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Entry
CA00424                                                            

Classification
Carotenoid Name
Vaucheriaxanthin
IUPAC name (3S,5R,6R,3'S,5'R,6'S)-5',6'-Epoxy-6,7-didehydro-5,6,5',6'-tetrahydro-beta,beta-carotene-3,5,3',19'-tetrol
Formula
C40H56O5
Molecular Weight 
616.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9
Number of
conjugated multiple bonds 
9
Isomers 
  • Constitutional isomer: CA01077, CA00512, CA00513, CA00650, CA01080, CA01081
  • InChI
    InChI=1S/C40H56O5/c1-29(16-12-17-31(3)20-21-35-36(4,5)24-33(42)26-38(35,8)44)14-10-11-15-30(2)18-13-19-32(28-41)22-23-40-37(6,7)25-34(43)27-39(40,9)45-40/h10-20,22-23,33-34,41-44H,24-28H2,1-9H3/b11-10+,16-12+,18-13+,23-22+,29-14+,30-15+,31-17+,32-19-/t21?,33-,34-,38+,39+,40-/m0/s1
    InChIKey
    OWWSPDNLRSCPIS-UETBKYIISA-N
    Canonical SMILES
    OC/C(=C\C=C\C(=C\C=C\C=C(\C=C\C=C(\C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)O)/C)/C)\C)/C=C/[C@]12O[C@]2(C)C[C@H](CC1(C)C)O
    XLogP
    8.649
    Hydrogen Bond donors
    (Lipinski's definition)
    4
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    5
    LipinskiFailures
    1
    Complexity of molecule
    0.307
    Number of heavy atoms
    45
    TPSA
    (Topological Polar Surface Area) 
    93.450 Å2
    Source organisms
    Nannochloropsis oculata (Ref.27, Ref.28) - Alga: Eustigmatophyceae
    Nannochloropsis salina (Ref.27, Ref.28) - Alga: Eustigmatophyceae
    Nannochloropsis gaditana (Ref.28) - Alga: Eustigmatophyceae
    References
  • 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".
  • CAS
    29789-80-8
    Links to other DB
    KNApSAcK: C00022947
    LipidBank: VCA1156

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