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Entry
CA01134                                                            

Classification
Carotenoid Name
3-Hydroxy-α-Ionone;
3-Hydroxy-alpha-Ionone
IUPAC name (3R,6R)-3-Hydroxy-9,10-dihydro-9-apo-epsilon-caroten-9-one
Formula
C13H20O2
Molecular Weight 
208.29 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Volatile constitution of Rosaceae (Ref.553).
  • Number of
    conjugated double bonds 
    3 including one ketone (3 in total)
    Number of
    conjugated multiple bonds 
    3 including one ketone (3 in total)
    Isomers 
    InChI
    InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-7,11-12,15H,8H2,1-4H3/b6-5+/t11-,12-/m0/s1
    InChIKey
    FDSNVAKZRJLMJN-WTIVYXKASA-N
    Canonical SMILES
    CC(=O)/C=C/[C@H]1C(=C[C@@H](CC1(C)C)O)C
    XLogP
    2.284
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    0
    Complexity of molecule
    0.171
    Number of heavy atoms
    15
    TPSA
    (Topological Polar Surface Area) 
    37.300 Å2
    Source organisms
    Arabidopsis thaliana (Ref.551) - Land plant: thale-cress, a model organism
    Galleria mellonella (Ref.558) - Insect: greater wax moth
    References
  • Ref.551 : Steven H. Schwartz, Xiaoqiong Qin, and Jan A. D. Zeevaart, THE JOURNAL OF BIOLOGICAL CHEMISTRY, Vol. 276, No. 27, Issue of July 6, pp. 25208–25211, 2001, "Characterization of a Novel Carotenoid Cleavage Dioxygenase from Plants".
  • Ref.558 : Vitus Oberhausera, Olaf Voolstraa, Annette Bangerta, Johannes von Lintigb, and Klaus Vogt, Proc Natl Acad Sci U S A. 2008 Dec 2;105(48):19000-5. doi: 10.1073/pnas.0807805105. Epub 2008 Nov 19., "NinaB combines carotenoid oxygenase and retinoid isomerase activity in a single polypeptide.".
  • Ref.553 : Dana Tatman, Huanbiao Mo, Cancer Letters 175 (2002) 129–139, "Volatile isoprenoid constituents of fruits, vegetables and herbs cumulatively suppress the proliferation of murine B16 melanoma and human HL-60 leukemia cells".
  • CAS

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