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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   
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
    InChI=1S/C39H50O7/c1-26(16-17-33-35(4,5)24-32(44-28(3)40)25-37(33,8)43)14-12-10-11-13-15-27(2)20-31-21-29(34(42)45-31)18-19-39-36(6,7)22-30(41)23-38(39,9)46-39/h10-16,18-21,30,32,41,43H,22-25H2,1-9H3/b12-10+,13-11+,19-18+,26-14+,27-15+,31-20-/t17-,30-,32-,37+,38+,39-/m0/s1
    InChIKey
    UYRDHEJRPVSJFM-FROCQLDGSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C\C=C(\C=C/1\C=C(C(=O)O1)/C=C/[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)/C)/C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)OC(=O)C
    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
    Source organisms
    Gymnodinum nelsoni (Ref.33) - Alga: Dinoflagellate
    Gymnodinum splendens (Ref.33) - Alga: Dinoflagellate
    Gyrodinium dorsum (Ref.33) - Alga: Dinoflagellate
    Glenodinium sp. (Ref.33) - Alga: Dinoflagellate
    Peridinium bipes (Ref.494) - Alga: Dinoflagellate
    Tovellia sanguinea (Ref.34) - Alga: Dinoflagellate
    Amphidinium carterae (Ref.33) - Alga: Dinoflagellate
    Amphidinium carterae (Ref.33) - Alga: Dinoflagellate
    Gymnodinum nelsoni (Ref.33) - Alga: Dinoflagellate
    Gymnodinum splendens (Ref.33) - Alga: Dinoflagellate
    Gyrodinium dorsum (Ref.33) - Alga: Dinoflagellate
    Glenodinium sp. (Ref.33) - Alga: Dinoflagellate
    Sarcophyton elegans (Ref.311) - Soft coral
    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 - H arves t ing 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".
  • CAS
    33281-81-1
    Links to other DB
    KNApSAcK: C00023241
    LipidBank: VCA0005
    MassBank: CA000091

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