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Entry
CA00741                                                            

Classification
Carotenoid Name
Mytiloxanthin
IUPAC name (3R,3'S,5'R)-3,3',8'-Trihydroxy-7,8,-didehydro-beta,kappa-caroten-6'-one
Formula
C40H54O4
Molecular Weight 
598.832 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Red color (Ref.589).
  • UV-VIS: 294 and 469 nm (Ref.589).
  • Number of
    conjugated double bonds 
    9 including one ketone (9 in total)
    Number of
    conjugated multiple bonds 
    11 including one ketone (11 in total)
    Isomers 
    InChI
    InChI=1S/C40H54O4/c1-28(17-13-18-30(3)21-22-35-32(5)23-33(41)25-38(35,6)7)15-11-12-16-29(2)19-14-20-31(4)36(43)24-37(44)40(10)27-34(42)26-39(40,8)9/h11-20,24,33-34,41-43H,23,25-27H2,1-10H3/b12-11+,17-13+,19-14+,28-15+,29-16+,30-18+,31-20+,36-24-/t33-,34+,40+/m1/s1
    InChIKey
    WSLGBPCJDUQFND-BBPSKTQQSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C(=C\C(=O)[C@]1(C)C[C@H](CC1(C)C)O)\O)/C)/C)/C=C/C=C(/C#CC1=C(C)C[C@H](CC1(C)C)O)\C
    XLogP
    9.144
    Hydrogen Bond donors
    (Lipinski's definition)
    3
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    1
    Complexity of molecule
    0.306
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    77.760 Å2
    Source organisms
    Mytilus edulis (Ref.259) - Shellfish: bivalve
    Mytilus coruscus (Ref.589) - Shellfish: bivalve
    Fusinus perplexus (Ref.442); - 
    References
  • Ref.259 : A. Khare, G.P. Moss, B.C.L. Weedon, Tetrahedron Letters Volume 14, Issue 40, 1973, Pages 3921-3924, "Mytiloxanthin and isomytiloxanthin, two novel acetylenic carotenoids".
  • Ref.589 : Takashi MAOKA and Yasuhiro FUJIWARA, J. Jpn. Oil Chem. Soc. Vol. 45, No. 7 (1996), "Absolute Configurations of Mytiloxanthin and 9-E-Mytiloxanthin" .
  • Ref.442 : Kiyoshi Katagiri, Takashi Maoka, Takao Matsuno, COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY. B, COMPARATIVE BIOCHEMISTRY, 84(4):473-476 ยท JANUARY 1986, "Carotenoids of shell fishes-VIII. Comparative biochemical studies of carotenoids in three species of spindleshell, Fusinus perplexus, F.p. ferrugineus and F. forceps".
  • CAS
    50906-61-1
    Links to other DB
    KNApSAcK: C00023023
    LipidBank: VCA0008
    MassBank: CA000080

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