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Entry
CA00279                                                            

Classification
Carotenoid Name
3-Hydroxy-4-ketotorulene;
(3R)-3-Hydroxy-4-ketotorulene
IUPAC name 3-Hydroxy-3',4'-didehydro-beta,psi-caroten-4-one
Formula
C40H52O2
Molecular Weight 
564.816 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
14 including one ketone (14 in total)
Number of
conjugated multiple bonds 
14 including one ketone (14 in total)
Isomers 
InChI
InChI=1S/C40H52O2/c1-30(2)17-13-20-33(5)23-15-25-34(6)24-14-21-31(3)18-11-12-19-32(4)22-16-26-35(7)27-28-37-36(8)39(42)38(41)29-40(37,9)10/h11-28,38,41H,29H2,1-10H3/b12-11+,20-13+,21-14+,22-16+,25-15+,28-27+,31-18+,32-19+,33-23+,34-24+,35-26+/t38-/m1/s1
InChIKey
JQSLJBXSPJMQQS-QWXYTXGVSA-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/C=C(/C=C/C=C(C)C)\C)\C
XLogP
12.099
Hydrogen Bond donors
(Lipinski's definition)
1
Hydrogen Bond Acceptors
(Lipinski's definition)
2
LipinskiFailures
2
Complexity of molecule
0.064
Number of heavy atoms
42
TPSA
(Topological Polar Surface Area) 
37.300 Å2
Source organisms
Xanthophyllomyces dendrorhous (Ref.206) - Fungi: red yeast
References
  • 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
    60696-28-8, 496065-81-7
    Links to other DB

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