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Entry
CA00919                                                            

Classification
Carotenoid Name
Monoanhydrobacterioruberin;
MABR
IUPAC name 2-(3-Hydroxy-3-methylbutyl)-2'-(3-methylbut-2-enyl)-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-psi,psi-carotene-1,1'-diol
Formula
C50H74O3
Molecular Weight 
723.092 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/C50H74O3/c1-39(2)31-34-46(49(11,12)52)35-32-44(7)29-19-27-42(5)25-17-23-40(3)21-15-16-22-41(4)24-18-26-43(6)28-20-30-45(8)33-36-47(50(13,14)53)37-38-48(9,10)51/h15-33,35-36,46-47,51-53H,34,37-38H2,1-14H3/b16-15+,23-17+,24-18+,27-19+,28-20+,35-32+,36-33+,40-21+,41-22+,42-25+,43-26+,44-29+,45-30+
InChIKey
YZHIJCLHPFRXMT-KOJWWPMVSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C=C(\C=C\C(C(O)(C)C)CC=C(C)C)/C)/C)/C)/C=C/C=C(/C=C/C=C(/C=C/C(C(O)(C)C)CCC(O)(C)C)\C)\C
XLogP
14.547
Hydrogen Bond donors
(Lipinski's definition)
3
Hydrogen Bond Acceptors
(Lipinski's definition)
3
LipinskiFailures
2
Complexity of molecule
0.000
Number of heavy atoms
53
TPSA
(Topological Polar Surface Area) 
60.690 Å2
Source organisms
Halobacterium sp.  - Archaea: Euryarchaeota
Micrococcus roseus (Ref.387) - Actinobacteria
Haloarcula japonica (Ref.621) - Archaea: Euryarchaeota, triangular, disc-shaped, extremely halophilic archaeon that requires high concentrations of NaCl for growth
References
  • 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".
  • Ref.621 : Ying Yang, Rie Yatsunami, Ai Ando, Nobuhiro Miyoko, Toshiaki Fukui, Shinichi Takaichi, Satoshi Nakamura, "Complete Biosynthetic Pathway of the C50 Carotenoid Bacterioruberin from Lycopene in the Extremely Halophilic Archaeon Haloarcula japonica", Journal of Bacteriology, May 2015 Volume 197 Number 9.
  • CAS
    30403-58-8
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