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Entry
CA00894                                                            

Classification
Carotenoid Name
Bixin;
cis-Bixin;
Bixinol;
alpha-Bixin
IUPAC name 6-Methyl hydrogen (9'Z)-6,6'-diapocarotene-6,6'-dioate
Formula
C25H30O4
Molecular Weight 
394.49 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Anticarcinogenic activity - inhibit tyrosinase activity in melanoma cells in vitro (Ref.481).
  • Number of
    conjugated double bonds 
    11 including one carboxylic acid and one carboxylic acid methyl ester (11 in total)
    Number of
    conjugated multiple bonds 
    11 including one carboxylic acid and one carboxylic acid methyl ester (11 in total)
    Isomers 
    InChI
    InChI=1S/C25H30O4/c1-20(12-8-14-22(3)16-18-24(26)27)10-6-7-11-21(2)13-9-15-23(4)17-19-25(28)29-5/h6-19H,1-5H3,(H,26,27)/b7-6+,12-8+,13-9+,18-16+,19-17+,20-10+,21-11+,22-14+,23-15-
    InChIKey
    RAFGELQLHMBRHD-SLEZCNMESA-N
    Canonical SMILES
    COC(=O)/C=C/C(=C\C=C\C(=C\C=C\C=C(\C=C\C=C(\C=C\C(=O)O)/C)/C)\C)/C
    XLogP
    6.603
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    29
    TPSA
    (Topological Polar Surface Area) 
    63.600 Å2
    Source organisms
    Bixa orellana (Ref.138, Ref.140) - Land plant: Bixaceae
    References
  • Ref.138 : Mercadante, A. Z.; Steck, A.; Pfander, H., Phytochemistry (1997), 46(8), 1379-1383., "Carotenoids from annatto. Part 3. Isolation and structure elucidation of minor carotenoids from annatto (Bixa orellana L.) seeds".
  • Ref.140 : Bouvier Florence; Dogbo Odette; Camara Bilal, Science (New York, N.Y.) (2003), 300(5628), 2089-91., "Biosynthesis of the food and cosmetic plant pigment bixin (annatto)".
  • Ref.481 : Anantharaman A, Hemachandran H, Priya RR, Sankari M, Gopalakrishnan M, Palanisami N, Siva R., J Biosci Bioeng. 2015 Jul 14. pii: S1389-1723(15)00200-5. doi: 10.1016/j.jbiosc.2015.05.007., PMID: 26187443, "Inhibitory effect of apocarotenoids on the activity of tyrosinase: Multi-spectroscopic and docking studies".
  • CAS
    6983-79-5
    Links to other DB
    KNApSAcK: C00003762
    LipidBank: VCA1128

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