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Also known as: 6754-58-1, 569-83-5, Xantho-flav, 1-(2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one, (e)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one, T4467yt1nt

Molecular Formula

C₂₁H₂₂O₅

Molecular Weight

354.4 g/mol

InChI Key

ORXQGKIUCDPEAJ-YRNVUSSQSA-N

FDA UNII

T4467YT1NT

Xanthohumol is a prenylated flavonoid derived from the female flowers of the hops plant (Humulus lupulus L), with potential chemopreventive and antineoplastic activities. Upon administration, xanthohumol scavenges reactive oxygen species (ROS), thereby preventing DNA damage due to oxidative stress. In addition, xanthohumol is able to increase the expression of phase II cytoprotective enzymes, thereby inactivating carcinogens. This agent exerts anti-inflammatory activity, through the inhibition of inflammation-inducing enzymes, inhibits DNA synthesis, and induces apoptosis of susceptible cancer cells. Xanthohumol also decreases the expression of C-X-C chemokine receptor 4 (CXCR4), thereby preventing cancer cell invasion.

1 2D Structure

Xanthohumol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

2.1.2 InChI

InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+

2.1.3 InChI Key

ORXQGKIUCDPEAJ-YRNVUSSQSA-N

2.1.4 Canonical SMILES

CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)C=CC2=CC=C(C=C2)O)O)C

2.1.5 Isomeric SMILES

CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)/C=C/C2=CC=C(C=C2)O)O)C

2.2 Other Identifiers

2.2.1 UNII

T4467YT1NT

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (2e)-1-(2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one

2. (2e)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxy-3-(3-methyl-2-buten-1-yl)phenyl)-2-propen-1-one

3. 1-(2,4-dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one

4. 2,4,4',6-tetrahydroxy-3-(3,3-dimethylallyl)chalcone

5. Desmethylxanthohumol

6. Xantho-flav

7. Xanthoflav

2.3.2 Depositor-Supplied Synonyms

1. 6754-58-1

2. 569-83-5

3. Xantho-flav

4. 1-(2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

5. (e)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

6. T4467yt1nt

7. Chebi:66331

8. Xanthohumol(random Configuration)

9. 2',4,4'-trihydroxy-6'-methoxy-3'-prenylchalcone

10. 1-(2,4-dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one

11. (2e)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

12. (2e)-1-(2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one

13. (e)-1-(2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

14. (e)-1-(2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

15. 2-propen-1-one, 1-(2,4-hydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-, (e)-

16. Unii-t4467yt1nt

17. Mfcd00210576

18. (2e)-1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one

19. Xanthohumo

20. Xanthohumol From Hop (humulus Lupulus)

21. 2',4,4'-trihydroxy-3'-prenyl-6'-methoxychalcone

22. Xanthohumol [inci]

23. Schembl143683

24. Chembl253896

25. Megxp0_000104

26. Xanthohumol(randomconfiguration)

27. Acon1_001634

28. Chebi:94745

29. Dtxsid00893171

30. Hms3886h19

31. Bcp18498

32. Zinc5158937

33. Bdbm50384998

34. Lmpk12120294

35. S7889

36. Akos016010098

37. Ccg-268086

38. Db15359

39. (e)-1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)propenone

40. Smp2_000278

41. Ncgc00180304-01

42. Ac-31276

43. Bs-17392

44. X0068

45. A867246

46. Q408088

47. Brd-k77390737-001-01-6

48. Q27166535

49. Xanthohumol, Primary Pharmaceutical Reference Standard

50. Xanthohumol From Hop (humulus Lupulus), >=96% (hplc)

51. 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one

52. 2-propen-1-one, 1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-, (2e)-

2.4 Create Date

2006-01-18

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₂O₅
Molecular Weight	354.4 g/mol
XLogP3	5.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	6
Exact Mass	354.14672380 g/mol
Monoisotopic Mass	354.14672380 g/mol
Topological Polar Surface Area	87 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	515
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

Angiogenesis Inhibitors

Agents and endogenous substances that antagonize or inhibit the development of new blood vessels. (See all compounds classified as Angiogenesis Inhibitors.)

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