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Entry
CA00576                                                            

Classification
Carotenoid Name
Peridininol;
Peridinol
IUPAC name (3S,5R,6S,3'S,5'R,6'R)-5,6-Epoxy-3,3',5'-trihydroxy-6',7'-didehydro-5,6,5',6'-tetrahydro-12',13',20'-trinor-beta,beta-caroten-19,11-olide
Formula
C37H48O6
Molecular Weight 
588.754 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: CA00413, CA00577
  • InChI
    InChI=1S/C37H48O6/c1-25(15-16-31-33(3,4)21-28(38)23-35(31,7)41)13-11-9-10-12-14-26(2)19-30-20-27(32(40)42-30)17-18-37-34(5,6)22-29(39)24-36(37,8)43-37/h9-15,17-20,28-29,38-39,41H,21-24H2,1-8H3/b11-9+,12-10+,18-17+,25-13+,26-14+,30-19-/t16-,28-,29-,35+,36+,37-/m0/s1
    InChIKey
    GWNBJBMUGIZCIP-VGIKQORDSA-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)O
    XLogP
    7.509
    Hydrogen Bond donors
    (Lipinski's definition)
    3
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    6
    LipinskiFailures
    1
    Complexity of molecule
    0.341
    Number of heavy atoms
    43
    TPSA
    (Topological Polar Surface Area) 
    99.520 Å2
    Source organisms
    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
    Paphia amabilis (Ref.312) - Shellfish: bivalve, Venus amabilis
    Corbicula japonica (Ref.221) - Shellfish: bivalve
    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.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.312 : Maoka, Takashi; Akimoto, Naoshige; Yim, Mi-Jin; Hosokawa, Masashi; Miyashita, Kazuo, Journal of Agricultural and Food Chemistry (2008), 56(24), 12069-12072., "New C37 Skeletal Carotenoid from the Clam, Paphia amabillis".
  • Ref.221 : Maoka, Takashi; Fujiwara, Yasuhiro; Hashimoto, Keiji; Akimoto, Naoshige, Journal of Agricultural and Food Chemistry (2005), 53(21), 8357-8364. "Carotenoids in Three Species of Corbicula Clams, Corbicula japonica, Corbicula sandai, and Corbicula sp. (Chinese Freshwater Corbicula Clam)".
  • CAS
    54369-14-1
    Links to other DB
    KNApSAcK: C00023163

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