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Entry
CA01030                                                            

Classification
Carotenoid Name
Tobiraxanthin D
IUPAC name (3S,3'S,5'R,6'S)-3,3',5',6'-tetrahydroxy-beta,beta-carotene-5,6-dione-3-myristate
Formula
C54H84O7
Molecular Weight 
845.212 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
10 including one ketone (10 in total)
Number of
conjugated multiple bonds 
10 including one ketone (10 in total)
Isomers 
InChI
InChI=1S/C54H84O7/c1-12-13-14-15-16-17-18-19-20-21-22-33-50(58)61-48(38-46(6)55)41-51(7,8)49(57)35-34-44(4)31-25-29-42(2)27-23-24-28-43(3)30-26-32-45(5)36-37-54(60)52(9,10)39-47(56)40-53(54,11)59/h23-32,34-37,47-48,56,59-60H,12-22,33,38-41H2,1-11H3/b24-23+,29-25+,30-26+,35-34+,37-36+,42-27+,43-28+,44-31+,45-32+/t47-,48+,53+,54+/m0/s1
InChIKey
QDZWWJNTPKQWQD-RIBAHGSFSA-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@@]1(O)C(C)(C)C[C@@H](C[C@@]1(C)O)O)\C)\C)/C)/C)(C)C)CC(=O)C
XLogP
14.363
Hydrogen Bond donors
(Lipinski's definition)
3
Hydrogen Bond Acceptors
(Lipinski's definition)
7
LipinskiFailures
2
Complexity of molecule
0.041
Number of heavy atoms
61
TPSA
(Topological Polar Surface Area) 
121.130 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
    229314-61-8
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