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Entry
CA00288                                                            

Classification
Carotenoid Name
Neurosporaxanthin methyl ester
IUPAC name Methyl 4'-apo-beta,psi-caroten-4'-oate
Formula
C36H48O2
Molecular Weight 
512.744 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
12 including one carboxylic acid methyl ester (12 in total)
Number of
conjugated multiple bonds 
12 including one carboxylic acid methyl ester (12 in total)
Isomers 
InChI
InChI=1S/C36H48O2/c1-28(18-12-20-30(3)22-14-23-33(6)35(37)38-9)16-10-11-17-29(2)19-13-21-31(4)25-26-34-32(5)24-15-27-36(34,7)8/h10-14,16-23,25-26H,15,24,27H2,1-9H3/b11-10+,18-12+,19-13+,22-14+,26-25+,28-16+,29-17+,30-20+,31-21+,33-23+
InChIKey
CXZXVEIFQBEHTM-HHOXJLNZSA-N
Canonical SMILES
COC(=O)/C(=C/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C)/C)/C)/C
XLogP
11.704
Hydrogen Bond donors
(Lipinski's definition)
0
Hydrogen Bond Acceptors
(Lipinski's definition)
2
LipinskiFailures
2
Complexity of molecule
0.070
Number of heavy atoms
38
TPSA
(Topological Polar Surface Area) 
26.300 Å2
Source organisms
Verticillium agaricinum (Ref.299) - Fungi: mold
Nectria cinnabarina (Ref.300) - Fungi: mold
References
  • Ref.299 : Valadon, L. R. G.; Mummery, Rosemary S., Phytochemistry (Elsevier) (1977), 16(5), 613-14., "Natural β-apo-4'-carotenoic acid methyl ester in the fungus Verticillium agaricinum".
  • Ref.300 : Fiasson, Jean L.; Bouchez, Marie P., Fiasson, Jean L.; Bouchez, Marie P., "Chemotaxonomy of fungi.  XIII.  Presence of neurosporaxanthine methyl ester in the ascomycete, Nectria cinnabarina".
  • CAS
    5389-78-6
    Links to other DB
    KNApSAcK: C00023103

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