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Entry
CA00402                                                            

Classification
Carotenoid Name
β-Carotene diepoxide;
beta-Carotene diepoxide
IUPAC name (5R,6S,5'R,6'S)-5,6:5',6'-Diepoxy-5,6,5',6'-tetrahydro-beta,beta-carotene
Formula
C40H56O2
Molecular Weight 
568.848 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9
Number of
conjugated multiple bonds 
9
Isomers 
InChI
InChI=1S/C40H56O2/c1-31(19-13-21-33(3)23-29-39-35(5,6)25-15-27-37(39,9)41-39)17-11-12-18-32(2)20-14-22-34(4)24-30-40-36(7,8)26-16-28-38(40,10)42-40/h11-14,17-24,29-30H,15-16,25-28H2,1-10H3/b12-11+,19-13+,20-14+,29-23+,30-24+,31-17+,32-18+,33-21+,34-22+/t37-,38-,39+,40+/m1/s1
InChIKey
JMZDCQZKLCHTFI-HPLZOGFXSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\[C@]12O[C@]2(C)CCCC1(C)C)/C)/C)/C=C/C=C(/C=C/[C@]12O[C@]2(C)CCCC1(C)C)\C
XLogP
11.024
Hydrogen Bond donors
(Lipinski's definition)
0
Hydrogen Bond Acceptors
(Lipinski's definition)
2
LipinskiFailures
1
Complexity of molecule
0.327
Number of heavy atoms
42
TPSA
(Topological Polar Surface Area) 
25.060 Å2
Source organisms
Phaeophysica rubropulchra (Ref.280) - Fungi: lichen
Ipomoea batatas (Ref.291) - Land plant: sweet potato
Ipomoea batatas Lam. (Ref.295) - Land plant: sweet potato
References
  • Ref.280 : B. Czeczuga, Transactions of the Illinois State Academy of Science. {1992), "Carotenoids in Certain Lichens - in Illinois".
  • Ref.291 : Ligia Bicudo de Almeida1, Marilene De Vuono Camargo Penteado1, Kenneth L. Simpson2, George Britton, Murat Acemoglu, and Conrad Hans Eugster, Helvetica Chimica Acta Volume 69, Issue 7, pages 1554–1558, 29 October 1986, "Isolation and Characterisation of (5R, 6S,5'R,8'R)- and (5R,6S,5'R,8'S)-Luteochrome from Brazilian Sweet Potatoes (Ipomoea batatas LAM.)".
  • Ref.295 : Ligia B. Almeida, Marilene V.C. Penteado, Journal of Food Composition and Analysis, Volume 1, Issue 4, November 1988, Pages 341–352, "Carotenoids and pro-vitamin A value of white fleshed Brazilian sweet potatoes (Ipomoea batatas Lam.)".
  • CAS
    34222-90-7
    Links to other DB
    KNApSAcK: C00022952
    MassBank: CA000028

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