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Entry
CA00635                                                            

Classification
Carotenoid Name
3'-Dehydrolutein;
Philosamiaxanthin;
3'-Oxolutein
IUPAC name (3R,6'R)-3-Hydroxy-beta,epsilon-caroten-3'-one
Formula
C40H54O2
Molecular Weight 
566.832 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
10 and 2 (12 in total)
Number of
conjugated multiple bonds 
10 and 2 (12 in total)
Isomers 
InChI
InChI=1S/C40H54O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,36-37,42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t36-,37+/m1/s1
InChIKey
OABQIJAIRYEICK-HRAWYTEHSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/[C@H]1C(=CC(=O)CC1(C)C)C)\C
XLogP
11.010
Hydrogen Bond donors
(Lipinski's definition)
1
Hydrogen Bond Acceptors
(Lipinski's definition)
2
LipinskiFailures
1
Complexity of molecule
0.312
Number of heavy atoms
42
TPSA
(Topological Polar Surface Area) 
37.300 Å2
Source organisms
Homo sapiens (Ref.196, Ref.211) - Human
References
  • Ref.196 : Bhosale P, Zhao da Y, Serban B, Bernstein PS., Invest Ophthalmol Vis Sci. 2007 Apr;48(4):1435-40., "Identification of 3-methoxyzeaxanthin as a novel age-related carotenoid metabolite in the human macula.".
  • Ref.211 : Frederick Khachik Paul S. Bernstein, and Donita L. Garland, Investigative Ophthalmology & Visual Science, August 1997, Vol. 38, No. 9, "Identification of lutein and zeaxanthin oxidation products in human and monkey retinas.".
  • CAS
    23984-55-6
    Links to other DB
    KNApSAcK: C00022983
    LipidBank: VCA1116
    MassBank: CA000074

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