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Entry
CA00700                                                            

Classification
Carotenoid Name
(6S,3'S,6'S)-3'-Hydroxy-ε-caroten-3-one;
(6S,3'S,6'S)-3'-Hydroxy-epsilon,epsilon-caroten-3-one
IUPAC name (6S,3'S,6'S)-3'-Hydroxy-epsilon,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 
9 and 2 including one ketone (11 in total)
Number of
conjugated multiple bonds 
9 and 2 including one ketone (11 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/h11-26,35,37-38,41H,27-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,37-,38-/m1/s1
InChIKey
OTHWKRBAHPOBSP-FDYQWYAWSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\[C@@H]1C(=CC(=O)CC1(C)C)C)/C)/C)/C=C/C=C(/C=C/[C@@H]1C(=C[C@H](CC1(C)C)O)C)\C
XLogP
11.729
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.211) - Human
Thunnus obesus (Ref.367) - Bony fish: bigeye tuna
Acanthochiton defilippii (Ref.366) - 
Acanthochiton rubrolineatus (Ref.366); - 
References
  • 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.".
  • Ref.367 : Ikuno, Yoshihiro; Matsuno, Takao, Nippon Suisan Gakkaishi (1987), 53(10), 1893-6., "Carotenoids and their metabolism in big-eye tuna Thunnus obesus".
  • Ref.366 : Tsushima, Miyuki; Maoka, Takashi; Matsuno, Takao, Comparative Biochemistry and Physiology, Part B:  Biochemistry & Molecular Biology (1989), 93B(3), 665-71., "Comparative biochemical studies of carotenoids in marine invertebrates - the first positive identification of ε,ε-carotene derivatives and isolation of two new carotenoids from chitons".
  • CAS
    97112-40-8
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