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Entry
CA00924                                                            

Classification
Carotenoid Name
Bacterioruberin monoglucoside
IUPAC name (2S,2'S)-2-(3-Glucosyloxy-3-methylbutyl)-2'-(3-hydroxy-3-methylbutyl)-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-psi,psi-carotene-1,1'-diol
Formula
C56H86O9
Molecular Weight 
903.248 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
13
Number of
conjugated multiple bonds 
13
Isomers 
InChI
InChI=1S/C56H86O9/c1-40(23-17-25-42(3)27-19-29-44(5)31-33-46(55(11,12)62)35-37-53(7,8)61)21-15-16-22-41(2)24-18-26-43(4)28-20-30-45(6)32-34-47(56(13,14)63)36-38-54(9,10)65-52-51(60)50(59)49(58)48(39-57)64-52/h15-34,46-52,57-63H,35-39H2,1-14H3/b16-15+,23-17+,24-18+,27-19+,28-20+,33-31+,34-32+,40-21+,41-22+,42-25+,43-26+,44-29+,45-30+/t46-,47-,48-,49-,50+,51-,52+/m1/s1
InChIKey
POVGDUDBCMCUCT-OITKYQALSA-N
Canonical SMILES
OC[C@H]1O[C@@H](OC(CC[C@H](C(O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C=C(/C=C/[C@@H](C(O)(C)C)CCC(O)(C)C)\C)\C)\C)/C)/C)/C)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
XLogP
12.542
Hydrogen Bond donors
(Lipinski's definition)
7
Hydrogen Bond Acceptors
(Lipinski's definition)
9
LipinskiFailures
3
Complexity of molecule
0.040
Number of heavy atoms
65
TPSA
(Topological Polar Surface Area) 
160.070 Å2
Source organisms
Halophilic bacterium strain BOS 66 (Ref.335) - Halophilic bacteria
Micrococcus roseus (Ref.387) - Actinobacteria
References
  • Ref.335 : Arpin, N.; Liaaen-Jensen, S.; Trouilloud, M., Acta Chemica Scandinavica, 26(1972), Pages: 2526-2528, "Bacterial Carotenoids. XXXIX. C5O-Carotenoids 10. Bacterioruberin Mono- and Diglucoside.".
  • Ref.387 : Strand, Aase; Shivaji, Sisinthy; Liaaen-Jensen, Synnove, Biochemical Systematics and Ecology (1997), 25(6), 547-552., "Bacterial carotenoids 55. C50-carotenoids 25. Revised structures of carotenoids associated with membranes in psychrotrophic Micrococcus roseus".
  • CAS
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