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Entry
CA00701                                                            

Classification
Carotenoid Name
Prasinoxanthin
IUPAC name (3S,6R,3'R,6'R)-3,6,3'-Trihydroxy-7,8-dihydro-gamma,epsilon-caroten-8-one
Formula
C40H56O4
Molecular Weight 
600.848 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/C40H56O4/c1-28(17-13-18-30(3)21-22-36-32(5)23-34(41)25-38(36,7)8)15-11-12-16-29(2)19-14-20-31(4)37(43)27-40(44)33(6)24-35(42)26-39(40,9)10/h11-23,34-36,41-42,44H,6,24-27H2,1-5,7-10H3/b12-11+,17-13+,19-14+,22-21+,28-15+,29-16+,30-18+,31-20+/t34-,35+,36-,40-/m0/s1
InChIKey
WOJYJHBMWRNRJG-DTJZQRCSSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)C[C@]1(O)C(=C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/[C@H]1C(=C[C@@H](CC1(C)C)O)C)\C
XLogP
8.661
Hydrogen Bond donors
(Lipinski's definition)
3
Hydrogen Bond Acceptors
(Lipinski's definition)
4
LipinskiFailures
2
Complexity of molecule
0.300
Number of heavy atoms
44
TPSA
(Topological Polar Surface Area) 
77.760 Å2
Source organisms
Bathycoccus prasinos (Ref.46) - Green alga: Prasinophyte
Mantoniella squamata (Ref.46, Ref.47) - Green alga: Prasinophyte
Micromonas pusilla (Ref.46, Ref.47) - Green alga: Prasinophyte
Arousa sp. (Ref.46) - Green alga: Prasinophyte
Prasinococcus capsulatus (Ref.46) - Green alga: Prasinophyte
Pycnococcus provasolii (Ref.46) - Green alga: Prasinophyte
Pseudoscourfieldia marina (Ref.46) - 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
    94705-97-2
    Links to other DB
    LipidBank: VCA1118

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