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Entry
CA00579                                                            
Classification
Carotenoid Name
Peridinin
IUPAC name (3S,5R,6S,3'S,5'R,6'R)-5,6-Epoxy-3'-ethanoyloxy-3,5'-dihydroxy-6',7'-didehydro-5,6,5',6'-tetrahydro-12',13',20'-trinor-beta,beta-caroten-19,11-olide
Formula
C39H50O7
Molecular Weight 
630.79 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Photosynthetic pigment (Ref.502).
  • Anticarcinogenic activity - moderate antiproliferative, moderate cytotoxicity in HeLa cell by activating caspases-8 and -9 (Ref.493, Ref.494).
    • 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: CA00428, CA01087, CA01088
    • InChI

    InChIKey

    Canonical SMILES

    XLogP
    8.249
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    7
    LipinskiFailures
    1
    Complexity of molecule
    0.323
    Number of heavy atoms
    46
    TPSA
    (Topological Polar Surface Area) 
    105.590 Å2
    Reaction
  • Substrate: CR00139,  CR00295
  • Product: CR00283
    • Pathway
  • Pathway: CB000095,  CB000096,  CB000147,  CB000148
    • Major carotenoid information
    Major carotenoid in dinoflagellates (Ref.707).
    Minor carotenoid information

    Source organisms
    Gymnodinum nelsoni (Ref.33) - Alga: Dinoflagellate ((Alveolata) - Gymnodiniaceae)
    Gymnodinum splendens (Ref.33) - Alga: Dinoflagellate ((Alveolata) - Gymnodiniaceae)
    Amphidinium carterae (Ref.33) - Alga: Dinoflagellate ((Alveolata) - Gymnodiniaceae)
    Gyrodinium dorsum (Ref.33) - Alga: Dinoflagellate ((Alveolata) - Gymnodiniaceae)
    Glenodinium sp. (Ref.33) - Alga: Dinoflagellate ((Alveolata) - Glenodiniaceae)
    Tovellia sanguinea (Ref.34) - Alga: Dinoflagellate ((Alveolata) - Tovelliaceae)
    Peridinium bipes (Ref.494) - Alga: Dinoflagellate ((Alveolata) - Peridiniaceae)
    Sarcophyton elegans (Ref.311) - Soft coral (Cnidaria - Alcyoniidae)
    References
  • Ref.33: J. E. Joansen, W. A. Svec, and S. Liaaen-Jensen, Phytochemistry, 1974, Vol.13 pp.2261-2271, "Carotenoids of the Dinophyceae".
  • Ref.494: Takashi MAOKA, Miyuki TSUSHIMA, and Hoyoku NISHINO, Chem. Pharm. Bull. 50(12) 1630—1633 (2002), "Isolation and Characterization of Dinochrome A and B, Anti-carcinogenic Active Carotenoids from the Fresh Water Red Tide Peridinium bipes".
  • Ref.34: R. Frassanito G. Flaim, I. Mancini, G. Guella, Biochemical Systematics and Ecology 34 (2006) pp.843-853, "High production of unexpected carotenoids in Dinophyceae. Astaxanthin esters from freshwater dinoflagellate Tovellia sanguinea".
  • Ref.311: Minh, Chau Van; Kiem, Phan Van; Nguyen, Hoai Nam; Nguyen, Xuan Cuong; Nguyen, Phuong Thao; Nguyen, Hai Dang; Quang, Tran Hong; Nguyen, Tien Dat; Thung, Do Cong; Thuy, Dinh Thi Thuy, Tap Chi Hoa Hoc (2010), 48(5), 627-631., "Carotenoids from the soft coral Sarcophyton elegans".
  • Ref.502: Pill-Soon Song, Prasad Koka, Barbara B. Przelin, and Francis T. Haxo, Biochemistry. 1976 Oct 5;15(20):4422-7.. PMID: 987799, "Molecular Topology of the Photosynthetic Light - Harvesting Pigment Complex, Peridinin-Chlorophyll a-Protein, from Marine Dinoflagellates".
  • 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".
  • 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
    33281-81-1
    Links to other DB
    KNApSAcK: C00023241
    LipidBank: VCA0005
    MassBank: CA000091

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