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Entry
CA00508                                                            

Classification
Carotenoid Name
Halocynthiaxanthin
IUPAC name (3S,5R,6S,3'R)-5,6-Epoxy-3,3'-dihydroxy-7',8'-didehydro-5,6,7,8-tetrahydro-beta,beta-caroten-8-one
Formula
C40H54O4
Molecular Weight 
598.832 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Anticaricinogenic activity - significant anti-neoplastic effect (Ref.493), also induces apoptosis in colon cancer cells, breast cancer cells (Ref.584).
  • Number of
    conjugated double bonds 
    8 including one ketone (8 in total)
    Number of
    conjugated multiple bonds 
    10 including one ketone (10 in total)
    Isomers 
    InChI
    InChI=1S/C40H54O4/c1-28(17-13-18-30(3)21-22-35-32(5)23-33(41)24-37(35,6)7)15-11-12-16-29(2)19-14-20-31(4)36(43)27-40-38(8,9)25-34(42)26-39(40,10)44-40/h11-20,33-34,41-42H,23-27H2,1-10H3/b12-11+,17-13+,19-14+,28-15+,29-16+,30-18+,31-20+/t33-,34+,39-,40+/m1/s1
    InChIKey
    CNOIXMULOQWVGR-ABUIXNMTSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)C[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C#CC1=C(C)C[C@H](CC1(C)C)O)\C
    XLogP
    8.545
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    1
    Complexity of molecule
    0.316
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    70.060 Å2
    Source organisms
    Halocynthia roretzi (Ref.225) - Tunicate
    Corbicula japonica (Ref.221) - Shellfish: bivalve
    Corbicula sandai (Ref.221) - Shellfish: bivalve
    Corbicula clam (Ref.221) - Shellfish: bivalve
    References
  • Ref.225 : Takao Matsuno, Masahiro Ookubo, Tetrahedron Letters Volume 22, Issue 46, 1981, Pages 4659–4660, "A new carotenoid, halocynthiaxanthin from the sea squirt, Halocynthia roretzi".
  • 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)".
  • 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.584 : Konishi, I.; Hosokawa, M.; Sashima, T.; Kobayashi, H.; Miyashita, K., Toxicology & pharmacology, 2006, 142, 53-59., "Halocynthiaxanthin and fucoxanthinol isolated from Halocynthia roretzi induce apoptosis in human leukemia, breast and colon cancer cells. Comparative biochemistry and physiology." .
  • CAS
    81306-52-7
    Links to other DB
    KNApSAcK: C00023033
    LipidBank: VCA0004
    MassBank: CA000060

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