Secoxyloganin

Synopsis, Chemistry

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Also known as: 58822-47-2, Secoxy-loganin, 65j8k23l9l, 2-[(2s,3r,4s)-3-ethenyl-5-methoxycarbonyl-2-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2h-pyran-4-yl]acetic acid, Unii-65j8k23l9l, Megxp0_000724

Molecular Formula

C₁₇H₂₄O₁₁

Molecular Weight

404.4 g/mol

InChI Key

MQLSOVRLZHTATK-PEYNGXJCSA-N

FDA UNII

65J8K23L9L

[(2S,3R,4S)-3-ethenyl-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]acetic acid is a natural product found in Lonicera japonica, Phillyrea latifolia, and other organisms with data available.

1 2D Structure

Secoxyloganin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]acetic acid

2.1.2 InChI

InChI=1S/C17H24O11/c1-3-7-8(4-11(19)20)9(15(24)25-2)6-26-16(7)28-17-14(23)13(22)12(21)10(5-18)27-17/h3,6-8,10,12-14,16-18,21-23H,1,4-5H2,2H3,(H,19,20)/t7-,8+,10-,12-,13+,14-,16+,17+/m1/s1

2.1.3 InChI Key

MQLSOVRLZHTATK-PEYNGXJCSA-N

2.1.4 Canonical SMILES

COC(=O)C1=COC(C(C1CC(=O)O)C=C)OC2C(C(C(C(O2)CO)O)O)O

2.1.5 Isomeric SMILES

COC(=O)C1=CO[C@H]([C@@H]([C@@H]1CC(=O)O)C=C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

2.2 Other Identifiers

2.2.1 UNII

65J8K23L9L

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Secoxy-loganin

2.3.2 Depositor-Supplied Synonyms

1. 58822-47-2

2. Secoxy-loganin

3. 65j8k23l9l

4. 2-[(2s,3r,4s)-3-ethenyl-5-methoxycarbonyl-2-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2h-pyran-4-yl]acetic Acid

5. Unii-65j8k23l9l

6. Megxp0_000724

7. Dtxsid90974342

8. Chebi:132712

9. Hy-n3009

10. Mfcd20260822

11. S9435

12. Zinc31157290

13. Akos032948707

14. Secologanoside 11-methyl Ester

15. Ccg-268689

16. Ncgc00380454-01

17. (2s-(2alpha,3beta,4beta))-3-ethenyl-2-(beta-d-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2h-pyran-4-acetic Acid

18. 2h-pyran-4-acetic Acid,3-ethenyl-2-(b-d-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-,(2s,3r,4s)-

19. Ac-34945

20. As-78339

21. Cs-0022922

22. [3-ethenyl-2-(hexopyranosyloxy)-5-(methoxycarbonyl)-3,4-dihydro-2h-pyran-4-yl]acetic Acid

23. (2s,3r,4s)-3-ethenyl-2-(.beta.-d-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2h-pyran-4-acetic Acid

24. (2s,3r,4s)-3-ethenyl-2-(beta-d-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2h-pyran-4-acetic Acid

25. [(2s,3r,4s)-3-ethenyl-2-(beta-d-glucopyranosyloxy)-5-(methoxycarbonyl)-3,4-dihydro-2h-pyran-4-yl]acetic Acid

26. 2-((2s,3r,4s)-5-(methoxycarbonyl)-2-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)-3-vinyl-3,4-dihydro-2h-pyran-4-yl)acetic Acid

27. 2h-pyran-4-acetic Acid, 3-ethenyl-2-(.beta.-d-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, (2s,3r,4s)-

28. 2h-pyran-4-acetic Acid, 3-ethenyl-2-(beta-d-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, (2s-(2alpha,3beta,4beta))-

29. Ncgc00380454-01_c17h24o11_2h-pyran-4-acetic Acid, 3-ethenyl-2-(beta-d-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, (2s,3r,4s)-

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₄O₁₁
Molecular Weight	404.4 g/mol
XLogP3	-1.6
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	8
Exact Mass	404.13186158 g/mol
Monoisotopic Mass	404.13186158 g/mol
Topological Polar Surface Area	172 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	618
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1