isomer: CA01241, CA00510, CA00672, CA00749, CA00756
    • InChI
    InChI=1S/C40H52O5/c1-26(17-13-18-28(3)21-22-31-30(5)36(43)32(41)24-38(31,6)7)15-11-12-16-27(2)19-14-20-29(4)34-23-35-39(8,9)25-33(42)37(44)40(35,10)45-34/h11-23,32-34,41-42H,24-25H2,1-10H3/b12-11+,17-13+,19-14+,22-21+,26-15+,27-16+,28-18+,29-20+
    InChIKey
    XZMFRIYEAVHLIU-FKJGWRFPSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C1C=C2C(O1)(C)C(=O)C(CC2(C)C)O)/C)/C)/C=C/C=C(/C=C/C1=C(C)C(=O)C(CC1(C)C)O)\C
    XLogP
    7.698
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    5
    LipinskiFailures
    1
    Complexity of molecule
    0.320
    Number of heavy atoms
    45
    TPSA
    (Topological Polar Surface Area) 
    83.830 Å2
    Reaction
  • Product: CR00472
    • Pathway
    Major carotenoid information
    Major reaction products of astaanthin with superoxide anion radicals and hydroxyl radicals. (Ref.779)
    Minor carotenoid information

    Source organisms
    Auto oxidation products of astaxanthin with hydroxy radicals, superoxide anion radicals, and singlet oxygen. (Ref.779) - Auto oxidation products of astaxanthin with hydroxy radicals, superoxide anion radicals, and singlet oxygen. (Unclassified non-living matter - Unclassified non-living matter)
    References
  • Ref.779: Takashi Maoka, Journal of Natural Medicines ISSN 1340-3443 Volume 74 Number 1 J Nat Med (2020) 74:1-16, “Carotenoids as natural functional pigments”, DOI 10.1007/s11418-019-01364-x.
    • CAS

    Links to other DB

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