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Entry
CA00338                                                            

Classification
Carotenoid Name
Caloxanthin
IUPAC name (2R,3R,3'R)-beta,beta-Carotene-2,3,3'-triol
Formula
C40H56O3
Molecular Weight 
584.848 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/C40H56O3/c1-28(17-13-19-30(3)21-23-35-32(5)25-34(41)27-39(35,7)8)15-11-12-16-29(2)18-14-20-31(4)22-24-36-33(6)26-37(42)38(43)40(36,9)10/h11-24,34,37-38,41-43H,25-27H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,28-15+,29-16+,30-19+,31-20+/t34-,37-,38+/m1/s1
InChIKey
PKHJWTKRKQNNJE-RJLXQHJHSA-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](CC1(C)C)O)\C
XLogP
9.330
Hydrogen Bond donors
(Lipinski's definition)
3
Hydrogen Bond Acceptors
(Lipinski's definition)
3
LipinskiFailures
1
Complexity of molecule
0.303
Number of heavy atoms
43
TPSA
(Topological Polar Surface Area) 
60.690 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.6) - 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.6 : R. L. Smallidge and F. W. Quackenbush, Phytochemistry, 1973, Vol. 12, pp.2481 - 2482 (1973) "beta,beta-Carotene-2,3,3'-triol: a new carotenoid in Anacystis nidulans".
  • 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
    29267-88-7
    Links to other DB
    KEGG COMPOUND: C16282
    KNApSAcK: C00022906
    LipidBank: VCA1052
    ProCarDB: C1714

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