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Entry
CA00559                                                            

Classification
Carotenoid Name
Astaxanthin monoester
IUPAC name 3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione-3-ester
Formula
C44H58O5
Molecular Weight 
666.904 g/mol
Structure      Search similar carotenoids

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/C44H58O5/c1-12-17-40(46)49-39-29-44(10,11)37(35(7)42(39)48)27-25-33(5)23-16-21-31(3)19-14-13-18-30(2)20-15-22-32(4)24-26-36-34(6)41(47)38(45)28-43(36,8)9/h13-16,18-27,38-39,45H,12,17,28-29H2,1-11H3/b14-13+,20-15+,21-16+,26-24+,27-25+,30-18+,31-19+,32-22+,33-23+
InChIKey
TXEBTMNQELROBS-AYPDHLKJSA-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)O)\C)\C)/C)/C
XLogP
10.829
Hydrogen Bond donors
(Lipinski's definition)
1
Hydrogen Bond Acceptors
(Lipinski's definition)
5
LipinskiFailures
2
Complexity of molecule
0.280
Number of heavy atoms
49
TPSA
(Topological Polar Surface Area) 
80.670 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
Nannochloropsis oculata (Ref.27, Ref.28) - Alga: Eustigmatophyceae
Nannochloropsis salina (Ref.27, Ref.28) - Alga: Eustigmatophyceae
Tovellia sanguinea (Ref.34) - Alga: Dinoflagellate
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.27 : N. J. Antial, and J.Y. Cheng, British Phycological Journal, Volume 17, Issue 1, 1982 "The Keto carotenoids of two marine cocoid members of the eustimaphyceae" DOI:10.1080/00071618200650061 .
  • Ref.28 : Luis M. Lubián, Olimpio Montero, Ignacio Moreno-Garrido, I. Emma Huertas, Cristina Sobrino, Manuel González-del Valle, Griselda Parés, Journal of Applied Phycology, October 2000, Volume 12, Issue 3-5, pp 249-255 "Nannochloropsis (Eustigmatophyceae) as source of commercially valuable pigments".
  • 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".
  • CAS
    622836-59-3
    Links to other DB
    LipidBank: VCA1132

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