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Entry
CA00348                                                            

Classification
Carotenoid Name
Heteroxanthin
IUPAC name (3S,5S,6S,3'R)-7',8'-didehydro-5,6-dihydro-beta,beta-carotene-3,5,3',6'-tetrol
Formula
C40H56O4
Molecular Weight 
600.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
8
Number of
conjugated multiple bonds 
10
Isomers 
InChI
InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40(44)38(8,9)27-35(42)28-39(40,10)43/h11-20,23-24,34-35,41-44H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,24-23+,29-15+,30-16+,31-19+,32-20+/t34-,35+,39+,40+/m1/s1
InChIKey
ZEXQVPRPMQVOFT-PZRZDZAUSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C#CC1=C(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/[C@]1(O)C(C)(C)C[C@@H](C[C@]1(C)O)O)\C
XLogP
9.141
Hydrogen Bond donors
(Lipinski's definition)
4
Hydrogen Bond Acceptors
(Lipinski's definition)
4
LipinskiFailures
1
Complexity of molecule
0.300
Number of heavy atoms
44
TPSA
(Topological Polar Surface Area) 
80.920 Å2
Source organisms
Gonyostomum semen (Ref.35) - Alga: Raphidophyceae
Vacuolaria virescens (Ref.35) - Alga: Raphidophyceae
Euglena gracilis (Ref.39, Ref.590) - Alga: Euglenoid
Euglena viridis (Ref.44) - Alga: Euglenoid
Corbicula japonica (Ref.221) - Shellfish: bivalve
Corbicula sandai (Ref.221) - Shellfish: bivalve
Corbicula clam (Ref.221) - Shellfish: bivalve
References
  • Ref.35 : A.Fiksdahl, N. Withers, R. R. L. Guillard, and S. Liaaen-Jensen, Comp. Biochem. Physiol. Vol. 78B, No. 1, pp. 265-271, 1984, "Carotenoids of the Raphidophyceae - a chemosystematic contribution ".
  • Ref.39 : H. Nitsche, Arch. Mikrobiol. 90, 151-155 (1973), "Heteroxanthin in Euglena gracilis".
  • Ref.590 : Richard Buchecker, Synnøve Liaaen-Jensen, Phytochemistry, Volume 16, Issue 6, 1977, Pages 729-733, "Absolute configuration of heteroxanthin and diadinoxanthin".
  • Ref.44 : A. Fiksdahl, S. Liaaen-Jensen, Phytochemistry, Vol.27, No.5, pp. 1447 - 1450, 1988 "Diacetylenic carotenoids from Euglena viridis".
  • 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
    29488-00-4
    Links to other DB
    KNApSAcK: C00022925
    MassBank: CA000062

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