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Entry
CA00702                                                            

Classification
Carotenoid Name
Dihydroprasinoxanthin epoxide
IUPAC name (3S,6R,3'R,4'S,5'R,6'R)-4',5'-Epoxy-3,6,3'-trihydroxy-7,8,4',5',7',8'-hexahydro-gamma,epsilon-caroten-8-one
Formula
C40H58O5
Molecular Weight 
618.864 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
8 including one ketone (8 in total)
Number of
conjugated multiple bonds 
8 including one ketone (8 in total)
Isomers 
  • Constitutional isomer: CA00355, CA00356, CA00427, CA00446, CA00447, CA00425, CA00426, CA00751
  • InChI
    InChI=1S/C40H58O5/c1-27(17-13-18-29(3)21-22-35-37(6,7)25-34(43)36-39(35,10)45-36)15-11-12-16-28(2)19-14-20-30(4)33(42)26-40(44)31(5)23-32(41)24-38(40,8)9/h11-20,32,34-36,41,43-44H,5,21-26H2,1-4,6-10H3/b12-11+,17-13+,19-14+,27-15+,28-16+,29-18+,30-20+/t32-,34-,35-,36+,39-,40+/m1/s1
    InChIKey
    TZIQGXRIFCNVHM-OWAUYRPESA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)C[C@@]1(O)C(C)(C)C[C@@H](CC1=C)O)/C)/C)/C=C/C=C(/CC[C@@H]1C(C)(C)C[C@H]([C@H]2[C@]1(C)O2)O)\C
    XLogP
    7.810
    Hydrogen Bond donors
    (Lipinski's definition)
    3
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    5
    LipinskiFailures
    2
    Complexity of molecule
    0.301
    Number of heavy atoms
    45
    TPSA
    (Topological Polar Surface Area) 
    90.290 Å2
    Source organisms
    Prasinococcus capsulatus (Ref.46) - Green alga: Prasinophyte
    References
  • Ref.46 : E. S. Egeland, R. R. L. Guillard, and S. Liaaen-Jensen, Phytochemistry, Vol. 44, No. 6, pp.1087-1097, 1997, "Additional carotenoid prototype representatices and general chemosystematic evaluation of carotenoids in prasinophyceae (chlorophyta)".
  • CAS
    101527-80-4
    Links to other DB
    KNApSAcK: C00023036

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