Carotenoids obi
All carotenoids     All organisms   Feedback
Carotenoids DB          Carotenoids DB: CA00460   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible pathways   ]
Entry
CA00460                                                            

Classification
Carotenoid Name
2-Keto-3,4-dehydro-β-carotene;
3,4-didehydro-β-caroten-2-one;
2-Keto-3,4-dehydro-beta-carotene;
3,4-didehydro-beta-caroten-2-one
IUPAC name 3,4-Didehydro-beta,beta-caroten-2-one
Formula
C40H52O
Molecular Weight 
548.816 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
13 including one ketone (13 in total)
Number of
conjugated multiple bonds 
13 including one ketone (13 in total)
Isomers 
  • Constitutional isomer: CA00160, CA00254, CA00255, CA00320, CA00364, CA00540, CA00724, CA00729
  • InChI
    InChI=1S/C40H52O/c1-30(18-13-20-32(3)23-26-36-34(5)22-15-29-39(36,7)8)16-11-12-17-31(2)19-14-21-33(4)24-27-37-35(6)25-28-38(41)40(37,9)10/h11-14,16-21,23-28H,15,22,29H2,1-10H3/b12-11+,18-13+,19-14+,26-23+,27-24+,30-16+,31-17+,32-20+,33-21+
    InChIKey
    WOXFCLQUFVJAEV-VTSYBOBWSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)C=CC(=O)C1(C)C)/C)/C)/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C
    XLogP
    12.725
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    1
    Complexity of molecule
    0.323
    Number of heavy atoms
    41
    TPSA
    (Topological Polar Surface Area) 
    17.070 Å2
    Source organisms
    Anisomorpha buprestoides (Ref.305) - Insect: walking stick
    Neophirasea japonica (Ref.306) - Insect: walking stick
    Extatosoma tiaratum (Ref.308) - Insect: giant prickly stick insect
    References
  • Ref.305 : Davidson, Bradley S.; Eisner, Thomas; Meinwald, Jerrold, Tetrahedron Letters (1991), 32(41), 5651-4., "3,4-Didehydro-β,β-caroten-2-one, a new carotenoid from the eggs of the stick insect Anisomorpha buprestoides".
  • Ref.306 : Matsuno, Takao; Maoka, Takashi; Toriiminami, Yutaka, Comparative Biochemistry and Physiology, Part B:  Biochemistry & Molecular Biology (1990), 95B(3), 583-7., "Carotenoids in the Japanese stick insect Neophirasea japonica".
  • Ref.308 : Kayser, Hartmut, Zeitschrift fuer Naturforschung, C:  Journal of Biosciences (1981), 36C(9-10), 755-64., "Carotenoids in the stick insect, Ectatosoma tiaratum.  Isolation of β,ε-carotene-2-ol and β,ε-carotene-2-one".
  • CAS
    130177-40-1
    Links to other DB
    KNApSAcK: C00022966

       Search other references with Google Scholar