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Entry
CA00715                                                            

Classification
Carotenoid Name
Sioxanthin
IUPAC name (2'S)-1'-(beta-D-Glucopyranosyloxy)-3',4'-didehydro-1',2'-dihydro-phi,psi-caroten-2'-ol
Formula
C46H62O7
Molecular Weight 
726.956 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
14
Number of
conjugated multiple bonds 
14
Isomers 
  • Constitutional isomer: CA00267
  • InChI
    InChI=1S/C46H62O7/c1-31(16-11-12-17-32(2)19-14-22-34(4)24-28-39-37(7)27-26-36(6)38(39)8)18-13-20-33(3)21-15-23-35(5)25-29-41(48)46(9,10)53-45-44(51)43(50)42(49)40(30-47)52-45/h11-29,40-45,47-51H,30H2,1-10H3/b12-11+,18-13+,19-14+,21-15+,28-24+,29-25+,31-16+,32-17+,33-20+,34-22+,35-23+/t40-,41+,42-,43+,44-,45+/m1/s1
    InChIKey
    UHUTZRAVSUSRQE-SXKSDAIHSA-N
    Canonical SMILES
    OC[C@H]1O[C@@H](OC([C@H](/C=C/C(=C/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/c2c(C)ccc(c2C)C)\C)\C)/C)/C)/C)O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
    XLogP
    12.840
    Hydrogen Bond donors
    (Lipinski's definition)
    5
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    7
    LipinskiFailures
    2
    Complexity of molecule
    0.322
    Number of heavy atoms
    53
    TPSA
    (Topological Polar Surface Area) 
    119.610 Å2
    Source organisms
    Salinispora tropica (Ref.156) - Actinobacteria
    References
  • Ref.156 : Taylor K. S. Richter, Chambers C. Hughes, and, Bradley S. Moore, Environ Microbiol. (2014) Oct 20. doi: 10.1111/1462-2920.12669, "Sioxanthin, a novel glycosylated carotenoid, reveals an unusual subclustered biosynthetic pathway".
  • CAS
    -
    Links to other DB
    ProCarDB: C1801

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