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Entry
CA00585                                                            

Classification
Carotenoid Name

IUPAC name 5',6'-Epoxy-3'-hydroxy-3-methoxy-4,5-didehydro-5',6'-dihydro-4,6-cyclo-5,6-seco-beta,beta-caroten-5-one
Formula
C41H56O4
Molecular Weight 
612.858 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
11 including one ketone (11 in total)
Number of
conjugated multiple bonds 
11 including one ketone (11 in total)
Isomers 
  • Cis/trans isomer: CA00977
  • Constitutional isomer: CA00586
  • InChI
    InChI=1S/C41H56O4/c1-29(18-14-20-31(3)22-23-35-37(33(5)42)36(44-11)28-38(35,6)7)16-12-13-17-30(2)19-15-21-32(4)24-25-41-39(8,9)26-34(43)27-40(41,10)45-41/h12-25,34,36,43H,26-28H2,1-11H3/b13-12+,18-14+,19-15+,23-22+,25-24+,29-16+,30-17+,31-20+,32-21+/t34-,36?,40+,41-/m0/s1
    InChIKey
    TZVLSBKJAVHHRO-MABFWCCPSA-N
    Canonical SMILES
    COC1CC(C(=C1C(=O)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)\C)\C)/C)/C)(C)C
    XLogP
    9.420
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    2
    Complexity of molecule
    0.297
    Number of heavy atoms
    45
    TPSA
    (Topological Polar Surface Area) 
    59.060 Å2
    Source organisms
    Pittosporum tobira (Ref.310) - Land plant
    References
  • Ref.310 : Fujiwara, Yasuhiro; Maruwaka, Hisashi; Toki, Fujio; Hashimoto, Keiji; Maoka, Takashi, Chemical & Pharmaceutical Bulletin (2001), 49(8), 985-987., "Structure of three new carotenoids with a 3-methoxy-5-keto-5,6-seco-4,6-cyclo-β end group from the seeds of Pittosporum tobira".
  • CAS
    367252-33-3
    Links to other DB
    KNApSAcK: C00023171

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