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Entry
CA00008                                                            

Classification
Carotenoid Name
4,4'-Diapophytoene;
(15Z)-4,4'-Diapophytoene;
Dehydrosqualene
IUPAC name 7,8,11,12,7',8',11',12'-Octahydro-4,4'-diapo-psi,psi-carotene
Formula
C30H48
Molecular Weight 
408.684 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
3
Number of
conjugated multiple bonds 
3
Isomers 
InChI
InChI=1S/C30H48/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h9-10,15-18,23-24H,11-14,19-22H2,1-8H3/b10-9-,27-17+,28-18+,29-23+,30-24+
InChIKey
NXJJBCPAGHGVJC-LIKFLUFESA-N
Canonical SMILES
C/C(=C\C=C/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)/CC/C=C(/CCC=C(C)C)\C
XLogP
11.110
Hydrogen Bond donors
(Lipinski's definition)
0
Hydrogen Bond Acceptors
(Lipinski's definition)
0
LipinskiFailures
2
Complexity of molecule
0.000
Number of heavy atoms
30
TPSA
(Topological Polar Surface Area) 
0.000 Å2
Source organisms
Streptococcus faecium UNH 564P (Ref.70) - Firmicutes - Bacilli
Staphylococcus aureus (Ref.192, Ref181) - Firmicutes - Bacilli
Sporosarcina aquimarina (Ref.77) - Firmicutes - Bacilli
Halobacillus halophilus (Ref.191) - Firmicutes - Bacilli
Heliobacillus mobilis (Ref.188) - Firmicutes - Clostridia
Heliophilum fasciatum (Ref.188) - Firmicutes - Clostridia
Heliobacterium chlorum (Ref.188) - Firmicutes - Clostridia
Heliobacterium modesticaldum (Ref.188) - Firmicutes - Clostridia
References
  • Ref.70 : Davies, Brian H.; Taylor, Richard F., Canadian Journal of Biochemistry (1982), 60(6), 684-92., "The biosynthesis of triterpenoid carotenoids in Streptococcus faecium UNH 564P".
  • Ref.192 : Pelz, Alexandra; Wieland, Karsten-Peter; Putzbach, Karsten; Hentschel, Petra; Albert, Klaus; Goetz, Friedrich, Journal of Biological Chemistry (2005), 280(37), 32493-32498., "Structure and Biosynthesis of Staphyloxanthin from Staphylococcus aureus".
  • Ref.77 : Steiger, Sabine; Perez-Fons, Laura; Fraser, Paul D.; Sandmann, Gerhard, Archives of Microbiology (2012), 194(9), 779-784., "The biosynthetic pathway to a novel derivative of 4,​4'-​diapolycopene-​4,​4'-​oate in a red strain of Sporosarcina aquimarina".
  • Ref.191 : Koecher, Saskia; Breitenbach, Juergen; Mueller, Volker; Sandmann, Gerhard, Archives of Microbiology (2009), 191(2), 95-104., "Structure, function and biosynthesis of carotenoids in the moderately halophilic bacterium Halobacillus halophilus".
  • Ref.188 : Takaichi, S., K. Inoue, M. Akaike, M. Kobayashi, H. Ohoka, and M. T. Madigan. 1997. The major carotenoid in all known species of heliobacteria is the C30 carotenoid 4,4-diaponeurosporene, not neurosporene. Arch. Microbiol. 168:277–281..
  • CAS
    53872-54-1
    Links to other DB
    KEGG COMPOUND: C16144
    KNApSAcK: C00000915
    LipidBank: VCA1049
    ProCarDB: C1837

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