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Entry
CA01063                                                            

Classification
Carotenoid Name
(3S)-3-Hydroxycyclocitral;
3-OH-β-Cyclocitral;
3-OH-beta-Cyclocitral;
3-Hydroxy-beta-Cyclocitral
IUPAC name (3S)-3-Hydroxy-7-apo-beta-caroten-7-al
Formula
C10H16O2
Molecular Weight 
168.228 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • An aroma component of Asakusa-nori (Ref.623).
  • Number of
    conjugated double bonds 
    2 including one aldehyde (2 in total)
    Number of
    conjugated multiple bonds 
    2 including one aldehyde (2 in total)
    Isomers 
    InChI
    InChI=1S/C10H16O2/c1-7-4-8(12)5-10(2,3)9(7)6-11/h6,8,12H,4-5H2,1-3H3/t8-/m1/s1
    InChIKey
    SWPMTVXRLXPNDP-MRVPVSSYSA-N
    Canonical SMILES
    O=CC1=C(C)C[C@H](CC1(C)C)O
    XLogP
    0.901
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    0
    Complexity of molecule
    0.214
    Number of heavy atoms
    12
    TPSA
    (Topological Polar Surface Area) 
    37.300 Å2
    Source organisms
    Crocus sativus (Ref.454) - Land plant: saffron crocus
    Porphyra tenera (Ref.623) - Red alga: Bangiaceae, Asakusa-nori, same as Pyropia tenera
    References
  • Ref.454 : Sarah Frusciantea,b, Gianfranco Direttoa, Mark Brunoc, Paola Ferrantea, Marco Pietrellaa, Alfonso Prado-Cabrerod, Angela Rubio-Moragae, Peter Beyerc, Lourdes Gomez-Gomeze, Salim Al-Babilic,d, and Giovanni Giulianoa, PNAS, August 19, 2014, pp.12246–12251, vol. 111, no. 33, "Novel carotenoid cleavage dioxygenase catalyzes the first dedicated step in saffron crocin biosynthesis".
  • Ref.623 : Peter Winterhalter and Russell Rouseff, ”Carotenoid-Derived Aroma Compounds: An Introduction”, ACS Symposium Series; American Chemical Society: Washington, DC, 2001., doi: 10.1021/bk-2002-0802.ch001.
  • CAS

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