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Chemistry

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Also known as: 22608-11-3, 24939-17-1, Curcumin ii, Monodemethoxycurcumin, Desmethoxycurcumin, Bhcfm

Molecular Formula

C₂₀H₁₈O₅

Molecular Weight

338.4 g/mol

InChI Key

HJTVQHVGMGKONQ-LUZURFALSA-N

FDA UNII

W2F8059T80

demethoxycurcumin is a natural product found in Curcuma amada, Curcuma aeruginosa, and other organisms with data available.

1 2D Structure

Demethoxycurcumin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione

2.1.2 InChI

InChI=1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+

2.1.3 InChI Key

HJTVQHVGMGKONQ-LUZURFALSA-N

2.1.4 Canonical SMILES

COC1=C(C=CC(=C1)C=CC(=O)CC(=O)C=CC2=CC=C(C=C2)O)O

2.1.5 Isomeric SMILES

COC1=C(C=CC(=C1)/C=C/C(=O)CC(=O)/C=C/C2=CC=C(C=C2)O)O

2.2 Other Identifiers

2.2.1 UNII

W2F8059T80

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-hydroxycinnamoyl(feroyl)methane

2. Curcumin Ii

3. Demethoxy-curcumin

4. Monodemethoxycurcumin

2.3.2 Depositor-Supplied Synonyms

1. 22608-11-3

2. 24939-17-1

3. Curcumin Ii

4. Monodemethoxycurcumin

5. Desmethoxycurcumin

6. Bhcfm

7. 4-hydroxycinnamoyl(feroyl)methane

8. Demethoxy Curcumin

9. 33171-16-3

10. (1e,6e)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione

11. Feruloyl-p-hydroxycinnnamoylmethane

12. Curcuminii

13. 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione

14. (2e)-demethoxy Curcumin

15. 1,6-heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-

16. P-hydroxycinnamoylferuloylmethane

17. Chebi:65737

18. 4-hydroxycinnamoyl(feruloyl)methane

19. Nsc687841

20. (1e,6e)-1-(4-hydroxy-3-methoxy-phenyl)-7-(4-hydroxyphenyl)hepta-1,6-di Ene-3,5-dione

21. W2f8059t80

22. (e/z)-demethoxycurcumin

23. Demethoxy-curcumin

24. (1e,6e)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione

25. (1e,6e)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-hepta-1,6-diene-3,5-dione

26. 1,6-heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-, (1e,6e)-

27. 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione

28. Unii-w2f8059t80

29. Mfcd03427310

30. Feruloyl-p-coumaroylmethane

31. (1e,6e)-demethoxycurcumin

32. (e,e)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione

33. Schembl431246

34. Chembl105360

35. Ins No.100(ii)

36. Schembl2553051

37. Demethoxycurcumin [inci]

38. Schembl13521973

39. Cid_5324476

40. Hy-n0006a

41. Ins-100(ii)

42. Dtxsid00873751

43. Desmethoxycurcumin [usp-rs]

44. Zinc5115722

45. Demethoxycurcumin, >=98% (hplc)

46. Bdbm50163744

47. E-100(ii)

48. S9280

49. Demethoxycurcumin, Analytical Standard

50. Akos015903509

51. Ccg-267896

52. Nsc-687841

53. Ac-34584

54. Bs-48948

55. Ls-14764

56. Cs-0009120

57. N1720

58. A14545

59. A910179

60. 6-bromo-2-pyridin-4-yl-quinoline-4-carboxylicacid

61. Q-100287

62. Q5264607

63. Desmethoxycurcumin (constituent Of Turmeric) [dsc]

64. 1-(4-hydroxystyryl)-3-(3-methoxy-4-hydroxystyryl)propanedial

65. (1e,6e)-1-(4-hydroxy-3-methoxy-phenyl)-7-(4-hydroxy-phenyl)-hepta-1,6-diene-3,5-dione

66. 1,6-heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)- (van)

67. 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, 9ci

68. 1-(4-hydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-hepta-1,6-diene-3,5-dione

69. 5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)hepta-1,4,6-trien-3-one

70. (1e,4z,6e)-5-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)-7-(4-hydroxy-phenyl)-hepta-1,4,6-trien-3-one

71. (1e,6e)-1-(4-hydroxy-3-methoxy-phenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₁₈O₅
Molecular Weight	338.4 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	7
Exact Mass	338.11542367 g/mol
Monoisotopic Mass	338.11542367 g/mol
Topological Polar Surface Area	83.8 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	502
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Metabolism/Metabolites

Demethoxycurcumin has known human metabolites that include Demethoxycurcumin O-glucuronide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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