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Chemistry

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Also known as: 480-41-1, Salipurpol, Salipurol, (s)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one, (s)-naringenin, Pelargidanon

Molecular Formula

C₁₅H₁₂O₅

Molecular Weight

272.25 g/mol

InChI Key

FTVWIRXFELQLPI-ZDUSSCGKSA-N

FDA UNII

HN5425SBF2

naringenin is a natural product found in Elaeodendron croceum, Garcinia multiflora, and other organisms with data available.

1 2D Structure

Naringenin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one

2.1.2 InChI

InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1

2.1.3 InChI Key

FTVWIRXFELQLPI-ZDUSSCGKSA-N

2.1.4 Canonical SMILES

C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O

2.1.5 Isomeric SMILES

C1[C@H](OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O

2.2 Other Identifiers

2.2.1 UNII

HN5425SBF2

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4',5,7-trihydroxyflavanone

2. Be 14348a

3. Be-14348a

4. Naringenin-7-sulfate

2.3.2 Depositor-Supplied Synonyms

1. 480-41-1

2. Salipurpol

3. Salipurol

4. (s)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one

5. (s)-naringenin

6. Pelargidanon

7. (2s)-naringenin

8. Naringetol

9. Naringenine

10. Asahina

11. Nsc 11855

12. Ccris 5839

13. (-)-naringenin

14. Yso1

15. Nsc 34875

16. (-)-(2s)-naringenin

17. Chembl9352

18. (s)-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-one

19. Ai3-23355

20. Hn5425sbf2

21. Chebi:17846

22. Flavanone, 4',5,7-trihydroxy-

23. 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-one

24. 4h-1-benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2s)-

25. Narigenin

26. Nsc-11855

27. (2s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4h-chromen-4-one

28. 5,7,4'-trihydroxyflavanone

29. (r,s)-naringenin

30. Sr-01000721771

31. (2s)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one

32. Unii-hn5425sbf2

33. 2uxu

34. 4deu

35. S-dihydrogenistein

36. Einecs 207-550-2

37. Pelargidanon 1602

38. Spectrum_000247

39. 4eh3

40. Naringenin [mi]

41. Spectrum2_000325

42. Spectrum3_000567

43. Spectrum4_000124

44. Spectrum5_001423

45. Naringenin [inci]

46. 4',5,7-trioh-flavone

47. 4',5,7-trihydroxyflavanon

48. Naringenin, (-)-

49. Schembl20570

50. Bspbio_001954

51. Kbiogr_000508

52. Kbioss_000727

53. Mls000574861

54. Bidd:er0116

55. Divk1c_000118

56. Spectrum1500746

57. Spbio_000329

58. 4',5, 7-trihydroxyflavanone

59. 5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4h-chromen-4-one

60. Dtxsid1022392

61. Bdbm23419

62. Hms500f20

63. Kbio1_000118

64. Kbio2_000727

65. Kbio2_003295

66. Kbio2_005863

67. Kbio3_001454

68. 4h-1-benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (s)-

69. Ninds_000118

70. (2s)-5,7,4'-trihydroxyflavone

71. Aids001417

72. Hms2202m06

73. Zinc156701

74. (2s)-4',5,7-trihydroxyflavanone

75. Hy-n0100

76. Tnp00287

77. (2s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one

78. (s)-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone

79. Ccg-38601

80. Lmpk12140001

81. Phytochemistry 8: 127 (1969)

82. S2394

83. (2s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-one

84. Akos016843490

85. Cs-6421

86. Db03467

87. Fs-4072

88. Sdccgmls-0066570.p001

89. (2s)-4',5,7-trihydroxyflavan-4-one

90. Idi1_000118

91. Ncgc00016457-01

92. Ncgc00016457-02

93. Ncgc00016457-03

94. Ncgc00017346-01

95. Ncgc00163598-01

96. Ac-33954

97. Cas-480-41-1

98. Flavanone, 4',5,7-trihydroxy- (8ci)

99. Smr000156272

100. Ft-0617134

101. Sw219329-1

102. C00509

103. A827427

104. Q418374

105. Q-100666

106. Sr-01000721771-3

107. Sr-01000721771-4

108. 5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chroman-4-one

109. Brd-k08832567-001-02-4

110. Brd-k08832567-001-06-5

111. (-)-(2s)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one

112. (s)-2,3-dihydo-5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-one

113. 2,3-dihydro-5,6-dihydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-one

114. 4h-1-benzopyran-4-one,2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2s)-

115. 13308-00-4

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₂O₅
Molecular Weight	272.25 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	1
Exact Mass	272.06847348 g/mol
Monoisotopic Mass	272.06847348 g/mol
Topological Polar Surface Area	87 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	363
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Estrogen Antagonists

Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds. (See all compounds classified as Estrogen Antagonists.)

Anti-Ulcer Agents

Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)

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