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Entry
CA00563                                                            

Classification
Carotenoid Name
Astaxanthin diester
IUPAC name 3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione-3,3'-diester
Formula
C48H64O6
Molecular Weight 
736.992 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
13 including two ketones (13 in total)
Number of
conjugated multiple bonds 
13 including two ketones (13 in total)
Isomers 
InChI
InChI=1S/C48H64O6/c1-13-19-43(49)53-41-31-47(9,10)39(37(7)45(41)51)29-27-35(5)25-17-23-33(3)21-15-16-22-34(4)24-18-26-36(6)28-30-40-38(8)46(52)42(32-48(40,11)12)54-44(50)20-14-2/h15-18,21-30,41-42H,13-14,19-20,31-32H2,1-12H3/b16-15+,23-17+,24-18+,29-27+,30-28+,33-21+,34-22+,35-25+,36-26+
InChIKey
YLHPQHRTJIUYAV-FLOONPIKSA-N
Canonical SMILES
CCCC(=O)OC1CC(C)(C)C(=C(C1=O)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(C)C(=O)C(CC1(C)C)OC(=O)CCC)\C)\C)/C)/C
XLogP
11.962
Hydrogen Bond donors
(Lipinski's definition)
0
Hydrogen Bond Acceptors
(Lipinski's definition)
6
LipinskiFailures
2
Complexity of molecule
0.254
Number of heavy atoms
54
TPSA
(Topological Polar Surface Area) 
86.740 Å2
Source organisms
Neochloris wimmeri  - Green alga: Scenedesmaceae
Ettlia carotinosa (Ref.16) - Green alga: Chlamydomonadales
Protosiphon botryoides (Ref.16, Ref.17) - Green alga: Chlamydomonadales
Scotiellopsis oocystiformis (Ref.16) - Green alga: Scenedesmaceae
Scenedesmus vacuolatus (Ref.16) - Green alga: Scenedesmaceae
Chlorella zofingiensis (Ref.16) - Green alga: Scenedesmaceae
Tovellia sanguinea (Ref.34) - Alga: Dinoflagellate
Euglena sanguinea (Ref.43) - Alga: Euglenoid
References
  • Ref.16 : M. Orosa, E. Torres, P. Fidalgo, J. Abalde, Journal of Applied Phycology, October 2000, Volume 12, Issue 3-5, pp 553-556 "Production and analysis of secondary carotenoids in green algae".
  • Ref.17 : H. Kleinig and F. C. Czygan (1969), Z Naturforsch B. 1969 Jul;24(7):927-30. "Lipids of Protosiphon (Chlorophyta) Carotenoids and Carotenoid Esters of five Strains of Protosiphon botryoides Klebs" .
  • Ref.34 : R. Frassanito G. Flaim, I. Mancini, G. Guella, Biochemical Systematics and Ecology 34 (2006) pp.843-853, "High production of unexpected carotenoids in Dinophyceae. Astaxanthin esters from freshwater dinoflagellate Tovellia sanguinea".
  • Ref.43 : Merte grung et.al, S. Liaaen-Jensen, Biochemical Systematics and Ecology, Vol. 21, No. 8, pp. 757-763, 1993 "Algal Carotenoids52*; Secondary carotenoids of Algae 3; Carotenoids in natural bloom of Euglena sanguinea".
  • CAS
    622836-60-6
    Links to other DB
    LipidBank: VCA1132

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