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Entry
CA00346                                                            

Classification
Carotenoid Name
Nostoxanthin
IUPAC name (2R,3R,2'R,3'R)-beta,beta-Carotene-2,3,2',3'-tetrol
Formula
C40H56O4
Molecular Weight 
600.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
11
Number of
conjugated multiple bonds 
11
Isomers 
InChI
InChI=1S/C40H56O4/c1-27(17-13-19-29(3)21-23-33-31(5)25-35(41)37(43)39(33,7)8)15-11-12-16-28(2)18-14-20-30(4)22-24-34-32(6)26-36(42)38(44)40(34,9)10/h11-24,35-38,41-44H,25-26H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,27-15+,28-16+,29-19+,30-20+/t35-,36-,37+,38+/m1/s1
InChIKey
JVPASJUYZJKFHY-HWFHZMFDSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)C[C@H]([C@@H](C1(C)C)O)O)/C)/C)/C=C/C=C(/C=C/C1=C(C)C[C@H]([C@@H](C1(C)C)O)O)\C
XLogP
8.096
Hydrogen Bond donors
(Lipinski's definition)
4
Hydrogen Bond Acceptors
(Lipinski's definition)
4
LipinskiFailures
1
Complexity of molecule
0.300
Number of heavy atoms
44
TPSA
(Topological Polar Surface Area) 
80.920 Å2
Source organisms
Nostoc commune (Ref.1) - Cyanobacteria: star jelly, witch's butter, mare's eggs, fah-tsai and facai, eaten as a salad
Calothrix parietina (Ref.1) - Cyanobacteria: a hair-forming cyanobacteria rom an upland stream
Anacystis nidulans (Ref.1) - Cyanobacteria: other name is Synechococcus elongatus PCC 7942
Synechococcus elongatus (Ref.1) - Cyanobacteria: freshwater unicellular cyanobacterium
Erythrobacter longus (Ref.364) - Alphaproteobacteria: marine anoxygenic phototroph with BChl a
References
  • Ref.1 : S. Hertzberg, S. Liaaen-Jensen, and H. W. Siegelman, Phytochemistry, 1971, Vol. 10, pp. 3121 - 3127 "The carotenois of blue-green algae".
  • Ref.364 : S. Takaichi, K. Shimada, and J. Ishidsu, Arch Microbiol.(1990) 153:118-122, "Carotenoids from the aerobic photosynthetic bacterium, Erythrobacter longus: β-Carotene and its hydroxyl derivatives".
  • CAS
    29307-44-6
    Links to other DB
    KEGG COMPOUND: C16284
    KNApSAcK: C00022921
    LipidBank: VCA1022
    ProCarDB: C1715

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