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Entry
CA01160                                                            

Classification
Carotenoid Name
Carlactonoic acid;
CLA
IUPAC name (E,2Z)-6,6-dimethyl-2-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylidene]-5-propan-2-ylideneoct-3-enoic acid;
10-apo-beta-caroten-19-oic acid-10-(hydroxy-methyl-furanone) (defined by Carotenoids DB)
Formula
C19H24O5
Molecular Weight 
316.382 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
4 including one carboxylic acid and 2 including one ketone (6 in total)
Number of
conjugated multiple bonds 
4 including one carboxylic acid and 2 including one ketone (6 in total)
Isomers 
InChI
InChI=1S/C19H24O5/c1-12-6-5-9-19(3,4)15(12)8-7-14(17(20)21)11-23-16-10-13(2)18(22)24-16/h7-8,10-11,16H,5-6,9H2,1-4H3,(H,20,21)/b8-7+,14-11+
InChIKey
WUBRWXCVIPHXLX-DQBULIGTSA-N
Canonical SMILES
OC(=O)/C(=C/OC1OC(=O)C(=C1)C)/C=C/C1=C(C)CCCC1(C)C
XLogP
4.535
Hydrogen Bond donors
(Lipinski's definition)
1
Hydrogen Bond Acceptors
(Lipinski's definition)
5
LipinskiFailures
0
Complexity of molecule
0.333
Number of heavy atoms
24
TPSA
(Topological Polar Surface Area) 
72.830 Å2
Source organisms
Arabidopsis sp. (Ref.619) - 
References
  • Ref.619 : Abe S., Sado A., Tanaka K., Kisugi T., Asami K., Ota S., Kim H. II., Yoneyama K., Xiaonan Xie, Ohnishi T., Seto Y., Yamaguchi S., Akiyama K., Yoneyama K., Nomura T. (2014), Carlactone is converted to carlactonoic acid by MAX1 in Arabidopsis and its methyl ester can directly interact with AtD14 in vitro, PNAS, December 16, 2014, vol. 111, no. 50, pp.18084–18089, www.pnas.org/cgi/doi/10.1073/pnas.1410801111.
  • CAS

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