Also known as: 303-33-3, 7s-heliotrine, (+)-heliotrine, Heliotron, Ccris 9196, Ai3-51769

Molecular Formula

C₁₆H₂₇NO₅

Molecular Weight

313.39 g/mol

InChI Key

LMFKRLGHEKVMNT-UJDVCPFMSA-N

FDA UNII

ZYB88Y4FUZ

heliotrine is a natural product found in Heliotropium arbainense, Heliotropium suaveolens, and other organisms with data available.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate

2.1.2 InChI

InChI=1S/C16H27NO5/c1-10(2)16(20,11(3)21-4)15(19)22-9-12-5-7-17-8-6-13(18)14(12)17/h5,10-11,13-14,18,20H,6-9H2,1-4H3/t11-,13+,14-,16+/m1/s1

2.1.3 InChI Key

LMFKRLGHEKVMNT-UJDVCPFMSA-N

2.1.4 Canonical SMILES

CC(C)C(C(C)OC)(C(=O)OCC1=CCN2C1C(CC2)O)O

2.1.5 Isomeric SMILES

C[C@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@H](CC2)O)O)OC

2.2 Other Identifiers

2.2.1 UNII

ZYB88Y4FUZ

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 303-33-3

2. 7s-heliotrine

3. (+)-heliotrine

4. Heliotron

5. Ccris 9196

6. Ai3-51769

7. Zyb88y4fuz

8. Chebi:5643

9. Butanoic Acid, 2-hydroxy-2-[(1r)-1-methoxyethyl]-3-methyl-, [(1s,7ar)-2,3,5,7a-tetrahydro-1-hydroxy-1h-pyrrolizin-7-yl]methyl Ester, (2s)-

10. Butanoic Acid, 2-hydroxy-2-((1r)-1-methoxyethyl)-3-methyl-, ((1s,7ar)-2,3,5,7a-tetrahydro-1-hydroxy-1h-pyrrolizin-7-yl)methyl Ester, (2s)-

11. ((1s,7ar)-1-hydroxy-2,3,5,7a-tetrahydro-1h-pyrrolizin-7-yl)methyl (2s,3r)-2-hydroxy-2-isopropyl-3-methoxybutanoate

12. Unii-zyb88y4fuz

13. Brn 0292841

14. 9-heliotrylheliotridine

15. Heliotrine, (+)-

16. Chembl2165593

17. Dtxsid3075381

18. Zinc488161

19. Mfcd00213991

20. Akos030495261

21. [(7s,8r)-7-hydroxy-5,6,7,8-tetrahydro-3h-pyrrolizin-1-yl]methyl (2s)-2-hydroxy-2-[(1r)-1-methoxyethyl]-3-methylbutanoate

22. Ai351769

23. Ai3 51769

24. Hy-126128

25. Cs-0090611

26. J-017913

27. Q27106845

28. (2s)-2-hydroxy-2-[(1r)-1-methoxyethyl]-3-methylbutanoic Acid [(1s,7ar)-2,3,5,7a-tetrahydro-1-hydroxy-1h-pyrrolizin-7-yl]methyl Ester

29. [(7s,8r)-7-hydroxy-5,6,7,8-tetrahydro-3h-pyrrolizin-1-yl]methyl (2s,3r)-2-hydroxy-2-isopropyl-3-methoxy-butanoate

30. [1s-[1alpha,7[r*(s*)],7aalpha]]-2-hydroxy-2-(1-methoxyethyl)-3-methylbutanoic Acid (2,3,5,7a-tetrahydro-1-hydroxy-1h-pyrrolizin-7-yl)methyl Ester

31. Butanoic Acid, 2-hydroxy-2-(1-methoxyethyl)-3-methyl-, (2,3,5,7a-tetrahydro-1-hydroxy-1h-pyrrolizin-7-yl)methyl Ester, (1s-(1 Alpha,7(2r*,3s*),7a Alpha))-

32. Butanoic Acid, 2-hydroxy-2-(1-methoxyethyl)-3-methyl-, (2,3,5,7a-tetrahydro-1-hydroxy-1h-pyrrolizin-7-yl)methyl Ester, (1s-(1.alpha.,7(r*(s*)),7a.alpha.))-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₂₇NO₅
Molecular Weight	313.39 g/mol
XLogP3	0.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	7
Exact Mass	313.18892296 g/mol
Monoisotopic Mass	313.18892296 g/mol
Topological Polar Surface Area	79.2 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	450
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

Heliotrine

Heliotrine

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