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Entry
CA01027                                                            

Classification
Carotenoid Name
Tobiraxanthin A3
IUPAC name (3S,3'S)-3,3'-dihydroxy-5,6,5',6'-diseco-beta,beta-carotene-5,6,5',6'-tetraone-dilaurate
Formula
C64H100O8
Molecular Weight 
997.44 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/C64H100O8/c1-13-15-17-19-21-23-25-27-29-41-61(69)71-57(47-55(7)65)49-63(9,10)59(67)45-43-53(5)39-33-37-51(3)35-31-32-36-52(4)38-34-40-54(6)44-46-60(68)64(11,12)50-58(48-56(8)66)72-62(70)42-30-28-26-24-22-20-18-16-14-2/h31-40,43-46,57-58H,13-30,41-42,47-50H2,1-12H3/b32-31+,37-33+,38-34+,45-43+,46-44+,51-35+,52-36+,53-39+,54-40+/t57-,58-/m1/s1
InChIKey
YBROMIZOJXNWSO-RCKPQAPXSA-N
Canonical SMILES
CCCCCCCCCCCC(=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)CCCCCCCCCCC)CC(=O)C)(C)C)\C)\C)/C)/C)(C)C)CC(=O)C
XLogP
18.664
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
72
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
    229314-58-3
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