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Entry
CA00646                                                            

Classification
Carotenoid Name
Amarouciaxanthin B;
sidnyaxanthin
IUPAC name (3R.6'S)-3,6'-Dihydroxy-7,8-didehydro-7',8'-dihydro-beta,epsilon-carotene-3',8'-dione
Formula
C40H52O4
Molecular Weight 
596.816 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
8 and 2 including two ketones (10 in total)
Number of
conjugated multiple bonds 
10 and 2 including two ketones (12 in total)
Isomers 
InChI
InChI=1S/C40H52O4/c1-28(17-13-18-30(3)21-22-36-32(5)23-34(41)25-38(36,7)8)15-11-12-16-29(2)19-14-20-31(4)37(43)27-40(44)33(6)24-35(42)26-39(40,9)10/h11-20,24,34,41,44H,23,25-27H2,1-10H3/b12-11+,17-13+,19-14+,28-15+,29-16+,30-18+,31-20+/t34-,40-/m1/s1
InChIKey
XUKJTNSSWNXSQU-OMEVNMJGSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)C[C@@]1(O)C(=CC(=O)CC1(C)C)C)/C)/C)/C=C/C=C(/C#CC1=C(C)C[C@H](CC1(C)C)O)\C
XLogP
7.856
Hydrogen Bond donors
(Lipinski's definition)
2
Hydrogen Bond Acceptors
(Lipinski's definition)
4
LipinskiFailures
1
Complexity of molecule
0.312
Number of heavy atoms
44
TPSA
(Topological Polar Surface Area) 
74.600 Å2
Source organisms
Amaroucium pliciferum (Ref.443) - Tunicate
References
  • 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
    92121-55-6
    Links to other DB
    KNApSAcK: C00023061
    LipidBank: VCA0077
    MassBank: CA000143

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