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Entry
CA00599                                                            

Classification
Carotenoid Name
3'-Epilutein;
Lutein B;
Calthaxanthin
IUPAC name (3R,3'S,6'R)-beta,epsilon-Carotene-3,3'-diol
Formula
C40H56O2
Molecular Weight 
568.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
10
Number of
conjugated multiple bonds 
10
Isomers 
InChI
InChI=1S/C40H56O2/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/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36-,37+/m1/s1
InChIKey
KBPHJBAIARWVSC-IRHPOQNPSA-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(=C[C@H](CC1(C)C)O)C)\C
XLogP
11.283
Hydrogen Bond donors
(Lipinski's definition)
2
Hydrogen Bond Acceptors
(Lipinski's definition)
2
LipinskiFailures
1
Complexity of molecule
0.306
Number of heavy atoms
42
TPSA
(Topological Polar Surface Area) 
40.460 Å2
Source organisms
Homo sapiens (Ref.211) - Human
Carassius auratus (Ref.365) - Bony fish: gold fish
Rosa gallica officinalis (Ref.378) - Land plant: Rosaceae: French rose
Protousnea sp. (Ref.388) - Fungi: lichen
Cladonia sp. (Ref.609) - Fungi: lichen, ascomycetes
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.365 : Masahiro Ohkubo, Miyuki Tsushima, Takashi Maoka, Takao Matsuno, Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology, Volume 124, Issue 3, November 1999, Pages 333–340, "Carotenoids and their metabolism in the goldfish Carassius auratus (Hibuna)".
  • Ref.378 : Maerki-Fischer, Edith; Eugster, Conrad Hans, Helvetica Chimica Acta (1990), 73(5), 1205-9., "Rose pigments. Part 11. New sources of 3'-epilutein in plants".
  • Ref.388 : B. Czeczuga, E. Czeczuga-Semeniuk, S. Calvelo, and S. Liberatore, Journal of Botanical Taxonomy and Geobotany, Volume 116, Issue 3-4, pages 195–200, August 2005, "Carotenoids in representatives of the Protousnea (Parmeliaceae), endemic genus from South America".
  • Ref.609 : Prof. Dr. B. Czeczuga and Doz. Dr. R. Doll, Journal of Botanical Taxonomy and Geobatany, Volume 102, Issue 5-6, pages 431–436, 1991, DOI: 10.1002/fedr.19911020518, "The carotenoid content of lichens of the Cladonia genus from Mecklenburg".
  • CAS
    52842-48-5
    Links to other DB
    KNApSAcK: C00022872
    LipidBank: VCA0028

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