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Entry
CA01089                                                            

Classification
Carotenoid Name
(3R,3'R,5S)-3,3',5,19'-tetrahydroxy-7',8'-didehydro-γ,ε-carotene-8-one
IUPAC name (3R,3'R,5S)-3,3',5,19'-tetrahydroxy-7',8'-didehydro-gamma,epsilon-carotene-8-one
Formula
C40H55O5
Molecular Weight 
615.84 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Anticarcinogenic activity - cytotoxic toward cultured human colon tumor cells, HCT 116 (Ref.509).
  • Number of
    conjugated double bonds 
    8 including one ketone (8 in total)
    Number of
    conjugated multiple bonds 
    10 including one ketone (10 in total)
    Isomers 
    InChI
    InChI=1S/C40H55O5/c1-28(16-12-18-30(3)36(44)23-37-39(7,8)25-34(43)26-40(37,9)45)14-10-11-15-29(2)17-13-19-32(27-41)20-21-35-31(4)22-33(42)24-38(35,5)6/h10-19,22,33-35,37,41-43,45H,9,23-27H2,1-8H3/b11-10+,16-12+,17-13+,28-14+,29-15+,30-18+,32-19-/t33-,34+,35?,37?/m0/s1
    InChIKey
    IQCZNDPXDQZDAB-YIUXEHMOSA-N
    Canonical SMILES
    OC/C(=C\C=C\C(=C\C=C\C=C(\C=C\C=C(\C(=O)CC1C(C)(C)C[C@H](C[C]1(=C)O)O)/C)/C)\C)/C#CC1C(=C[C@@H](CC1(C)C)O)C
    XLogP
    -
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    5
    LipinskiFailures
    0
    Complexity of molecule
    0.667
    Number of heavy atoms
    45
    TPSA
    (Topological Polar Surface Area) 
    17.070 Å2
    Source organisms
    Prianos osiros (Ref.509) - Sea sponge
    References
  • Ref.509 : Evan W. Rogers and Tadeusz F. Molinski, J. Nat. Prod., 2005, 68 (3), pp 450–452, DOI: 10.1021/np0497797, "A Cytotoxic Carotenoid from the Marine Sponge Prianos osiros".
  • CAS

    Links to other DB

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