Carotenoids obi
All carotenoids     All organisms   Feedback
Carotenoids DB          Carotenoids DB: CA00403   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible pathways   ]
Entry
CA00403                                                            

Classification
Carotenoid Name
Luteochrome
IUPAC name (5R,6S,5'R,8'RS)-5,6:5',8'-Diepoxy-5,6,5',8'-tetrahydro-beta,beta-carotene
Formula
C40H56O2
Molecular Weight 
568.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Weak MDR reversal activity in mdr1-L1210 and doxorubicin-resistant MCF-7 (Ref.493).
  • Number of
    conjugated double bonds 
    8
    Number of
    conjugated multiple bonds 
    8
    Isomers 
    InChI
    InChI=1S/C40H56O2/c1-30(19-13-20-32(3)23-28-40-37(7,8)25-16-27-39(40,10)42-40)17-11-12-18-31(2)21-14-22-33(4)34-29-35-36(5,6)24-15-26-38(35,9)41-34/h11-14,17-23,28-29,34H,15-16,24-27H2,1-10H3/b12-11+,19-13+,21-14+,28-23+,30-17+,31-18+,32-20+,33-22+/t34?,38-,39-,40+/m1/s1
    InChIKey
    HSOIPJLINDKQOV-FOTQGIOVSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C1C=C2[C@@](O1)(C)CCCC2(C)C)/C)/C)/C=C/C=C(/C=C/[C@]12O[C@]2(C)CCCC1(C)C)\C
    XLogP
    9.981
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    1
    Complexity of molecule
    0.327
    Number of heavy atoms
    42
    TPSA
    (Topological Polar Surface Area) 
    21.760 Å2
    Source organisms
    Pittosporum tobira  - Land plant
    Ipomoea batatas (Ref.291) - Land plant: sweet potato
    Ipomoea batatas Lam. (Ref.295) - Land plant: sweet potato
    References
  • Ref.291 : Ligia Bicudo de Almeida1, Marilene De Vuono Camargo Penteado1, Kenneth L. Simpson2, George Britton, Murat Acemoglu, and Conrad Hans Eugster, Helvetica Chimica Acta Volume 69, Issue 7, pages 1554–1558, 29 October 1986, "Isolation and Characterisation of (5R, 6S,5'R,8'R)- and (5R,6S,5'R,8'S)-Luteochrome from Brazilian Sweet Potatoes (Ipomoea batatas LAM.)".
  • Ref.295 : Ligia B. Almeida, Marilene V.C. Penteado, Journal of Food Composition and Analysis, Volume 1, Issue 4, November 1988, Pages 341–352, "Carotenoids and pro-vitamin A value of white fleshed Brazilian sweet potatoes (Ipomoea batatas Lam.)".
  • Ref.493 : Anne-Laure Gagez, Valérie Thiery, Virginie Pasquet, Jean-Paul Cadoret, and Laurent Picot, Current Bioactive Compounds 2012, 8, 000-000, "Epoxycarotenoids and Cancer. Review".
  • CAS
    6821-08-5
    Links to other DB

       Search other references with Google Scholar