Carotenoids obi
All carotenoids     All organisms   Feedback
Carotenoids DB          Carotenoids DB: CA00419   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible pathways   ]
Entry
CA00419                                                            

Classification
Carotenoid Name
Luteoxanthin
IUPAC name (3S,5R,6S,3'S,5'R,8'RS)-5,6:5',8'-Diepoxy-5,6,5',8'-tetrahyrdro-beta,beta-carotene-3,3'-diol
Formula
C40H56O4
Molecular Weight 
600.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Antimicrobial activity - anti-H. pylori (Ref.492).
  • Number of
    conjugated double bonds 
    8
    Number of
    conjugated multiple bonds 
    8
    Isomers 
    InChI
    InChI=1S/C40H56O4/c1-28(17-13-18-30(3)21-22-40-37(7,8)25-33(42)27-39(40,10)44-40)15-11-12-16-29(2)19-14-20-31(4)34-23-35-36(5,6)24-32(41)26-38(35,9)43-34/h11-23,32-34,41-42H,24-27H2,1-10H3/b12-11+,17-13+,19-14+,22-21+,28-15+,29-16+,30-18+,31-20+/t32-,33-,34?,38+,39+,40-/m0/s1
    InChIKey
    YNNRPBRNWWIQPQ-MAAFUUECSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C1C=C2[C@@](O1)(C)C[C@H](CC2(C)C)O)/C)/C)/C=C/C=C(/C=C/[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)\C
    XLogP
    7.710
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    1
    Complexity of molecule
    0.320
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    62.220 Å2
    Source organisms
    Chlamydomonas reinhardtii (Ref.12, Ref.13, Ref.14) - Green alga: Chlamydomonadales, unicellular green alga
    Nannochloropsis oculata (Ref.27, Ref.28) - Alga: Eustigmatophyceae
    Nannochloropsis salina (Ref.27, Ref.28) - Alga: Eustigmatophyceae
    Fucus serratus (Ref.53) - Brown alga: Fucaceae
    Fucus vesiculosus (Ref.53) - Brown alga: Fucaceae
    Pelvetia canaliculata (Ref.53) - Brown alga: Fucaceae
    Ascophyllum nodosum (Ref.53) - Brown alga: Fucaceae
    Laminaria digitata (Ref.53) - Brown alga: Laminariaceae
    Laminaria saccharina (Ref.53) - Brown alga: Laminariaceae
    Curcurbita maxima  - Land plant: pumpkin
    Capsicum annuum var. longum  - Land plant: red spice paprika
    Mangifera indica (Ref.284) - Land plant: mango
    Citrus reticulata (Ref.292) - Land plant: mandarin orange, tangerine
    Citrus sinensis L. Osbeck (Ref.373) - Land plant: orange
    Malus domestica (Ref.492) - Land plant: Rosaceae: apple peel extract
    References
  • Ref.12 : N.I. Krinsky and R. P. Levine, Plant Physiol. Jul 1964; 39(4): 680–687. "Carotenoids of Wild Type and Mutant Strains of the Green Alga, Chlamydomonas reinhardi".
  • Ref.13 : PMID: 1190948: Francis GW, Strand LP, Lien T, Knutsen G., Arch Microbiol. 1975 Aug 28;104(3):249-54. "Variations in the Carotenoid Content of Chlamydomonas reinhardii throughout the Cell cycle".
  • Ref.14 : S. Tkaichi, and M. Mimuro, Plant Cell Physiol. 39(9): 968-977 (1998) "Distribution and Geometric Isomerism of Neoxanthin in Oxygenic Phototrophs: 9'-Cis, a Sole Molecular Form".
  • Ref.27 : N. J. Antial, and J.Y. Cheng, British Phycological Journal, Volume 17, Issue 1, 1982 "The Keto carotenoids of two marine cocoid members of the eustimaphyceae" DOI:10.1080/00071618200650061 .
  • Ref.28 : Luis M. Lubián, Olimpio Montero, Ignacio Moreno-Garrido, I. Emma Huertas, Cristina Sobrino, Manuel González-del Valle, Griselda Parés, Journal of Applied Phycology, October 2000, Volume 12, Issue 3-5, pp 249-255 "Nannochloropsis (Eustigmatophyceae) as source of commercially valuable pigments".
  • Ref.53 : G. Nybraaten, and S. L. Jensen, Acta Chem. Scand. Ser. B, 28,(1974), 485, "Algal Carotenoids. XII. * Chemical Reactions of Carotenoids with 2-Hydroxylated beta-Rings".
  • Ref.284 : Adriana Z. Mercadante ,Délia B. Rodriguez-Amaya, George Britton, J. Agric. Food Chem., 1997, 45 (1), pp 120–123, "HPLC and Mass Spectrometric Analysis of Carotenoids from Mango".
  • Ref.292 : Thomas Wingerath ,Wilhelm Stahl ,Dieter Kirsch, Raimund Kaufmann, and Helmut Sies, J. Agric. Food Chem., 1996, 44 (8), pp 2006–2013, DOI: 10.1021/jf960057y, "Fruit Juice Carotenol Fatty Acid Esters and Carotenoids As Identified by Matrix-Assisted Laser Desorption Ionization (MALDI) Mass Spectrometry".
  • Ref.373 : Kudritskaya, S. E.; Fishman, G. M.; Zagorodskaya, L. M., Subtropicheskie Kul'tury (1977), (5-6), 154-8., "Identification of orange peel (Citrus sinensis Osb.) carotenoids".
  • Ref.492 : Péter Molnár, József Deli, Toru Tanaka,Yoshiyuki Kann, Satoru Tani, Nóra Gyémánt, Joseph Molnár ,and Masami Kawase, Phytotherapy Research, Volume 24, Issue 5, pages 644–648, May 2010, “Carotenoids with anti-Helicobacter pylori activity from Golden deliciousapple”.
  • CAS
    1912-50-1
    Links to other DB
    MassBank: CA000075

       Search other references with Google Scholar