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Entry
CA00539                                                            

Classification
Carotenoid Name
Fucoxanthin pyropheophorbide A ester
IUPAC name (3S,5R,6S,3'S,5'R,6'R)-3'-[(3S,4S)-9-ethenyl-14-ethyl-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoate]-5,6-Epoxy-3'-ethanoyloxy-3,5'-dihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-beta,beta-caroten-8-one
Formula
C75H90N4O8
Molecular Weight 
1175.51 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9 and 12 including one ketone (21 in total)
Number of
conjugated multiple bonds 
9 and 12 (21 in total)
Isomers 
InChI
InChI=1S/C75H90N4O8/c1-18-54-47(7)58-35-60-49(9)56(69(78-60)57-34-64(81)68-50(10)61(79-70(57)68)37-63-55(19-2)48(8)59(77-63)36-62(54)76-58)31-33-67(83)86-53-39-72(14,15)75(74(17,41-53)87-75)42-65(82)46(6)29-23-28-44(4)25-21-20-24-43(3)26-22-27-45(5)30-32-66-71(12,13)38-52(85-51(11)80)40-73(66,16)84/h18,20-30,35-37,49,52-53,56,76,79,84H,1,19,31,33-34,38-42H2,2-17H3/b21-20+,26-22+,28-23+,43-24+,44-25+,45-27+,46-29+,58-35-,59-36-,60-35-,61-37-,62-36-,63-37-,69-57-/t32-,49-,52-,53-,56-,73+,74+,75-/m0/s1
InChIKey
IVBGVRUUVNIYEJ-ABNJTJASSA-N
Canonical SMILES
CCC1=C(C)C2=N/C/1=C\c1[nH]c3c(c1C)C(=O)C/C/3=C\1/N=C(/C=c/3\[nH]/c(=C\2)/c(C=C)c3C)[C@H]([C@@H]1CCC(=O)O[C@H]1CC(C)(C)[C@]2([C@](C1)(C)O2)CC(=O)/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)OC(=O)C)\C)\C)/C)/C)C
XLogP
15.563
Hydrogen Bond donors
(Lipinski's definition)
3
Hydrogen Bond Acceptors
(Lipinski's definition)
12
LipinskiFailures
3
Complexity of molecule
0.345
Number of heavy atoms
87
TPSA
(Topological Polar Surface Area) 
176.860 Å2
Source organisms
Haliotis diversicolor aquatilis (Ref.157) - Shellfish: Abalone
References
  • Ref.157 : Maoka, Takashi; Etoh, Tetsuji; Akimoto, Naoshige; Yasui, Hiroyuki, Tetrahedron Letters (2011), Volume52 Issue23 Pages3012-3015, DOI:10.1016/j.tetlet.2011.03.14, "Novel carotenoid pyropheophorbide A esters from abalone".
  • CAS
    171882-97-6
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