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Entry
CA00747                                                            

Classification
Carotenoid Name
Capsochrome
IUPAC name 5,8-Epoxy-3,3'-dihydroxy-5,8-dihydro-beta,kappa-caroten-6'-one
Formula
C40H56O4
Molecular Weight 
600.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Efficiently reverse MDR activity (Ref.493).
  • Number of
    conjugated double bonds 
    9 including one ketone (9 in total)
    Number of
    conjugated multiple bonds 
    9 including one ketone (9 in total)
    Isomers 
    InChI
    InChI=1S/C40H56O4/c1-28(17-13-18-30(3)21-22-36(43)39(9)26-33(42)25-38(39,7)8)15-11-12-16-29(2)19-14-20-31(4)34-23-35-37(5,6)24-32(41)27-40(35,10)44-34/h11-23,32-34,41-42H,24-27H2,1-10H3/b12-11+,17-13+,19-14+,22-21+,28-15+,29-16+,30-18+,31-20+
    InChIKey
    WPXHAEKYWJBTNX-OMSIYMKDSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C1C=C2C(O1)(C)CC(CC2(C)C)O)/C)/C)/C=C/C=C(/C=C/C(=O)C1(C)CC(CC1(C)C)O)\C
    XLogP
    7.838
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    1
    Complexity of molecule
    0.310
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    66.760 Å2
    Source organisms
    Capsicum annuum  - Land plant: red pepper
    Protousnea sp. (Ref.388) - Fungi: lichen
    References
  • Ref.388 : B. Czeczuga, E. Czeczuga-Semeniuk, S. Calvelo, and S. Liberatore, Journal of Botanical Taxonomy and Geobotany, Volume 116, Issue 3-4, pages 195–200, August 2005, "Carotenoids in representatives of the Protousnea (Parmeliaceae), endemic genus from South America".
  • 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
    104012-89-7
    Links to other DB

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