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Entry
CA00459                                                            

Classification
Carotenoid Name
P457
IUPAC name (3S,5R,6S,3'S,5'R,6'R)-5,6-Epoxy-3',5'-dihydroxy-3-beta-lactosyloxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-beta,beta-caroten-20-al
Formula
C52H76O15
Molecular Weight 
941.128 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9 including one aldehyde (9 in total)
Number of
conjugated multiple bonds 
9 including one aldehyde (9 in total)
Isomers 
InChI
InChI=1S/C52H76O15/c1-31(15-12-16-32(2)20-21-39-48(4,5)24-35(56)25-50(39,8)62)14-10-11-18-34(28-53)19-13-17-33(3)22-23-52-49(6,7)26-36(27-51(52,9)67-52)63-46-44(61)42(59)45(38(30-55)65-46)66-47-43(60)41(58)40(57)37(29-54)64-47/h10-20,28,35-38,40-47,54-62H,22-27,29-30H2,1-9H3/b11-10+,15-12+,19-13+,31-14+,32-16+,33-17+,34-18+/t21-,35-,36-,37+,38+,40-,41-,42+,43+,44+,45+,46+,47+,50+,51+,52-/m0/s1
InChIKey
FKIHEGJMQUTCRD-BSEMLCGVSA-N
Canonical SMILES
O=C/C(=C/C=C/C=C(/C=C/C=C(/C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)O)\C)\C)/C=C/C=C(/CC[C@]12O[C@]2(C)C[C@H](CC1(C)C)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O)\C
XLogP
5.989
Hydrogen Bond donors
(Lipinski's definition)
9
Hydrogen Bond Acceptors
(Lipinski's definition)
15
LipinskiFailures
4
Complexity of molecule
0.315
Number of heavy atoms
67
TPSA
(Topological Polar Surface Area) 
248.590 Å2
Source organisms
Amphidinium carterae (Ref.33) - Alga: Dinoflagellate
Gymnodinum splendens (Ref.33) - Alga: Dinoflagellate
Gyrodinium dorsum (Ref.33) - Alga: Dinoflagellate
Symbiodinium sp. strain NBRC 104787 (Ref.277) - Alga: Dinoflagellate
References
  • Ref.33 : J. E. Joansen, W. A. Svec, and S. Liaaen-Jensen, Phytochemistry, 1974, Vol.13 pp.2261-2271, "Carotenoids of the Dinophyceae".
  • Ref.277 : Wakahama, Takahiro; Laza-Martinez, Aitor; Taha, Ahmad Iskandar Bin Haji Mohd; Okuyama, Hidetoshi; Yoshida, Kiyohito; Kogame, Kazuhiro; Awai, Koichiro; Kawachi, Masanobu; Maoka, Takashi; Takaichi, Shinichi, Journal of Phycology (2012), 48(6), 1392-1402., "Structural confirmation of a unique carotenoid lactoside, P457, in Symbiodinium sp. strain NBRC 104787 isolated from a sea anemone and its distribution in dinoflagellates and various marine organisms".
  • CAS
    55068-71-8
    Links to other DB
    KNApSAcK: C00022965

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