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Entry
CA01073                                                            

Classification
Carotenoid Name
Heteranthin
IUPAC name Methyl-3-oxo-12'-apo-epsilon,psi-caroten-12'-oate
Formula
C26H34O3
Molecular Weight 
394.532 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Antioxidant activity comparable to astaxanthin (Ref.477).
  • Antiradical activity (Ref.477).
  • Yellow color - absorption maxima at 237, 283, 323, 359, and 405nm (Ref.477).
  • Number of
    conjugated double bonds 
    7 including one ketone and one carboxylic acid methyl ester (7 in total)
    Number of
    conjugated multiple bonds 
    7 including one ketone and one carboxylic acid methyl ester (7 in total)
    Isomers 
    InChI
    InChI=1S/C26H34O3/c1-19(11-8-9-14-21(3)25(28)29-7)12-10-13-20(2)15-16-24-22(4)17-23(27)18-26(24,5)6/h8-17,24H,18H2,1-7H3/b9-8+,12-10+,16-15+,19-11+,20-13+,21-14+/t24-/m1/s1
    InChIKey
    NRLVZXUWVPUCFW-WFCITUQGSA-N
    Canonical SMILES
    COC(=O)/C(=C/C=C/C=C(/C=C/C=C(/C=C/[C@@H]1C(=CC(=O)CC1(C)C)C)\C)\C)/C
    XLogP
    6.505
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    1
    Complexity of molecule
    0.095
    Number of heavy atoms
    29
    TPSA
    (Topological Polar Surface Area) 
    43.370 Å2
    Source organisms
    Ditaxis heterantha (Ref.477) - Land plant: azafrán, azafrancillo
    References
  • Ref.477 : Marıa D. Mendez-Robles, Herry H. Permady, Marıa E. Jaramillo-Flores, Eugenia C. Lugo-Cervantes, Anaberta Cardador-Martınez, Alejandro A. Canales-Aguirre, Fernando Lopez-Dellamary, Carlos M. Cerda-Garcı´a-Rojas, and Joaquın Tamariz, J. Nat. Prod. 2006, 69, 1140-1144, "C-26 and C-30 Apocarotenoids from Seeds of Ditaxis heterantha with Antioxidant Activity and Protection against DNA Oxidative Damage".
  • CAS

    Links to other DB
    KNApSAcK: C00041588

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