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Entry
CA00647                                                            

Classification
Carotenoid Name
Siphonaxanthin
IUPAC name (3R,3'R,6'R)-3,19,3'-Trihydroxy-7,8-dihydro-beta,epsilon-caroten-8-one
Formula
C40H56O4
Molecular Weight 
600.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Anticarcinogenic activity.
  • Anti-angiogenic activity (Ref.461).
  • Inhibitory effects on antigen-induced degranulation of mast cells (Ref.461).
  • The major carotenoid in the peripheral light­harvesting complexes (LHC) of photosystem II (PSII) in green algae (Ref.461).
  • Number of
    conjugated double bonds 
    9 including one ketone (9 in total)
    Number of
    conjugated multiple bonds 
    9 including one ketone (9 in total)
    Isomers 
    InChI
    InChI=1S/C40H56O4/c1-28(16-12-17-30(3)20-21-36-31(4)22-34(42)25-39(36,6)7)14-10-11-15-29(2)18-13-19-33(27-41)38(44)24-37-32(5)23-35(43)26-40(37,8)9/h10-22,34-36,41-43H,23-27H2,1-9H3/b11-10+,16-12+,18-13+,21-20+,28-14+,29-15+,30-17+,33-19+/t34-,35+,36?/m0/s1
    InChIKey
    SUCKEYMKNGZJHK-KRGWWXKFSA-N
    Canonical SMILES
    OC/C(=C\C=C\C(=C\C=C\C=C(\C=C\C=C(\C=C\C1C(=C[C@@H](CC1(C)C)O)C)/C)/C)\C)/C(=O)CC1=C(C)C[C@H](CC1(C)C)O
    XLogP
    8.174
    Hydrogen Bond donors
    (Lipinski's definition)
    3
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    2
    Complexity of molecule
    0.300
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    77.760 Å2
    Source organisms
    Chlamydomonas parkeae (Ref.15) - Green alga: Chlamydomonadales, unicellular marine flagellate
    Microdictyon boergesenii (Ref.24) - Green alga: Ulvophyceae
    Cladophora coelothrix (Ref.24) - Green alga: Ulvophyceae
    References
  • Ref.15 : T. Sasa, S. Suda, M. M. Watanabe, S. Takaichi, Plant Cell Physiol. 33(5): 527-534(1992) "A novel carotenoid ester, Loroxanthin dodecenoate, from Pyramimonas parkeae (Prasinophyceae) and Chlorarachniophycean alga".
  • Ref.24 : Y. Yoshii, I,. Wakana, K. Miriya, S. Arai, K. Ueda, and I. Inouye, J. Phycol. 40, 1170-1177 (2004) "Carotenoid comositions of Cladophora Balls (Aegagropila linnaei) and some members of the Cladophorales (Ulvophyceae, Chlorophyta): their taxonomic and evolutionary implication".
  • Ref.461 : Tatsuya Sugawara, Ponesakki Ganesan, Zhuosi Li, Yuki Manabe, and Takashi Hirata, Mar. Drugs 2014, 12(6), 3660-3668; doi:10.3390/md12063660, "Siphonaxanthin, a Green Algal Carotenoid, as a Novel Functional Compound".
  • CAS
    28526-44-5
    Links to other DB
    KNApSAcK: C00023022
    LipidBank: VCA1076

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