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Entry
CA00943                                                            

Classification
Carotenoid Name
Sarcinaxanthin monoglucoside
IUPAC name (2R,6R,2'R,6'R)-2-[4-(beta-D-Glucopyranosyloxy)-3-methylbut-2-enyl]-2'-(4-hydroxy-3-methylbut-2-enyl)-gamma,gamma-carotene
Formula
C56H82O7
Molecular Weight 
867.216 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9
Number of
conjugated multiple bonds 
9
Isomers 
InChI
InChI=1S/C56H82O7/c1-38(19-15-21-40(3)25-33-48-44(7)27-31-46(55(48,9)10)29-23-42(5)35-57)17-13-14-18-39(2)20-16-22-41(4)26-34-49-45(8)28-32-47(56(49,11)12)30-24-43(6)37-62-54-53(61)52(60)51(59)50(36-58)63-54/h13-26,33-34,46-54,57-61H,7-8,27-32,35-37H2,1-6,9-12H3/b14-13+,19-15+,20-16+,33-25+,34-26+,38-17+,39-18+,40-21+,41-22+,42-23+,43-24+/t46-,47-,48+,49+,50+,51+,52-,53+,54+/m0/s1
InChIKey
BRWOXKPPNFPCOO-KMXUZMIRSA-N
Canonical SMILES
OC/C(=C/C[C@H]1CCC(=C)[C@H](C1(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/[C@@H]1C(=C)CC[C@@H](C1(C)C)C/C=C(/CO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)\C)\C)\C)/C)/C)/C
XLogP
14.592
Hydrogen Bond donors
(Lipinski's definition)
5
Hydrogen Bond Acceptors
(Lipinski's definition)
7
LipinskiFailures
2
Complexity of molecule
0.283
Number of heavy atoms
63
TPSA
(Topological Polar Surface Area) 
119.610 Å2
Source organisms
Sarcina lutea (Ref.241) - Firmicutes - Clostridia
Micrococcus luteus (Ref.384) - Actinobacteria: normal inhabitant of human, same as Micrococcus lysodeikticus
Micrococcus yunnanensis (Ref.385) - Actinobacteria: isolated from surface-sterilized Polyspora axillaris roots
References
  • Ref.241 : Hertzberg, Sissel; Liaaen-Jensen, Synnoeve, Acta Chemica Scandinavica, Series B:  Organic Chemistry and Biochemistry (1977), 31(3), 215-18., "Bacterial carotenoids.  LIII.  C50-Carotenoids.  19.  Absolute configuration of sarcinaxanthin and sarcinaxanthin mono-β-D-glucoside.  Isolation of sarcinaxanthin diglycoside".
  • Ref.384 : Netzer, Roman; Brautaset, Trygve; Bruheim, Per, PCT Int. Appl. (2011), WO 2011151425 A1 20111208., "Discovery and cloning of a sarcinaxanthin biosynthesis gene cluster in Micrococcus luteus".
  • Ref.385 : Osawa, Ayako; Ishii, Yoko; Sasamura, Nao; Morita, Marie; Kasai, Hiroaki; Maoka, Takashi; Shindo, Kazutoshi, Journal of Oleo Science (2010), 59(12), 653-659., "Characterization and antioxidative activities of rare C50 carotenoids, sarcinaxanthin, sarcinaxanthin monoglucoside, and sarcinaxanthin diglucoside, obtained from Micrococcus yunnanensis".
  • CAS
    63545-53-9
    Links to other DB
    KNApSAcK: C00023087
    MassBank: CA000127

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