Carotenoids obi
All carotenoids     All organisms   Feedback
Carotenoids DB          Carotenoids DB: CA00264   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible pathways   ]
Entry
CA00264                                                            

Classification
Carotenoid Name
Flexixanthin
IUPAC name (3S)-3,1'-Dihydroxy-3',4'-didehydro-1',2'-dihydro-beta,psi-caroten-4-one
Formula
C40H54O3
Molecular Weight 
582.832 g/mol
Structure   
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/C40H54O3/c1-30(19-13-21-32(3)22-14-23-33(4)25-16-28-40(9,10)43)17-11-12-18-31(2)20-15-24-34(5)26-27-36-35(6)38(42)37(41)29-39(36,7)8/h11-27,37,41,43H,28-29H2,1-10H3/b12-11+,19-13+,20-15+,22-14+,25-16+,27-26+,30-17+,31-18+,32-21+,33-23+,34-24+/t37-/m0/s1
InChIKey
LLKMUZAISVDKFO-PJPUVCQISA-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/CC(O)(C)C)\C)\C
XLogP
10.919
Hydrogen Bond donors
(Lipinski's definition)
2
Hydrogen Bond Acceptors
(Lipinski's definition)
3
LipinskiFailures
2
Complexity of molecule
0.062
Number of heavy atoms
43
TPSA
(Topological Polar Surface Area) 
57.530 Å2
Source organisms
Flexibacter strain NIVA (Ref.244) - Bacteroidetes
Algoriphagus sp. (Ref.357) - CFB group bacteria: orange-pigmented bacterium isolated from marine sponge
References
  • 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.357 : Luan Tao · Henry Yao · Hiroaki Kasai, Norihiko Misawa · Qiong Cheng, Mol Gen Genomics (2006), "A carotenoid synthesis gene cluster from Algoriphagus sp. KK10202C with a novel fusion-type lycopene -cyclase gene".
  • CAS
    14685-41-7
    Links to other DB
    KNApSAcK: C00023010
    LipidBank: VCA1020
    ProCarDB: C1437

       Search other references with Google Scholar