MolPort-001-742-487

Synopsis, Chemistry

ANALYTICAL SOLUTION(s)

2 Other Ref. Standards

2 Other Ref. Standards

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Also known as: 479-98-1, Aucuboside, Rhinanthin, 2g52gs8uml, Rhimantin, Chebi:69796

Molecular Formula

C₁₅H₂₂O₉

Molecular Weight

346.33 g/mol

InChI Key

RJWJHRPNHPHBRN-FKVJWERZSA-N

FDA UNII

2G52GS8UML

aucubin is a natural product found in Verbascum lychnitis, Plantago media, and other organisms with data available.

1 2D Structure

MolPort-001-742-487

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3R,4S,5S,6R)-2-[[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

2.1.2 InChI

InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/m0/s1

2.1.3 InChI Key

RJWJHRPNHPHBRN-FKVJWERZSA-N

2.1.4 Canonical SMILES

C1=COC(C2C1C(C=C2CO)O)OC3C(C(C(C(O3)CO)O)O)O

2.1.5 Isomeric SMILES

C1=CO[C@H]([C@H]2[C@@H]1[C@@H](C=C2CO)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O

2.2 Other Identifiers

2.2.1 UNII

2G52GS8UML

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Aucubuside

2.3.2 Depositor-Supplied Synonyms

1. 479-98-1

2. Aucuboside

3. Rhinanthin

4. 2g52gs8uml

5. Rhimantin

6. Chebi:69796

7. (1s,4ar,5s,7as)-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl Beta-d-glucopyranoside

8. Einecs 207-540-8

9. Unii-2g52gs8uml

10. Nsc 407293

11. Nsc-407293

12. (2s,3r,4s,5s,6r)-2-[[(1s,4ar,5s,7as)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

13. Mfcd00136026

14. Aucubin [mi]

15. Aucubin, Analytical Standard

16. 1,4a,5,7a-tetrahydro-5-hydroxy-7-hydroxymethylcyclopenta(c)pyran-1-yl-beta-d-glucopyranoside

17. Mls002473252

18. Schembl381032

19. Chembl514882

20. Megxp0_001729

21. Acon1_002452

22. Dtxsid60963965

23. Hms3098b08

24. Hy-n0664

25. Zinc4098334

26. S5459

27. Akos015896774

28. Ccg-267985

29. Cs-5367

30. Lmpr0102070006

31. Ncgc00169833-01

32. Ncgc00169833-02

33. (1s-(1alpha,4aalpha,5alpha,7aalpha))-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta(c)pyran-1-yl-beta-d-glucopyranoside

34. (2s,3r,4s,5s,6r)-2-(((1s,4ar,5s,7as)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl)oxy)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol

35. (2s,3r,4s,5s,6r)-2-[[(1s,4ar,5s,7as)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

36. Ac-33938

37. As-74899

38. Smr001397339

39. N2758

40. C09771

41. 479a981

42. A827419

43. Aucubin, Primary Pharmaceutical Reference Standard

44. Q418014

45. Aucubin (constituent Of Chaste Tree) [dsc]

46. Q-100516

47. (1s,4ar,5s,7as)-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta(c)pyran-1-yl-.beta.-d-glucopyranoside

48. (2s,3r,4s,5s,6r)-2-((1s,4ar,5r,7as)-5-hydroxy-7-hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-1-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

49. (2s,3r,4s,5s,6r)-2-((1s,4ar,5s,7as)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yloxy)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol

50. (2s,3r,4s,5s,6r)-2-{[(1s,4ar,5s,7as)-5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

51. .beta.-d-glucopyranoside, (1s,4ar,5s,7as)-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl

52. B-d-glucopyranoside, (1s,4ar,5s,7as)-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₂₂O₉
Molecular Weight	346.33 g/mol
XLogP3	-3
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	4
Exact Mass	346.12638228 g/mol
Monoisotopic Mass	346.12638228 g/mol
Topological Polar Surface Area	149 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	507
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1