Dihydroberberine

Synopsis, Chemistry

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Also known as: 483-15-8, Dihydroberbine, Dihydroumbellatine, 9,10-dimethoxy-6,8-dihydro-5h-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline, Lambertine, 7,8-dihydroberberine

Molecular Formula

C₂₀H₁₉NO₄

Molecular Weight

337.4 g/mol

InChI Key

FZAGOOYMTPGPGF-UHFFFAOYSA-N

16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0,.0,.0,]henicosa-1(21),2,4(8),9,15,17,19-heptaene is a natural product found in Thalictrum foliolosum, Berberis vulgaris, and Chelidonium majus with data available.

1 2D Structure

Dihydroberberine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,15(20),16,18-heptaene

2.1.2 InChI

InChI=1S/C20H19NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-9H,5-6,10-11H2,1-2H3

2.1.3 InChI Key

FZAGOOYMTPGPGF-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COC1=C(C2=C(C=C1)C=C3C4=CC5=C(C=C4CCN3C2)OCO5)OC

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Dihydroberberine Hydrochloride

2.2.2 Depositor-Supplied Synonyms

1. 483-15-8

2. Dihydroberbine

3. Dihydroumbellatine

4. 9,10-dimethoxy-6,8-dihydro-5h-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline

5. Lambertine

6. 7,8-dihydroberberine

7. Berberine, Dihydro-

8. 9,10-dimethoxy-2,3-(methylenedioxy)-13,13a-didehydroberbine

9. Dihydroberberine/dihydroumbellatine

10. Berbine, 13,13a-didehydro-9,10-dimethoxy-2,3-(methylenedioxy)-

11. 6h-benzo(g)-1,3-benzodioxolo(5,6-a)quinolizine, 5,8-dihydro-9,10-dimethoxy-

12. Nsc331264

13. 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,15(20),16,18-heptaene

14. 9,10-dimethoxy-5,8-dihydro-6h-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline

15. Nsc 331264

16. Brn 0344128

17. Lambertin

18. 3bti

19. 4-27-00-06505 (beilstein Handbook Reference)

20. Chembl11848

21. Schembl299738

22. Dtxsid70197476

23. Chebi:192073

24. Hy-n1934

25. Zinc1575028

26. Bdbm50480308

27. Mfcd00022312

28. Akos016010627

29. Nsc-331264

30. Ac-34205

31. Cs-0018246

32. Ft-0701465

33. A14704

34. A871933

35. 9,10-dimethoxy-2,3-(methylenedioxy)-13,13a-didehydrob

36. 9,10-dimethoxy-5,8-dihydro-6h-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline

37. 9,10-dimethoxy-5,8-dihydro-6h-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline #

38. 9,10-dimethoxy-6,8-dihydro-5h-1,3-dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline

39. 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2(10),3,8,15,17,19-heptaene

2.3 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₁₉NO₄
Molecular Weight	337.4 g/mol
XLogP3	3.5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	337.13140809 g/mol
Monoisotopic Mass	337.13140809 g/mol
Topological Polar Surface Area	40.2 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	538
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1