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Entry
CA00296                                                            

Classification
Carotenoid Name
Crassostreaxanthin A
IUPAC name (3R,3'R,5'R,6'S)-3',6'-Epoxy-3-hydroxy-6'-methyl-7,8-didehydro-1',2',5',6',7',8'-hexahydro-16'-nor-beta,psi-carotene-1',8'-dione
Formula
C40H54O4
Molecular Weight 
598.832 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
8 including one ketone (8 in total)
Number of
conjugated multiple bonds 
10 including one ketone (10 in total)
Isomers 
InChI
InChI=1S/C40H54O4/c1-28(17-13-18-30(3)21-22-37-32(5)23-35(42)26-39(37,8)9)15-11-12-16-29(2)19-14-20-31(4)38(43)27-40(10)33(6)24-36(44-40)25-34(7)41/h11-20,33,35-36,42H,23-27H2,1-10H3/b12-11+,17-13+,19-14+,28-15+,29-16+,30-18+,31-20+/t33-,35-,36-,40+/m1/s1
InChIKey
KFNGKYUGHHQDEE-AXWOCEAUSA-N
Canonical SMILES
O[C@@H]1CC(=C(C(C1)(C)C)C#C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C(=O)C[C@]1(C)O[C@H](C[C@H]1C)CC(=O)C)\C)\C)/C)/C)C
XLogP
8.485
Hydrogen Bond donors
(Lipinski's definition)
1
Hydrogen Bond Acceptors
(Lipinski's definition)
4
LipinskiFailures
2
Complexity of molecule
0.296
Number of heavy atoms
44
TPSA
(Topological Polar Surface Area) 
63.600 Å2
Source organisms
Crassostrea gigas (Ref.270) - Shellfish: pacific oyster
Corbicula japonica (Ref.221) - Shellfish: bivalve
Corbicula sandai (Ref.221) - Shellfish: bivalve
Corbicula clam (Ref.221) - Shellfish: bivalve
References
  • Ref.270 : Y Fujiwara, T Maoka, M Ookubo, T Matsuno - Tetrahedron letters, 1992, Volume 33, Issue 34, 18 August 1992, Pages 4941–4944 "Crassostreaxanthins A and B, novel marine carotenoids from the oyster Crassostrea gigas".
  • Ref.221 : Maoka, Takashi; Fujiwara, Yasuhiro; Hashimoto, Keiji; Akimoto, Naoshige, Journal of Agricultural and Food Chemistry (2005), 53(21), 8357-8364. "Carotenoids in Three Species of Corbicula Clams, Corbicula japonica, Corbicula sandai, and Corbicula sp. (Chinese Freshwater Corbicula Clam)".
  • CAS
    144615-56-5
    Links to other DB
    KNApSAcK: C00023166
    MassBank: CA000034

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