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Entry
CA00672                                                            

Classification
Carotenoid Name
3'-Dehydrouriolide
IUPAC name (3S,5R,6S,6'R)-5,6-Epoxy-3-hydroxy-3'-oxo-5,6,7',8'-tetrahydro-beta,epsilon-caroten-19',11'-olide
Formula
C40H52O5
Molecular Weight 
612.816 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9 and 2 including one lactone and one ketone (11 in total)
Number of
conjugated multiple bonds 
9 and 2 including one lactone and one ketone (11 in total)
Isomers 
  • Constitutional isomer: CA00510, CA00749, CA00756
  • InChI
    InChI=1S/C40H52O5/c1-27(15-12-16-28(2)19-20-40-38(7,8)25-33(42)26-39(40,9)45-40)13-10-11-14-29(3)21-34-23-31(36(43)44-34)17-18-35-30(4)22-32(41)24-37(35,5)6/h10-16,19-23,33,35,42H,17-18,24-26H2,1-9H3/b11-10+,15-12+,20-19+,27-13+,28-16+,29-14+,34-21-/t33-,35-,39+,40-/m0/s1
    InChIKey
    NGKSEVYOCARGLQ-KFNUOSPMSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C/1\C=C(C(=O)O1)CC[C@H]1C(=CC(=O)CC1(C)C)C)/C)/C=C/C=C(/C=C/[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)\C
    XLogP
    8.316
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    5
    LipinskiFailures
    1
    Complexity of molecule
    0.340
    Number of heavy atoms
    45
    TPSA
    (Topological Polar Surface Area) 
    76.130 Å2
    Source organisms
    Bathycoccus prasinos (Ref.46) - Green alga: Prasinophyte
    References
  • Ref.46 : E. S. Egeland, R. R. L. Guillard, and S. Liaaen-Jensen, Phytochemistry, Vol. 44, No. 6, pp.1087-1097, 1997, "Additional carotenoid prototype representatices and general chemosystematic evaluation of carotenoids in prasinophyceae (chlorophyta)".
  • CAS
    168781-50-8
    Links to other DB
    KNApSAcK: C00023075

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