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Entry
CA00421                                                            

Classification
Carotenoid Name
Auroxanthin
IUPAC name (3S,5R,8RS,3'S,5'R,8'RS)-5,8:5',8'-Diepoxy-5,8,5',8'-tetrahydro-beta,beta-carotene-3,3'-diol
Formula
C40H56O4
Molecular Weight 
600.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
7
Number of
conjugated multiple bonds 
7
Isomers 
InChI
InChI=1S/C40H56O4/c1-27(17-13-19-29(3)33-21-35-37(5,6)23-31(41)25-39(35,9)43-33)15-11-12-16-28(2)18-14-20-30(4)34-22-36-38(7,8)24-32(42)26-40(36,10)44-34/h11-22,31-34,41-42H,23-26H2,1-10H3/b12-11+,17-13+,18-14+,27-15+,28-16+,29-19+,30-20+/t31-,32-,33?,34?,39+,40+/m0/s1
InChIKey
YLUSVJDFTAATNS-RFIAJWJGSA-N
Canonical SMILES
O[C@@H]1C[C@@]2(C)OC(C=C2C(C1)(C)C)/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C1C=C2[C@@](O1)(C)C[C@H](CC2(C)C)O)\C)\C)/C)/C
XLogP
6.456
Hydrogen Bond donors
(Lipinski's definition)
2
Hydrogen Bond Acceptors
(Lipinski's definition)
4
LipinskiFailures
1
Complexity of molecule
0.320
Number of heavy atoms
44
TPSA
(Topological Polar Surface Area) 
58.920 Å2
Source organisms
Chlorella pyrenoidosa (Ref.21) - Green alga: Trebouxiophyceae
Citrus sinensis L. Osbeck (Ref.373) - Land plant: orange
References
  • Ref.21 : B. Stephen Inbaraj, J.T. Chien, B. H. Chen. (2005); "Improved high performance liquid chromatographic method for determination of carotenoids in the microalga Chlorella pyrenoidosa".
  • Ref.373 : Kudritskaya, S. E.; Fishman, G. M.; Zagorodskaya, L. M., Subtropicheskie Kul'tury (1977), (5-6), 154-8., "Identification of orange peel (Citrus sinensis Osb.) carotenoids".
  • CAS
    27785-15-5
    Links to other DB
    MassBank: CA000005

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