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Entry
CA00886                                                            
Classification
Carotenoid Name
Crocetindial;
Crocetin dialdehyde;
γ-crocetin;
gamma-crocetin
IUPAC name 8,8'-Diapocarotene-8,8'-dial
Formula
C20H24O2
Molecular Weight 
296.392 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9 including two aldehydes (9 in total)
Number of
conjugated multiple bonds 
9 including two aldehydes (9 in total)
Isomers 
InChI

InChIKey

Canonical SMILES

XLogP
4.634
Hydrogen Bond donors
(Lipinski's definition)
0
Hydrogen Bond Acceptors
(Lipinski's definition)
2
LipinskiFailures
0
Complexity of molecule
0.000
Number of heavy atoms
22
TPSA
(Topological Polar Surface Area) 
34.140 Å2
Reaction
  • Substrate: CR00176,  CR00213
  • Product: CR00038,  CR00056,  CR00070
    • Pathway
  • Pathway: CB000082,  CB000083
    • Major carotenoid information

    Minor carotenoid information

    Source organisms
    Synechocystis sp. PCC 6803 (Ref.147) - Cyanobacteria: freshwater cyanobacteria (Cyanobacteria - Merismopediaceae)
    Microcystis sp. (Ref.146) - Cyanobacteria (Cyanobacteria - Microcystaceae)
    Nostoc sp. PCC 7120 (Ref.550) - Cyanobacteria: same as Anabaena sp. PCC 7120 (Cyanobacteria - Nostocaceae)
    Crocus sativus (Ref.145) - Land plant: saffron crocus (Streptophyta - Iridaceae)
    Fusarium fujikuroi (Ref.555) - Fungi: ascomycete fungus (Ascomycota - Nectriaceae)
    References
  • Ref.145: Frusciante, Sarah; Diretto, Gianfranco; Bruno, Mark; Ferrante, Paola; Pietrella, Marco; Prado-Cabrero, Alfonso; Rubio-Moraga, Angela; Beyer, Peter; Gomez-Gomez, Lourdes; Al-Babili, Salim; et al, Proceedings of the National Academy of Sciences of the United States of America (2014), 111(33), 12246-12251., "Novel carotenoid cleavage dioxygenase catalyzes the first dedicated step in saffron crocin biosynthesis".
  • Ref.146: Harada, Ken-ichi; Hasegawa, Masateru; Fukushima, Naoko; Nishizawa, Akito; Fujise, Daiki; Tsuji, Kiyomi, Meijo Daigaku Sogo Kenkyusho Sogo Gakujutsu Kenkyu Ronbunshu (2010), 9, 83-91., "Degradation behavior of β-​carotene during cultivation of cyanobacteria".
  • Ref.147: Trautmann, Danika; Beyer, Peter; Al-Babili, Salim, FEBS Journal (2013), 280(15), 3685-3696., "The ORFslr0091 of Synechocystis sp. PCC6803 encodes a high-​light induced aldehyde dehydrogenase converting apocarotenals and alkanals".
  • Ref.550: Erin K. Marasco, Kimleng Vay, and Claudia Schmidt-Dannert, THE JOURNAL OF BIOLOGICAL CHEMISTRY VOL. 281, NO. 42, pp. 31583–31593, October 20, 2006, "Identification of Carotenoid Cleavage Dioxygenases from Nostoc sp. PCC 7120 with Different Cleavage Activities".
  • Ref.555: Alfonso Prado-Cabrero,Alejandro F. Estrada, Salim Al-Babili and Javier Avalos, Molecular Microbiology (2007) 64(2), 448–460, doi:10.1111/j.1365-2958.2007.05665.x, "Identification and biochemical characterization of anovel carotenoid oxygenase: elucidation of thecleavage step in theFusarium carotenoid pathway".
    • CAS
    502-70-5
    Links to other DB
    KNApSAcK: C00023152
    LipidBank: VCA1140

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