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Also known as: 10236-47-2, Naringoside, Aurantiin, Naringenin 7-o-neohesperidoside, 4'5-dioh-flavone-7-rhgluc, Chembl451532

Molecular Formula

C₂₇H₃₂O₁₄

Molecular Weight

580.5 g/mol

InChI Key

DFPMSGMNTNDNHN-ZPHOTFPESA-N

FDA UNII

N7TD9J649B

naringin is a natural product found in Podocarpus fasciculus, Citrus latipes, and other organisms with data available.

1 2D Structure

Naringin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one

2.1.2 InChI

InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

2.1.3 InChI Key

DFPMSGMNTNDNHN-ZPHOTFPESA-N

2.1.4 Canonical SMILES

CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O

2.1.5 Isomeric SMILES

C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

N7TD9J649B

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4',5,7-trihydroxyflavanone 7-rhamnoglucoside

2. Aurantiin

3. Cyclorel

4. Naringenin-7-hesperidoside

5. Naringin Dihydrochalcone

6. Naringin Sodium

2.3.2 Depositor-Supplied Synonyms

1. 10236-47-2

2. Naringoside

3. Aurantiin

4. Naringenin 7-o-neohesperidoside

5. 4'5-dioh-flavone-7-rhgluc

6. Chembl451532

7. N7td9j649b

8. (2s)-7-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one

9. Chebi:28819

10. Naringenin 7-rhamnoglucoside

11. (s)-7-(((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)tetrahydro-2h-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one

12. 7-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one

13. Naringenin 7-o-[alpha-l-rhamnosyl-(1->2)-beta-d-glucoside]

14. Mfcd00148888

15. (2s)-naringin

16. Naringenine-7-rhamnosidoglucoside

17. Sr-01000736681

18. Unii-n7td9j649b

19. Naringenin,(s)

20. Naringenin-7-beta-neohesperidoside

21. (s)-7-((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)tetrahydro-2h-pyran-2-yloxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one

22. Einecs 233-566-4

23. Naringin (naringoside)

24. Naringin [inci]

25. Ai3-19008

26. Naringin [mi]

27. 132203-74-8

28. Prestwick0_000467

29. Prestwick1_000467

30. Prestwick2_000467

31. Prestwick3_000467

32. Naringin [usp-rs]

33. Aurantiin [who-dd]

34. Schembl23432

35. Bspbio_000574

36. Cid_25075

37. Mls000069459

38. Bidd:er0262

39. Divk1c_000247

40. Spbio_002513

41. Bpbio1_000632

42. Cid_442428

43. Gtpl4738

44. Megxp0_001877

45. Naringin Extract [fhfi]

46. Dtxsid6022478

47. Acon1_000139

48. Hms500m09

49. Kbio1_000247

50. Ninds_000247

51. Citrus Naringinine [vandf]

52. Hms2231m18

53. Hy-n0153

54. Zinc8143604

55. Bdbm50241582

56. S2329

57. Akos016034302

58. Ccg-208591

59. Cs-5632

60. Idi1_000247

61. Ncgc00142617-01

62. Ncgc00142617-02

63. Ncgc00142617-03

64. 5-hydroxy-2-(4-hydroxyphenyl)-7-(2-o-alpha-l-rhamnopyranosyl-beta-d-glucopyranosyloxy)-4-chromanon

65. 7-(2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavone

66. As-12929

67. Smr000059108

68. Xn167836

69. N2371

70. 4',5,7-trihydroxyflavanone-7-rhamnoglucoside

71. C09789

72. 236n472

73. A800566

74. Q418469

75. Sr-01000736681-4

76. Sr-01000736681-5

77. Brd-k02953697-001-09-2

78. Brd-k02953697-002-03-3

79. Naringenin 7-o-alpha-l-rhamnosyl-(1->2)-beta-d-glucoside

80. Naringenin 7-o-(alpha-l-rhamnosyl-(1,2)-beta-d-glucoside)

81. (2s)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2h-chromen-7-yl 2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranoside

82. (2s)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2h-chromen-7-yl 2-o-(6-deoxy-alpha-l-mannopyranosyl)-betad-glucopyranoside

83. (2s)-7-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one

84. (2s)-7-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one

85. (2s)-7-[(2s,4s,5s,3r,6r)-3-((2s,6s,3r,4r,5r)-3,4,5-trihydroxy-6-methyl(2h-3,4, 5,6-tetrahydropyran-2-yloxy))-4,5-dihydroxy-6-(hydroxymethyl)(2h-3,4,5,6-tetra Hydropyran-2-yloxy)]-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one

86. (2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-one

87. (s)-7-((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyl-tetrahydro-2h-pyran-2-yloxy)-tetrahydro-2h-pyran-2-yloxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one

88. 4h-1-benzopyran-4-one, 7-((2-o-(6-deoxy-alpha-l-mannapyranosyl)-beta-d-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl), (s)-

89. 4h-1-benzopyran-4-one, 7-((2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2s)-

90. 4h-1-benzopyran-4-one,7-[[2-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-,(s)-

91. 7-((2-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-one

92. 7-(2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyloxy)-2,3-dihydro-4,5,7-trihydroxyflavone;naringin

93. 7-[[2-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl]oxy]-5-hydroxy-2(s)-(4-hydroxyphenyl)-4h-1-benzopyran-4-one

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₃₂O₁₄
Molecular Weight	580.5 g/mol
XLogP3	-0.5
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	6
Exact Mass	580.17920569 g/mol
Monoisotopic Mass	580.17920569 g/mol
Topological Polar Surface Area	225 Å²
Heavy Atom Count	41
Formal Charge	0
Complexity	884
Isotope Atom Count	0
Defined Atom Stereocenter Count	11
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1