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Entry
CA00042                                                            

Classification
Carotenoid Name
3,4-Dehydrolycopene;
all-trans-3,4-Didehydrolycopene;
3,4-Didehydrolycopene
IUPAC name 3,4-Didehydro-psi,psi-carotene
Formula
C40H54
Molecular Weight 
534.832 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
13
Number of
conjugated multiple bonds 
13
Isomers 
  • Constitutional isomer: CA00196, CA00190, CA00307, CA00710, CA00315, CA00316, CA00588
  • InChI
    InChI=1S/C40H54/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-13,15-23,25-32H,14,24H2,1-10H3/b12-11+,23-13+,25-15+,26-16+,31-17+,32-18+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+
    InChIKey
    OCMSUPSDVXKDFY-FQMRBFJQSA-N
    Canonical SMILES
    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=C/C=C(/CCC=C(C)C)\C)\C
    XLogP
    14.544
    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
    40
    TPSA
    (Topological Polar Surface Area) 
    0.000 Å2
    Source organisms
    Staphylococcus aureus (Ref.540) - Firmicutes - Bacilli
    Rhodobacter azotoformans (Ref.111) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria
    Gibberella zeae (Ref.112) - Fungi: mold
    Neurospora crassa (Ref.113, Ref.117) - Fungi: mold
    Sitobion avenae (Ref.114) - Insect: aphid
    Helvella crispa (Ref.115) - Fungi: mushroom
    Helvella esculenta (Ref.115) - Fungi: mushroom
    Helvella gigas (Ref.115) - Fungi: mushroom
    Coccinella septempunctata (Ref.116) - Insect: seven-spotted ladybird
    Macrosiphum liriodendri (Ref.118) - Insect: aphid
    Myxococcus fulvus (Ref.119) - Deltaproteobacteria: halotolerant marine myxobacterium
    References
  • Ref.540 : Benjamin N. Mijts, Pyung Cheon Lee, Claudia Schmidt-Dannert, Chemistry & Biology, Volume 12, Issue 4, April 2005, Pages 453–460, "Identification of a Carotenoid Oxygenase Synthesizing Acyclic Xanthophylls: Combinatorial Biosynthesis and Directed Evolution".
  • Ref.111 : Zhang, Jinhua; Lu, Lili; Yin, Lijie; Xie, Shen; Xiao, Min, FEMS Microbiology Letters (2012), 333(2), 138-145., "Carotenogenesis gene cluster and phytoene desaturase catalyzing both three- and four-​step desaturations from Rhodobacter azotoformans".
  • Ref.112 : Jin, Jian-Ming; Lee, Jungkwan; Lee, Yin-Won, FEMS Microbiology Letters (2010), 302(2), 197-202., "Characterization of carotenoid biosynthetic genes in the ascomycete Gibberella zeae".
  • Ref.113 : Hausmann, Alexander; Sandmann, Gerhard, Fungal Genetics and Biology (2000), 30(2), 147-153., "A Single Five-​Step Desaturase Is Involved in the Carotenoid Biosynthesis Pathway to β-​Carotene and Torulene in Neurospora crassa".
  • Ref.117 : Goldie, A. Hughes; Subden, Ronald E., Biochemical Genetics (1973), 10(3), 275-84., "Neutral carotenoids of wild-​type and mutant strains of Neurospora crassa".
  • Ref.114 : Jenkins, R. L.; Loxdale, H. D.; Brookes, C. P.; Dixon, A. F. G., Physiological Entomology (1999), 24(2), 171-178., "The major carotenoid pigments of the grain aphid, Sitobion avenae (F.) (Hemiptera: Aphididae)".
  • Ref.115 : Czeczuga, B., Phyton (Horn, Austria) (1979), 19(3-4), 225-32., "Investigations on carotenoids in fungi. VI. Representatives of the Helvellaceae and Morchellaceae".
  • Ref.116 : Britton, George; Lockley, William J. S.; Harriman, Garry A.; Goodwin, Trevor W., Nature (London, United Kingdom) (1977), 266(5597), 49-50., "Pigmentation of the ladybird beetle Coccinella septempunctata by carotenoids not of plant origin".
  • Ref.118 : Andrewes, A. G.; Kjoesen, H.; Liaaen-Jensen, S.; Weisgraber, K. H.; Lousberg, R. J. J. C.; Weiss, U., Acta Chemica Scandinavica (1947-1973) (1971), 25(10), 3878-80., "Animal carotenoids. 7. Carotenes of two color variants of the aphid Macrosiphum liriodendri. Identification of natural γ,​γ-​carotene".
  • Ref.119 : Reichenbach, Hans; Kleinig, Hans, Archiv fuer Mikrobiologie (1971), 76(4), 364-80., "Carotenoids of myxobacteria. 4. Carotenoids of Myxococcus fulvus (myxobacterales)".
  • CAS
    7797-89-9
    Links to other DB
    KEGG COMPOUND: C15867
    KNApSAcK: C00022822
    LipidBank: VCA1005
    ProCarDB: C0663

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