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Entry
CA00592                                                            

Classification
Carotenoid Name
Zeinoxanthin;
3-Hydroxy-alpha-carotene;
(3R,6'R)-beta,epsilon-Caroten-3-ol
IUPAC name (3R,6'R)-beta,epsilon-Caroten-3-ol
Formula
C40H56O
Molecular Weight 
552.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
10
Number of
conjugated multiple bonds 
10
Isomers 
InChI
InChI=1S/C40H56O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-14,16-26,36-37,41H,15,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+/t36-,37+/m1/s1
InChIKey
NBZANZVJRKXVBH-NHWXEJKLSA-N
Canonical SMILES
O[C@@H]1CC(=C(C(C1)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/[C@H]1C(=CCCC1(C)C)C)\C)\C)/C)/C)C
XLogP
13.102
Hydrogen Bond donors
(Lipinski's definition)
1
Hydrogen Bond Acceptors
(Lipinski's definition)
1
LipinskiFailures
1
Complexity of molecule
0.309
Number of heavy atoms
41
TPSA
(Topological Polar Surface Area) 
20.230 Å2
Source organisms
Prochlorococcus marinus strain CCMP 1986 (Ref.274) - Cyanobacteria
Prochlorococcus marinus strain CCMP 1375 (Ref.274) - Cyanobacteria
Acaryochloris marina strain MBIC 11017 (Ref.274) - Cyanobacteria: symbiotic species Unicellular Cyanobacterium, an epiphyte on red alga
Acaryochloris sp. strain Awaji (Ref.274) - Cyanobacteria: an epiphyte on red alga
References
  • Ref.274 : Shinichi Takaichi, Mari Mochimaru, Hiroko Uchida, Akio Murakami, Euichi Hirose, Takashi Maoka, Tohru Tsuchiya, and Mamoru Mimuro, Plant Cell Physiol. 53(11): 1881–1888 (2012) doi:10.1093/pcp/pcs126, "Opposite Chilarity of a-Carotene in Unusual Cyanobacteria with Unique Chlorophylls, Acaryochloris and Prochlorococcus".
  • CAS
    24480-38-4
    Links to other DB
    KEGG COMPOUND: C08590
    LipidBank: VCA1158

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