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Entry
CA00500                                                            

Classification
Carotenoid Name
(3R,3'R)-Astaxanthin
IUPAC name (3R,3'R)-3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione
Formula
C40H52O4
Molecular Weight 
596.816 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/C40H52O4/c1-27(17-13-19-29(3)21-23-33-31(5)37(43)35(41)25-39(33,7)8)15-11-12-16-28(2)18-14-20-30(4)22-24-34-32(6)38(44)36(42)26-40(34,9)10/h11-24,35-36,41-42H,25-26H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,27-15+,28-16+,29-19+,30-20+/t35-,36-/m1/s1
InChIKey
MQZIGYBFDRPAKN-OXBRSLPGSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)C(=O)[C@@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/C1=C(C)C(=O)[C@@H](CC1(C)C)O)\C
XLogP
9.696
Hydrogen Bond donors
(Lipinski's definition)
2
Hydrogen Bond Acceptors
(Lipinski's definition)
4
LipinskiFailures
1
Complexity of molecule
0.312
Number of heavy atoms
44
TPSA
(Topological Polar Surface Area) 
74.600 Å2
Source organisms
Xanthophyllomyces dendrorhous (Ref.204, Ref.206) - Fungi: red yeast
References
  • Ref.204 : Tani C, Maoka T, Tani M, Moritomo Y, Okada T, Kitahara G, Katamoto H., J Oleo Sci. 2014;63(9):943-51. Epub 2014 Aug 5., "Accumulation of xanthophylls from the phaffia yeast (Xanthophyllomyces dendrorhrous) in calves.".
  • Ref.206 : Takashi Maoka, Tetsuji Etoh, Ayako Osawa, and Kazutoshi Shindo, Journal of Oleo Science 61, (7), pp.401-406 (2012), "Characterization and Singlet Oxygen Quenching Activity of (3R)-3-Hydroxy-4-Ketotorulene and (3R)-3-Hydroxy-4-Keto-gamma-Carotene from the Yeast Xanthophyllomyces dendrhorous".
  • CAS
    60760-95-4
    Links to other DB
    KNApSAcK: C00023058
    LipidBank: VCA0017

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