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Entry
CA00874                                                            

Classification
Carotenoid Name
Cochloxanthin
IUPAC name 6-Hydroxy-3-oxo-8'-apo-epsilon,psi-caroten-8'-oic acid
Formula
C30H38O4
Molecular Weight 
462.604 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9 and 2 including one carboxylic acid and one ketone (11 in total)
Number of
conjugated multiple bonds 
9 and 2 including one carboxylic acid and one ketone (11 in total)
Isomers 
InChI
InChI=1S/C30H38O4/c1-22(12-8-9-13-23(2)16-11-17-25(4)28(32)33)14-10-15-24(3)18-19-30(34)26(5)20-27(31)21-29(30,6)7/h8-20,34H,21H2,1-7H3,(H,32,33)/b9-8+,14-10+,16-11+,19-18+,22-12+,23-13+,24-15+,25-17+
InChIKey
GEXJMFRWDKABED-ILNMZGKRSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)O)/C)/C)/C=C/C=C(/C=C/C1(O)C(=CC(=O)CC1(C)C)C)\C
XLogP
6.007
Hydrogen Bond donors
(Lipinski's definition)
2
Hydrogen Bond Acceptors
(Lipinski's definition)
4
LipinskiFailures
1
Complexity of molecule
0.083
Number of heavy atoms
34
TPSA
(Topological Polar Surface Area) 
74.600 Å2
Source organisms
Cochlospermum tinctorium (Ref.376) - Land plant: Bixaceae
Cochlospermum vitifolium (Ref.377) - Land plant: Bixaceae: buttercup tree; wild cotton; forest peach; rose imperial
References
  • Ref.376 : Zederkopff Ballin, Nicolai; Traore, Maminata; Tinto, Halidou; Sittie, Archibald; Molgaard, Per; Olsen, Carl Erik; Kharazmi, Arsalan; Christensen, Soren Brogger, Journal of Natural Products (2002), 65(9), 1325-1327., "Antiplasmodial compounds from Cochlospermum tinctorium".
  • Ref.377 : Achenbach, Hans; Bluemm, Elmar; Waibel, Reiner, Tetrahedron Letters (1989), 30(23), 3059-60., "Vitixanthin and dihydrovitixanthin.  New unusual 7'-apocarotenoic acids from Cochlospermum vitifolium".
  • CAS
    109792-17-8
    Links to other DB
    KNApSAcK: C00023118

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