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Entry
CA00667                                                            

Classification
Carotenoid Name
Siphonein
IUPAC name (3R,3'R,6'R)-19-Dodecanoyloxy-3,3'-dihydroxy-7,8,-dihydro-beta,epsilon-caroten-8-one
Formula
C52H78O5
Molecular Weight 
783.144 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9 including one ketone (9 in total)
Number of
conjugated multiple bonds 
9 including one ketone (9 in total)
Isomers 
InChI
InChI=1S/C52H78O5/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/h20-29,31-33,45-47,53-54H,11-19,30,34-38H2,1-10H3/b21-20+,26-22+,28-23+,32-31+,39-24+,40-25+,41-27+,44-29+/t45-,46+,47-/m0/s1
InChIKey
IGIZEJMGIZMFNB-XCIBEMBJSA-N
Canonical SMILES
CCCCCCCCCCCC(=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
14.288
Hydrogen Bond donors
(Lipinski's definition)
2
Hydrogen Bond Acceptors
(Lipinski's definition)
5
LipinskiFailures
2
Complexity of molecule
0.222
Number of heavy atoms
57
TPSA
(Topological Polar Surface Area) 
83.830 Å2
Source organisms
Euglena viridis (Ref.44) - Alga: Euglenoid
Eutreptiella gymnastica (Ref.45) - Alga: Euglenoid
Pyramimonas amylifera (Ref.46) - Green alga: Prasinophyte
Codium fragile  - Green alga: Ulvophyceae
References
  • Ref.44 : A. Fiksdahl, S. Liaaen-Jensen, Phytochemistry, Vol.27, No.5, pp. 1447 - 1450, 1988 "Diacetylenic carotenoids from Euglena viridis".
  • Ref.45 : A. Fiksdahl, T. Bjoernland, and S. Liaaen-Jensen, Phytochemistry, Vol. 23, No.3, pp. 649-655, 1984, "Algal carotenoids with novel end groups".
  • Ref.46 : E. S. Egeland, R. R. L. Guillard, and S. Liaaen-Jensen, Phytochemistry, Vol. 44, No. 6, pp.1087-1097, 1997, "Additional carotenoid prototype representatices and general chemosystematic evaluation of carotenoids in prasinophyceae (chlorophyta)".
  • CAS
    39704-43-3
    Links to other DB

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