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Entry
CA00649                                                            

Classification
Carotenoid Name
Amarouciaxanthin A
IUPAC name (3S,5R,6R,6'S)-3,5,6'-Trihydroxy-6,7-didehydro-5,6,7',8'-tetrahydro-beta,epsilon-carotene-3',8'-dione
Formula
C40H54O5
Molecular Weight 
614.832 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9 and 2 including two ketones (11 intotal)
Number of
conjugated multiple bonds 
9 and 2 including one ketone each (11 intotal)
Isomers 
  • Constitutional isomer: CA00511, CA00673, CA00750
  • InChI
    InChI=1S/C40H54O5/c1-28(17-13-18-30(3)21-22-36-37(6,7)24-34(42)26-39(36,10)44)15-11-12-16-29(2)19-14-20-31(4)35(43)27-40(45)32(5)23-33(41)25-38(40,8)9/h11-21,23,34,42,44-45H,24-27H2,1-10H3/b12-11+,17-13+,19-14+,28-15+,29-16+,30-18+,31-20+/t22-,34-,39+,40+/m0/s1
    InChIKey
    NBAOGGCOLYTLDU-VCQLRNSESA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)C[C@]1(O)C(C)(C)CC(=O)C=C1C)/C)/C)/C=C/C=C(/C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)O)\C
    XLogP
    8.445
    Hydrogen Bond donors
    (Lipinski's definition)
    3
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    5
    LipinskiFailures
    1
    Complexity of molecule
    0.303
    Number of heavy atoms
    45
    TPSA
    (Topological Polar Surface Area) 
    94.830 Å2
    Source organisms
    Paphia amabilis (Ref.312) - Shellfish: bivalve, Venus amabilis
    Amaroucium pliciferum (Ref.443) - Tunicate
    References
  • Ref.312 : Maoka, Takashi; Akimoto, Naoshige; Yim, Mi-Jin; Hosokawa, Masashi; Miyashita, Kazuo, Journal of Agricultural and Food Chemistry (2008), 56(24), 12069-12072., "New C37 Skeletal Carotenoid from the Clam, Paphia amabillis".
  • Ref.443 : Takao Matsuno, Masahiro Ookubo, Tadaaki Komori, J. Nat. Prod., 1985, 48 (4), pp 606–613, DOI: 10.1021/np50040a015"Carotenoids of Tunicates, III. The Structural Elucidation of Two New Marine Carotenoids, Amarouciaxanthin A and B".
  • CAS
    100667-78-5
    Links to other DB
    KNApSAcK: C00023066
    LipidBank: VCA0076
    MassBank: CA000142

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