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Entry
CA00944                                                            

Classification
Carotenoid Name
Sarcinaxanthin diglucoside
IUPAC name (2R,6R,2'R,6'R)-2,2'-Bis-[4-(beta-D-glucopyranosloxy)-3-methylbut-2-enyl]-gamma,gamma-carotene
Formula
C62H92O12
Molecular Weight 
1029.356 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/C62H92O12/c1-39(19-15-21-41(3)25-33-49-45(7)27-31-47(61(49,9)10)29-23-43(5)37-71-59-57(69)55(67)53(65)51(35-63)73-59)17-13-14-18-40(2)20-16-22-42(4)26-34-50-46(8)28-32-48(62(50,11)12)30-24-44(6)38-72-60-58(70)56(68)54(66)52(36-64)74-60/h13-26,33-34,47-60,63-70H,7-8,27-32,35-38H2,1-6,9-12H3/b14-13+,19-15+,20-16+,33-25+,34-26+,39-17+,40-18+,41-21+,42-22+,43-23+,44-24+/t47-,48-,49+,50+,51+,52+,53+,54+,55-,56-,57+,58+,59+,60+/m0/s1
InChIKey
TXDSGKKRBUEIDQ-QBWQXGLNSA-N
Canonical SMILES
OC[C@H]1O[C@@H](OC/C(=C/C[C@H]2CCC(=C)[C@H](C2(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/[C@@H]2C(=C)CC[C@@H](C2(C)C)C/C=C(/CO[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)\C)\C)\C)/C)/C)/C)[C@@H]([C@H]([C@@H]1O)O)O
XLogP
13.484
Hydrogen Bond donors
(Lipinski's definition)
8
Hydrogen Bond Acceptors
(Lipinski's definition)
12
LipinskiFailures
4
Complexity of molecule
0.313
Number of heavy atoms
74
TPSA
(Topological Polar Surface Area) 
198.760 Å2
Source organisms
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.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
    63566-61-0
    Links to other DB
    KNApSAcK: C00023088

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