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Entry
CA00666                                                            

Classification
Carotenoid Name
Siphonaxanthin dodecenoate
IUPAC name (3R,3'R,6'R)-19-(trans-Dodec-2-enoyloxy)-3,3'-dihydroxy-7,8-dihydro-beta,epsilon-caroten-8-one
Formula
C52H76O5
Molecular Weight 
781.128 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9 and 2 including one ketone (11 in total)
Number of
conjugated multiple bonds 
9 and 2 including one ketone (11 in total)
Isomers 
InChI
InChI=1S/C52H76O5/c1-11-12-13-14-15-16-17-18-19-30-50(56)57-38-44(49(55)35-48-43(6)34-46(54)37-52(48,9)10)29-23-28-40(3)25-21-20-24-39(2)26-22-27-41(4)31-32-47-42(5)33-45(53)36-51(47,7)8/h19-33,45-47,53-54H,11-18,34-38H2,1-10H3/b21-20+,26-22+,28-23+,30-19+,32-31+,39-24+,40-25+,41-27+,44-29+/t45-,46+,47-/m0/s1
InChIKey
UERRVASYDCUNEJ-SLVW0.226BSA-N
Canonical SMILES
CCCCCCCCC/C=C/C(=O)OC/C(=C\C=C\C(=C\C=C\C=C(\C=C\C=C(\C=C\[C@H]1C(=C[C@@H](CC1(C)C)O)C)/C)/C)\C)/C(=O)CC1=C(C)C[C@H](CC1(C)C)O
XLogP
14.177
Hydrogen Bond donors
(Lipinski's definition)
2
Hydrogen Bond Acceptors
(Lipinski's definition)
5
LipinskiFailures
2
Complexity of molecule
0.226
Number of heavy atoms
57
TPSA
(Topological Polar Surface Area) 
83.830 Å2
Source organisms
Chlamydomonas parkeae (Ref.15) - Green alga: Chlamydomonadales, unicellular marine flagellate
Pyramimonas amylifera  - Green alga: Prasinophyte
References
  • Ref.15 : T. Sasa, S. Suda, M. M. Watanabe, S. Takaichi, Plant Cell Physiol. 33(5): 527-534(1992) "A novel carotenoid ester, Loroxanthin dodecenoate, from Pyramimonas parkeae (Prasinophyceae) and Chlorarachniophycean alga".
  • CAS
    39704-43-3
    Links to other DB
    LipidBank: VCA1077

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