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Entry
CA00266                                                            

Classification
Carotenoid Name
4-Ketomyxol;
2'-Hydroxyflexixanthin
IUPAC name (3S,2'S)-3,1',2'-Trihydroxy-3',4'-didehydro-1',2'-dihydro-beta,psi-caroten-4-one
Formula
C40H54O4
Molecular Weight 
598.832 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
13 including one ketone (13 in total)
Number of
conjugated multiple bonds 
13 including one ketone (13 in total)
Isomers 
InChI
InChI=1S/C40H54O4/c1-29(18-13-20-31(3)21-15-23-33(5)25-27-37(42)40(9,10)44)16-11-12-17-30(2)19-14-22-32(4)24-26-35-34(6)38(43)36(41)28-39(35,7)8/h11-27,36-37,41-42,44H,28H2,1-10H3/b12-11+,18-13+,19-14+,21-15+,26-24+,27-25+,29-16+,30-17+,31-20+,32-22+,33-23+/t36-,37-/m0/s1
InChIKey
KNOCSVIWFHUSCQ-ZZQJGDSCSA-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@@H](C(O)(C)C)O)\C)\C
XLogP
9.944
Hydrogen Bond donors
(Lipinski's definition)
3
Hydrogen Bond Acceptors
(Lipinski's definition)
4
LipinskiFailures
2
Complexity of molecule
0.061
Number of heavy atoms
44
TPSA
(Topological Polar Surface Area) 
77.760 Å2
Source organisms
Anabaena variabilis ATCC 29413 (Ref.527) - Cyanobacteria
Flexibacter strain NIVA (Ref.244) - Bacteroidetes
Flexibacter sp. (Ref.246) - Bacteroidetes
References
  • Ref.527 : Shinichi Takaichi, Mari Mochimaru, and Takashi Maoka, Plant Cell Physiol. 47(2): 211–216 (2006), doi:10.1093/pcp/pci236, "Presence of Free Myxol and 4-Hydroxymyxol and Absence of Myxol Glycosides in Anabaena variabilis ATCC 29413, and Proposal of a Biosynthetic Pathway of Carotenoids".
  • Ref.244 : Andrewes, Arthur G.; Foss, Per; Borch, Gunner; Liaaen-Jensen, Synnoeve, Acta Chemica Scandinavica, Series B:  Organic Chemistry and Biochemistry (1984), B38(4), 337-9., "Bacterial carotenoids. 50. On the structures of (3S)-flexixanthin and (3S,2'S)-2'-hydroxyflexixanthin".
  • Ref.246 : Coman, Ruth E.; Weedon, Basil C. L., Journal of the Chemical Society, Perkin Transactions 1:  Organic and Bio-Organic Chemistry (1972-1999) (1975), (23), 2529-32., "Carotenoids and related compounds.  XXXIII.  Synthesis of dehydroflexixanthin and deoxyflexixanthin".
  • CAS
    38715-22-9
    Links to other DB
    KNApSAcK: C00023026
    LipidBank: VCA1021

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