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Entry
CA00703                                                            

Classification
Carotenoid Name
Anhydroprasinoxanthin
IUPAC name (3S,6R,6'S)-3,6-Dihydroxy-2',3'-didehydro-7,8-dihydro-gamma,epsilon-caroten-8-one
Formula
C40H54O3
Molecular Weight 
582.832 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/C40H54O3/c1-29(18-13-19-31(3)23-24-36-32(4)22-15-25-38(36,7)8)16-11-12-17-30(2)20-14-21-33(5)37(42)28-40(43)34(6)26-35(41)27-39(40,9)10/h11-25,35-36,41,43H,6,26-28H2,1-5,7-10H3/b12-11+,18-13+,20-14+,24-23+,29-16+,30-17+,31-19+,33-21+/t35-,36+,40+/m1/s1
InChIKey
NIHNIMGOYVRMKW-PRCBNDTESA-N
Canonical SMILES
O[C@@H]1CC(=C)[C@@](C(C1)(C)C)(O)CC(=O)/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/[C@H]1C(=CC=CC1(C)C)C)\C)\C)/C)/C
XLogP
9.838
Hydrogen Bond donors
(Lipinski's definition)
2
Hydrogen Bond Acceptors
(Lipinski's definition)
3
LipinskiFailures
2
Complexity of molecule
0.309
Number of heavy atoms
43
TPSA
(Topological Polar Surface Area) 
57.530 Å2
Source organisms
Mantoniella squamata (Ref.46, Ref.47) - Green alga: Prasinophyte
Mantoniella squamata  - 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
    168781-51-9
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