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Entry
CA00674                                                            

Classification
Carotenoid Name
Anhydrouriolide
IUPAC name (3S,5R,6S,6'S)-5,6-Epoxy-3-hydroxy-2',3'-didehydro-5,6,7',8'-tetrahydro-beta,epsilon-caroten-19',11'-olide
Formula
C40H52O4
Molecular Weight 
596.816 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9 and 2 including one lactone (11 in total)
Number of
conjugated multiple bonds 
9 and 2 including one lactone (11 in total)
Isomers 
InChI
InChI=1S/C40H52O4/c1-28(16-12-17-29(2)21-23-40-38(7,8)26-33(41)27-39(40,9)44-40)14-10-11-15-30(3)24-34-25-32(36(42)43-34)19-20-35-31(4)18-13-22-37(35,5)6/h10-18,21-25,33,35,41H,19-20,26-27H2,1-9H3/b11-10+,16-12+,23-21+,28-14+,29-17+,30-15+,34-24-/t33-,35-,39+,40-/m0/s1
InChIKey
ZKTIVYXHMCZVOI-FUZVIZNDSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C/1\C=C(C(=O)O1)CC[C@H]1C(=CC=CC1(C)C)C)/C)/C=C/C=C(/C=C/[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)\C
XLogP
9.766
Hydrogen Bond donors
(Lipinski's definition)
1
Hydrogen Bond Acceptors
(Lipinski's definition)
4
LipinskiFailures
1
Complexity of molecule
0.344
Number of heavy atoms
44
TPSA
(Topological Polar Surface Area) 
59.060 Å2
Source organisms
Mantoniella squamata (Ref.46, Ref.47) - Green alga: Prasinophyte
Micromonas pusilla (Ref.46, Ref.47) - Green alga: Prasinophyte
References
  • 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)".
  • Ref.47 : E. S. Egeland, W. Eikrem, J. Throndsen, C. Wilhelm, M. Zapata, and S. Liaaen-Jensen, Biochemical systematics and Ecology, Vol. 23, NO. 7/8, pp. 747-755, 1995 "Carotenoids from Further Prasinophytes".
  • CAS
    168781-48-4
    Links to other DB
    KNApSAcK: C00023074

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