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Entry
CA00932                                                            

Classification
Carotenoid Name
C.p.450
IUPAC name (2R,2'R)-2,2'-Bis-(4-hydroxy-3-methylbut-2-enyl)-beta,beta-carotene
Formula
C50H72O2
Molecular Weight 
705.076 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
11
Number of
conjugated multiple bonds 
11
Isomers 
InChI
InChI=1S/C50H72O2/c1-37(19-15-21-39(3)25-33-47-43(7)27-31-45(49(47,9)10)29-23-41(5)35-51)17-13-14-18-38(2)20-16-22-40(4)26-34-48-44(8)28-32-46(50(48,11)12)30-24-42(6)36-52/h13-26,33-34,45-46,51-52H,27-32,35-36H2,1-12H3/b14-13+,19-15+,20-16+,33-25+,34-26+,37-17+,38-18+,39-21+,40-22+,41-23+,42-24+/t45-,46-/m0/s1
InChIKey
SVZOVYPHOOQVFZ-HXRVJUFCSA-N
Canonical SMILES
OC/C(=C/C[C@H]1CCC(=C(C1(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(C)CC[C@@H](C1(C)C)C/C=C(/CO)\C)\C)\C)/C)/C)C)/C
XLogP
14.704
Hydrogen Bond donors
(Lipinski's definition)
2
Hydrogen Bond Acceptors
(Lipinski's definition)
2
LipinskiFailures
2
Complexity of molecule
0.242
Number of heavy atoms
52
TPSA
(Topological Polar Surface Area) 
40.460 Å2
Source organisms
Corynebacterium glutamicum (Ref.190) - Actinobacteria: amino acid producing bacteria
Corynebacterium poinsettiae (Ref.386) - Actinobacteria
References
  • Ref.190 : Heider, Sabine A. E.; Peters-Wendisch, Petra; Netzer, Roman; Stafnes, Marit; Brautaset, Trygve; Wendisch, Volker F., Applied Microbiology and Biotechnology (2014), 98(3), 1223-1235., "Production and glucosylation of C50 and C40 carotenoids by metabolically engineered Corynebacterium glutamicum".
  • Ref.386 : Andrewes, Arthur G.; Liaaen-Jensen, Synnoeve, Tetrahedron Letters (1984), 25(11), 1191-4., "C50 carotenoids.  Part 21.  Revision of the structures of the bacterial C50-carotenoids C.p. 450 and C.p. 473".
  • CAS
    54783-71-0
    Links to other DB
    KNApSAcK: C00023081

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