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Entry
CA00148                                                            

Classification
Carotenoid Name
Phytoene epoxide
IUPAC name 1,2-Epoxy-1,2,7,8,11,12,7',8',11',12'-decahydro-psi,psi-carotene
Formula
C40H64O
Molecular Weight 
560.912 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
3
Number of
conjugated multiple bonds 
3
Isomers 
  • Constitutional isomer: CA00132, CA00237
  • InChI
    InChI=1S/C40H64O/c1-32(2)18-13-21-35(5)24-16-27-36(6)25-14-22-33(3)19-11-12-20-34(4)23-15-26-37(7)28-17-29-38(8)30-31-39-40(9,10)41-39/h11-12,18-20,24-26,29,39H,13-17,21-23,27-28,30-31H2,1-10H3/b12-11+,33-19+,34-20+,35-24+,36-25+,37-26+,38-29+
    InChIKey
    BCPVRLMAESAYCE-PTJVDYMASA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\CC/C=C(/CC/C=C(/CCC1OC1(C)C)\C)\C)/C)/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C
    XLogP
    13.423
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    2
    Complexity of molecule
    0.029
    Number of heavy atoms
    41
    TPSA
    (Topological Polar Surface Area) 
    12.530 Å2
    Source organisms
    Scenedesmus acutus (Ref.50) - Green alga: Scenedesmaceae
    Lycopersicon esculentum (Ref.346) - Land plant: Solanaceae: tomato
    References
  • Ref.50 : M. Albrecht, G. Sandmann, D. Musker, and G. Britton, J. Agric. Food Chem. 1991, 38, 566-569, "Identification of Epoxy and Hydroxyphytoene from Norflurazon-Treated Scenedesmus".
  • Ref.346 : Avraham Ben-Aziz, George Britton, Trevor W. Goodwin, Phytochemistry, Volume 12, Issue 11, November 1973, Pages 2759-2764, "Carotene epoxides of Lycopersicon esculentum".
  • CAS
    26107-96-0
    Links to other DB
    KNApSAcK: C00022939

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