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Entry
CA00397                                                            
Classification
Carotenoid Name
Mutatochrome;
Citraxanthin;
Flavacin
IUPAC name 5,8-Epoxy-5,8-dihydro-beta,beta-carotene
Formula
C40H56O
Molecular Weight 
552.848 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Anticarcinogenic activity - moderate MDR inhibition in MCF-7 cell (Ref.493).
  • Lemon yellow color. (Ref.430).
    • Number of
    conjugated double bonds 
    9
    Number of
    conjugated multiple bonds 
    9
    Isomers 
    InChI

    InChIKey

    Canonical SMILES

    XLogP
    11.836
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    1
    Complexity of molecule
    0.320
    Number of heavy atoms
    41
    TPSA
    (Topological Polar Surface Area) 
    9.230 Å2
    Reaction
  • Product: CR00162
    • Pathway
    Major carotenoid information

    Minor carotenoid information

    Source organisms
    Oscillatoria agardhii (Ref.1) - Cyanobacteria: other name is Planktothrix agardhii (Cyanobacteria - Microcoleaceae)
    Aphanizomenon flos-aquae (Ref.1) - Cyanobacteria (Cyanobacteria - Aphanizomenonaceae)
    Phormidium foveolarum (Ref.1) - Cyanobacteria (Cyanobacteria - Oscillatoriaceae)
    Phormidium percicinum (Ref.1) - Cyanobacteria (Cyanobacteria - Oscillatoriaceae)
    Chlamydomonas reinhardtii (Ref.12, Ref.13, Ref.14) - Green alga: Chlamydomonadales, unicellular green alga (Chlorophyta - Chlamydomonadaceae)
    Solanum lycopersicum (Ref.346) - Land plant: Solanaceae: tomato, same as Lycopersicon esculentum (Streptophyta - Solanaceae)
    Citrus sinensis L. Osbeck (Ref.373) - Land plant: orange (Streptophyta - Rutaceae)
    Calendula officinalis (Ref.430) - Land plant: common marigold (Streptophyta - Asteraceae)
    References
  • Ref.1: S. Hertzberg, S. Liaaen-Jensen, and H. W. Siegelman, Phytochemistry, 1971, Vol. 10, pp. 3121 - 3127 "The carotenois of blue-green algae".
  • Ref.12: N.I. Krinsky and R. P. Levine, Plant Physiol. Jul 1964; 39(4): 680–687. "Carotenoids of Wild Type and Mutant Strains of the Green Alga, Chlamydomonas reinhardi".
  • Ref.13: PMID: 1190948: Francis GW, Strand LP, Lien T, Knutsen G., Arch Microbiol. 1975 Aug 28;104(3):249-54. "Variations in the Carotenoid Content of Chlamydomonas reinhardii throughout the Cell cycle".
  • Ref.14: S. Tkaichi, and M. Mimuro, Plant Cell Physiol. 39(9): 968-977 (1998) "Distribution and Geometric Isomerism of Neoxanthin in Oxygenic Phototrophs: 9'-Cis, a Sole Molecular Form".
  • Ref.346: Avraham Ben-Aziz, George Britton, Trevor W. Goodwin, Phytochemistry, Volume 12, Issue 11, November 1973, Pages 2759-2764, "Carotene epoxides of Lycopersicon esculentum".
  • Ref.373: Kudritskaya, S. E.; Fishman, G. M.; Zagorodskaya, L. M., Subtropicheskie Kul'tury (1977), (5-6), 154-8., "Identification of orange peel (Citrus sinensis Osb.) carotenoids".
  • 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
    515-06-0
    Links to other DB
    KNApSAcK: C00003779

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