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Entry
CA00466                                                            

Classification
Carotenoid Name
Rhodoxanthin
IUPAC name 4',5'-Didehydro-4,5'-retro-beta,beta-carotene-3,3'-dione
Formula
C40H50O2
Molecular Weight 
562.8 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Coloring material for food, beverages, pharmaceuticals and cosmetics (Ref.468).
  • Number of
    conjugated double bonds 
    14 including two ketones (14 in total)
    Number of
    conjugated multiple bonds 
    14 including two ketones (14 in total)
    Isomers 
  • Constitutional isomer: CA00465, CA00464, CA00726
  • InChI
    InChI=1S/C40H50O2/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/h11-26H,27-28H2,1-10H3/b15-11+,16-12+,19-13+,20-14+,29-17+,30-18+,31-21+,32-22+,37-23-,38-24-
    InChIKey
    VWXMLZQUDPCJPL-ZDHAIZATSA-N
    Canonical SMILES
    C/C(=C\C=C\C(=C\C=C/1\C(=CC(=O)CC1(C)C)C)\C)/C=C/C=C/C(=C/C=C/C(=C/C=C\1/C(=CC(=O)CC1(C)C)C)/C)/C
    XLogP
    10.766
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    1
    Complexity of molecule
    0.326
    Number of heavy atoms
    42
    TPSA
    (Topological Polar Surface Area) 
    34.140 Å2
    Source organisms
    Epicoccum nigrum  - Fungi: fungus, a plant pathogen
    Protousnea sp. (Ref.388) - Fungi: lichen
    Cladonia sp. (Ref.609) - Fungi: lichen, ascomycetes
    References
  • 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".
  • 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
    116-30-3
    Links to other DB
    KNApSAcK: C00003784
    LipidBank: VCA0022
    ProCarDB: C1441

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