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Entry
CA00284                                                            

Classification
Carotenoid Name
Torularhodin methyl ester;
P 497
IUPAC name Methyl 3',4'-didehydro-beta,psi-caroten-16'-oate
Formula
C41H54O3
Molecular Weight 
594.842 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
14 including one caroboxylic acid methyl ester (14 in total)
Number of
conjugated multiple bonds 
14 including one caroboxylic acid methyl ester (14 in total)
Isomers 
  • Constitutional isomer: CA00496, CA00645
  • InChI
    InChI=1S/C41H54O3/c1-31(19-13-21-33(3)22-14-23-34(4)25-16-26-36(6)40(43)44-10)17-11-12-18-32(2)20-15-24-35(5)27-28-39-37(7)29-38(42)30-41(39,8)9/h11-28,38,42H,29-30H2,1-10H3/b12-11+,19-13+,20-15+,22-14+,25-16+,28-27+,31-17+,32-18+,33-21+,34-23+,35-24+,36-26+/t38-/m1/s1
    InChIKey
    YEWLELSMUHRXKD-SFCQWOQXSA-N
    Canonical SMILES
    COC(=O)/C(=C/C=C/C(=C/C=C/C(=C/C=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
    XLogP
    11.399
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    2
    Complexity of molecule
    0.061
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    46.530 Å2
    Source organisms
    Cookeina sulcipes (Ref.218) - Fungi: mushroom
    Protousnea sp. (Ref.388) - Fungi: lichen
    References
  • Ref.218 : Arpin, Noel; Liaaen Jensen, Synnoeve, Comptes Rendus des Seances de l'Academie des Sciences, Serie D:  Sciences Naturelles (1967), 265(15), 1083-5., "Chemotaxonomic study of fungi.  Presence of torularhodin methyl ester in Cookeina sulcipes".
  • 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".
  • CAS
    20186-11-2
    Links to other DB
    KNApSAcK: C00023073

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