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Entry
CA00673                                                            
Classification
Carotenoid Name
Uriolide
IUPAC name (3S,5R,6S,3'R,6'R)-5,6-Epoxy-3,3'-dihydroxy-5,6,7',8'-tetrahydro-beta,epsilon-caroten-19',11'-olide
Formula
C40H54O5
Molecular Weight 
614.832 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9 including one lactone (9 in total)
Number of
conjugated multiple bonds 
9 including one lactone (9 in total)
Isomers 
  • Constitutional isomer: CA00511, CA00649, CA00750
    • InChI

    InChIKey

    Canonical SMILES

    XLogP
    8.589
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    5
    LipinskiFailures
    1
    Complexity of molecule
    0.333
    Number of heavy atoms
    45
    TPSA
    (Topological Polar Surface Area) 
    79.290 Å2
    Reaction
  • Substrate: CR00148
  • Product: CR00163
    • Pathway
  • Pathway: CB000074,  CB000075
    • Major carotenoid information
    Dominant pigment in prasinophytes (Ref.707).
    Minor carotenoid information

    Source organisms
    Bathycoccus prasinos (Ref.46) - Green alga: Prasinophyte (Chlorophyta - Bathycoccaceae)
    Mantoniella squamata (Ref.46, Ref.47) - Green alga: Prasinophyte (Chlorophyta - Mamiellaceae)
    Micromonas pusilla (Ref.46, Ref.47) - Green alga: Prasinophyte (Chlorophyta - Mamiellaceae)
    Prasinococcus capsulatus (Ref.46) - Green alga: Prasinophyte (Chlorophyta - Prasinococcales)
    Pseudoscourfieldia marina (Ref.46) - Green alga: Prasinophyte (Chlorophyta - Pycnococcaceae)
    Arousa sp. (Ref.46) - Green alga: Prasinophyte (Unclassified chlorophyta - Unclassified chlorophyta)
    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)".
  • Ref.47: E. S. Egeland, W. Eikrem, J. Throndsen, C. Wilhelm, M. Zapata, and S. Liaaen-Jensen, Biochemical systematics and Ecology, Vol. 23, NO. 7/8, pp. 747-755, 1995 "Carotenoids from Further Prasinophytes".
  • Ref.707: Suzanne Roy et al., Phytoplankton Pigments Characterization, Chemotaxonomy and Applications in Oceanography, October 2011, Cambridge University Press, pp 665-674, "Part VII - Data sheets aiding identification of phytoplankton carotenoids and chlorophylls", available at http://www.cambridge.org/gb/files/2013/6697/5826/Data_sheets_part_3_Xanthophylls.pdf, ISBN: 9781107000667.
    • CAS
    101527-89-3
    Links to other DB
    LipidBank: VCA1121

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