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Entry
CA00620                                                            

Classification
Carotenoid Name
Loroxanthin dodecenoate
IUPAC name (3R,3'R,6'R)-19-Dodec-2-enoyloxy-beta,epsilon-carotene-3,3'-diol
Formula
C52H76O4
Molecular Weight 
765.128 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
10 and 2 (12 in total)
Number of
conjugated multiple bonds 
10 and 2 (12 in total)
Isomers 
InChI
InChI=1S/C52H76O4/c1-11-12-13-14-15-16-17-18-19-30-50(55)56-39-45(32-34-49-44(6)36-47(54)38-52(49,9)10)29-23-28-41(3)25-21-20-24-40(2)26-22-27-42(4)31-33-48-43(5)35-46(53)37-51(48,7)8/h19-35,46-48,53-54H,11-18,36-39H2,1-10H3/b21-20+,26-22+,28-23+,30-19+,33-31+,34-32+,40-24+,41-25+,42-27+,45-29-/t46-,47+,48?/m0/s1
InChIKey
TXBAOQMCVDHBKR-CEIPEQSSSA-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\C1C(=C[C@@H](CC1(C)C)O)C)/C)/C)\C)/C=C/C1=C(C)C[C@H](CC1(C)C)O
XLogP
15.405
Hydrogen Bond donors
(Lipinski's definition)
2
Hydrogen Bond Acceptors
(Lipinski's definition)
4
LipinskiFailures
2
Complexity of molecule
0.227
Number of heavy atoms
56
TPSA
(Topological Polar Surface Area) 
66.760 Å2
Source organisms
Tetraselmis chui (Ref.48) - Green alga: Chlorodendraceae
Tetraselmis marina (Ref.48) - Green alga: Chlorodendraceae
Tetraselmis rubens (Ref.48) - Green alga: Chlorodendraceae
Tetraselmis subcordiformis (Ref.48) - Green alga: Chlorodendraceae
Tetraselmis suecica (Ref.48) - Green alga: Chlorodendraceae
Tetraselmis tetrathele (Ref.48) - Green alga: Chlorodendraceae
Pyramimonas parkeae (Ref.49) - Green alga: Prasinophyte
Tetraselmis chui  - Green alga: Chlorodendraceae
Tetraselmis marina  - Green alga: Chlorodendraceae
Tetraselmis rubens  - Green alga: Chlorodendraceae
Tetraselmis subcordiformis  - Green alga: Chlorodendraceae
Tetraselmis suecica  - Green alga: Chlorodendraceae
Tetraselmis tetrathele  - Green alga: Chlorodendraceae
Pyramimonas parkeae  - Green alga: Prasinophyte
References
  • Ref.48 : Jose L. Carrido, Francisco Rodriguez, and Mannuel Zapata J. Phycol. 15, 366-374 (2009) "Occurrence of Loroxanthin, Loroxanthin decenoate, and Loroxanthin dodecenoate in Tetraselmis species (Prasinophyceae, Chlorophyta)".
  • Ref.49 : T. Sasa, S. Takaichi, N. Hatakeyama, and M. M. Watanabe, Plant Cell Physiol. 33(7): 921-925 (1992) "A novel Carotenoid ester, Loroxanthin Dodecenoate, from Pyramimonas parkeae(Prasinophyceae) and Chlorarachniophycean Alga).".
  • CAS
    144852-84-6
    Links to other DB
    LipidBank: VCA1075

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