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Entry
CA00169                                                            

Classification
Carotenoid Name
Phillipsiaxanthin
IUPAC name 1,1'-Dihydroxy-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-psi,psi-carotene-2,2'-dione
Formula
C40H52O4
Molecular Weight 
596.816 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Deep purple color (Ref.585).
  • Number of
    conjugated double bonds 
    15 including two ketones (15 in total)
    Number of
    conjugated multiple bonds 
    15 including two ketones (15 in total)
    Isomers 
    InChI
    InChI=1S/C40H52O4/c1-31(19-13-21-33(3)23-15-25-35(5)27-29-37(41)39(7,8)43)17-11-12-18-32(2)20-14-22-34(4)24-16-26-36(6)28-30-38(42)40(9,10)44/h11-30,43-44H,1-10H3/b12-11+,19-13+,20-14+,23-15+,24-16+,29-27+,30-28+,31-17+,32-18+,33-21+,34-22+,35-25+,36-26+
    InChIKey
    UERCYYLOKQAWFG-ZDXQBWOGSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C=C(\C=C\C(=O)C(O)(C)C)/C)/C)/C)/C=C/C=C(/C=C/C=C(/C=C/C(=O)C(O)(C)C)\C)\C
    XLogP
    9.564
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    74.600 Å2
    Source organisms
    Rubrivivax gelatinosus (Ref.108) - Betaproteobacteria: phototrophic purple nonsulfur bacteria
    Leccinum griseum (Ref.109) - Fungi: mushroom
    Leccinum scabrum (Ref.109) - Fungi: mushroom
    Leccinum testaceo-scabrum (Ref.109) - Fungi: mushroom
    Phillipsia carminea (Ref.110) - Fungi: mushroom
    References
  • Ref.108 : Pinta, Violaine; Ouchane, Soufian; Picaud, Martine; Takaichi, Shinichi; Astier, Chantal; Reiss-Husson, Francoise, Archives of Microbiology (2003), 179(5), 354-362., "Characterization of unusual hydroxy- and ketocarotenoids in Rubrivivax gelatinosus: involvement of enzyme CrtF or CrtA".
  • Ref.109 : Czeczuga, B., Qualitas Plantarum - Plant Foods for Human Nutrition (1978), 28(3), 197-201., "Investigations on carotenoids in fungi. V. Representatives of the Leccinum genus".
  • Ref.110 : Arpin, Noel; Liaaen Jensen, Synnoeve, Bulletin de la Societe de Chimie Biologique (1967), 49(5), 527-361., "Chemotaxonomic studies on fungi. Fungal carotenoids. IV. Phillipsia carminea carotenoids. Isolation and identification of a new, naturally occurring xanthophyll".
  • Ref.585 : Pyung Cheon Lee, Abu Zafar Ruhul Momen, Benjamin N. Mijts, and Claudia Schmidt-Dannert, Chemistry & Biology, Vol. 10, 453–462, May, 2003, 2003 Elsevier Science Ltd. All rights reserved. DOI 10.1016/S1074-5521(03)00103-0, "Biosynthesis of Structurally Novel Carotenoids in Escherichia coli".
  • CAS
    18416-92-7
    Links to other DB
    KNApSAcK: C00023063

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