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Entry
CA00627                                                            

Classification
Carotenoid Name
Lutein epoxide;
Lutein-epoxide;
Lutein 5,6-epoxide;
Taraxanthin;
Isolutein
IUPAC name (3S,5R,6S,3'R,6'R)-5,6-Epoxy-5,6-dihydro-beta,epsilon-carotene-3,3'-diol
Formula
C40H56O3
Molecular Weight 
584.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Photosynthetic pigment of higher plants (Ref.503).
  • Xanthophyll cycle pigment (Ref.470).
  • Yellow pigment (Ref.468).
  • Number of
    conjugated double bonds 
    9
    Number of
    conjugated multiple bonds 
    9
    Isomers 
    InChI
    InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40-38(8,9)27-35(42)28-39(40,10)43-40/h11-25,34-36,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,22-21+,24-23+,29-15+,30-16+,31-19+,32-20+/t34-,35-,36-,39+,40-/m0/s1
    InChIKey
    DYUUPIKEWLHQGQ-FJOIUHRLSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\[C@]12O[C@]2(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
    10.483
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    1
    Complexity of molecule
    0.313
    Number of heavy atoms
    43
    TPSA
    (Topological Polar Surface Area) 
    52.990 Å2
    Source organisms
    Protosiphon botryoides (Ref.16, Ref.17) - Green alga: Chlamydomonadales
    Cladonia sp. (Ref.609) - Fungi: lichen, ascomycetes
    References
  • Ref.16 : M. Orosa, E. Torres, P. Fidalgo, J. Abalde, Journal of Applied Phycology, October 2000, Volume 12, Issue 3-5, pp 553-556 "Production and analysis of secondary carotenoids in green algae".
  • Ref.17 : H. Kleinig and F. C. Czygan (1969), Z Naturforsch B. 1969 Jul;24(7):927-30. "Lipids of Protosiphon (Chlorophyta) Carotenoids and Carotenoid Esters of five Strains of Protosiphon botryoides Klebs" .
  • 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".
  • Ref.503 : Javier de las Rivas, Anunciacion Abadia, and Javier Abadia, Plant Physiol. (1989) 91, 190-192, “A New Reversed Phase-HPLC Method Resolving All Major Higher Plant Photosynthetic Pigments1”.
  • Ref.470 : Esteban R1, Jiménez ET, Jiménez MS, Morales D, Hormaetxe K, Becerril JM, García-Plazaola JI., Tree Physiol. 2007 Oct;27(10):1407-14., "Dynamics of violaxanthin and lutein epoxide xanthophyll cycles in Lauraceae tree species under field conditions.".
  • Ref.468 : Gerard P. Moss, Herbert Baxter, J.B. Harborne, Gerald P. Moss, CRC Press; 1 edition (February 15, 1993), ISBN-10: 0850667364, ISBN-13: 978-0850667363, "Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants".
  • CAS
    28368-08-3
    Links to other DB
    KNApSAcK: C00003777
    MassBank: CA000068

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