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Entry
CA00772                                                            

Classification
Carotenoid Name
Isorenieradicistene;
(7Z,7'Z)-Isorenieratene;
7,7'-dicis-Isorenieratene;
7,7'-dicis-φ,φ-carotene
IUPAC name (7Z,7'Z)-phi,phi-Carotene
Formula
C40H48
Molecular Weight 
528.784 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Anticarcinogenic activity - more active than trans-Isorenieratene (Ref.491).
  • Number of
    conjugated double bonds 
    15
    Number of
    conjugated multiple bonds 
    15
    Isomers 
  • Cis/trans isomer: CA00770, CA00771
  • InChI
    InChI=1S/C40H48/c1-29(17-13-19-31(3)21-27-39-35(7)25-23-33(5)37(39)9)15-11-12-16-30(2)18-14-20-32(4)22-28-40-36(8)26-24-34(6)38(40)10/h11-28H,1-10H3/b12-11+,17-13+,18-14+,27-21-,28-22-,29-15+,30-16+,31-19+,32-20+
    InChIKey
    ZCIHMQAPACOQHT-UVWBRGAHSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C/c1c(C)ccc(c1C)C)/C)/C)/C=C/C=C(/C=C\c1c(C)ccc(c1C)C)\C
    XLogP
    17.704
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    0
    LipinskiFailures
    1
    Complexity of molecule
    0.341
    Number of heavy atoms
    40
    TPSA
    (Topological Polar Surface Area) 
    0.000 Å2
    Source organisms
    Suberites sericeus (Ref.97) - Sea sponge
    Tethya amamensis (Ref.98) - Sea sponge
    References
  • Ref.97 : Matsuno, Takao; Maoka, Takashi; Katagiri, Kiyoshi; Komori, Tadaaki, Nippon Suisan Gakkaishi (1984), 50(6), 1071-5., "A new carotenoid, isorenieradicistene from the sea sponge, Suberites sericeus".
  • Ref.98 : Tanaka, Yoshito; Soejima, Takumi; Katayama, Teruhisa, Nippon Suisan Gakkaishi (1978), 44(11), 1283-5., "Biochemical studies of the carotenoids in porifera. Distribution of the carotenoids in porifera".
  • Ref.491 : Tsushima M, Maoka T, Katsuyama M, Kozuka M, Matsuno T, Tokuda H, Nishino H, Iwashima A., Biol Pharm Bull. 1995 Feb;18(2):227-33., PMID: 7742789, "Inhibitory effect of natural carotenoids on Epstein-Barr virus activation activity of a tumor promoter in Raji cells. A screening study for anti-tumor promoters.".
  • CAS
    92934-56-0
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