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Entry
CA01025                                                            

Classification
Carotenoid Name
Tobiraxanthin A1
IUPAC name (3S,3'S)-3,3'-dihydroxy-5,6,5',6'-diseco-beta,beta-carotene-5,6,5',6'-tetraone-dimyristate
Formula
C68H108O8
Molecular Weight 
1053.544 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
11 including two ketones (11 in total)
Number of
conjugated multiple bonds 
11 including two ketones (11 in total)
Isomers 
InChI
InChI=1S/C68H108O8/c1-13-15-17-19-21-23-25-27-29-31-33-45-65(73)75-61(51-59(7)69)53-67(9,10)63(71)49-47-57(5)43-37-41-55(3)39-35-36-40-56(4)42-38-44-58(6)48-50-64(72)68(11,12)54-62(52-60(8)70)76-66(74)46-34-32-30-28-26-24-22-20-18-16-14-2/h35-44,47-50,61-62H,13-34,45-46,51-54H2,1-12H3/b36-35+,41-37+,42-38+,49-47+,50-48+,55-39+,56-40+,57-43+,58-44+/t61-,62-/m1/s1
InChIKey
GLZKMOHEXKQACW-YCWVDWBYSA-N
Canonical SMILES
CCCCCCCCCCCCCC(=O)O[C@@H](CC(C(=O)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C(=O)C(C[C@H](OC(=O)CCCCCCCCCCCCC)CC(=O)C)(C)C)\C)\C)/C)/C)(C)C)CC(=O)C
XLogP
20.940
Hydrogen Bond donors
(Lipinski's definition)
0
Hydrogen Bond Acceptors
(Lipinski's definition)
8
LipinskiFailures
2
Complexity of molecule
0.000
Number of heavy atoms
76
TPSA
(Topological Polar Surface Area) 
120.880 Å2
Source organisms
Pittosporum tobira (Ref.403, Ref.404, Ref.405) - Land plant
References
  • Ref.403 : Maoka, Takashi; Hashimoto, Keiji; Manabe, Kiyoshi; Fujiwara, Yasuhiro, Tennen Yuki Kagobutsu Toronkai Koen Yoshishu (1997), 39th, 487-492., "Structures of novel red carotenoids, tobiraxanthins from the seeds of Pittosporum tobira".
  • Ref.404 : Fujiwara, Yasuhiro; Hashimoto, Keiji; Manabe, Kiyoshi; Maoka, Takashi, Tetrahedron Letters (2002), 43(24), 4385-4388., "Structures of tobiraxanthins A1, A2, A3, B, C and D, new carotenoids from the seeds of Pittosporum tobira".
  • Ref.405 : Maoka, Takashi; Fujiwara, Yasuhiro; Hashimoto, Keiji; Akimoto, Naoshige, Phytochemistry (Elsevier) (2006), 67(19), 2120-2125., "5-Hydroxy-seco-carotenoids from Pittosporum tobira".
  • CAS
    229314-56-1
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