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Chemistry

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Also known as: 522-12-3, Quercetin 3-rhamnoside, Quercitroside, Quercetin 3-o-rhamnoside, Quercetrin, Quercimelin
Molecular Formula
C21H20O11
Molecular Weight
448.4  g/mol
InChI Key
OXGUCUVFOIWWQJ-HQBVPOQASA-N
FDA UNII
2Y8906LC5P

Quercitrin
quercitrin is a natural product found in Xylopia emarginata, Lotus ucrainicus, and other organisms with data available.
1 2D Structure

Quercitrin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
2.1.2 InChI
InChI=1S/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21-/m0/s1
2.1.3 InChI Key
OXGUCUVFOIWWQJ-HQBVPOQASA-N
2.1.4 Canonical SMILES
CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
2.1.5 Isomeric SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
2.2 Other Identifiers
2.2.1 UNII
2Y8906LC5P
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Quercetin 3-o-alpha-l-rhamnopyranoside

2. Quercetin 3-o-alpha-l-rhamnoside

3. Quercetin 3-o-alpha-rhamnopyranoside

4. Quercetin 3-o-l-rhamnoside

5. Quercetin 3-o-rhamnopyranoside

6. Quercetin 3-o-rhamnoside

7. Quercetin 3-rhamnopyranoside

8. Quercetin 3-rhamnoside

9. Quercetin-3-l-rhamnoside

10. Quercetin-3-o-alpha-rhamnoside

11. Quercetrin

12. Quercimelin

13. Quercitroside

14. Thujin

2.3.2 Depositor-Supplied Synonyms

1. 522-12-3

2. Quercetin 3-rhamnoside

3. Quercitroside

4. Quercetin 3-o-rhamnoside

5. Quercetrin

6. Quercimelin

7. Thujin

8. Quercetin 3-l-rhamnoside

9. Quercetin-3-l-rhamnoside

10. Quercitronic Acid

11. Quercetin-3-rhamnoside

12. Quercetin 3-o-alpha-l-rhamnoside

13. Quercetin 3-o-l-rhamnoside

14. Quercetin 3-o-rhamnopyranoside

15. Chebi:17558

16. C.i. 75720

17. Quercetin 3-o-alpha-rhamnopyranoside

18. 3,3',4',5,7-pentahydroxyflavone-3-l-rhamnoside

19. Nsc9221

20. Quercetin, 3-(6-deoxy-alpha-l-mannopyranoside)

21. 2y8906lc5p

22. Mannopyranoside, Quercetin-3 6-deoxy-, Alpha-l-

23. Usaf Cf-2

24. Mfcd00016932

25. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-4h-chromen-4-one

26. Rhamnosyl-3-quercitin

27. Quercitin-3-rhamnoside

28. Luteolin 6-deoxy-alpha-l-mannopyranoside

29. Rhamnoside, Quercetin-3

30. Quercetin-3-o-rhamnoside

31. Quercetin 3-o-alpha-l-rhamnopyranoside

32. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4h-chromen-3-yl 6-deoxy-alpha-l-mannopyranoside

33. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one

34. 4h-1-benzopyran-4-one, 3-((6-deoxy-.alpha.-l-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-

35. Quercetrin-3-o-rham

36. Chembl82242

37. Nsc-9221

38. Unii-2y8906lc5p

39. Quercetin 3-o-.alpha.-l-rhamnoside

40. Hsdb 4339

41. 4gue

42. Nci-c60102

43. Quercitroside,(s)

44. 4h-1-benzopyran-4-one, 3-[(6-deoxy-.alpha.-l-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-

45. Qct

46. Quercetin 3-rhamnopyranoside

47. Einecs 208-322-5

48. 3-rhamnosyl Quercetin

49. Brn 0068135

50. 5,7-dihydroxy-3-

51. Ci 75720

52. Quercitrin [mi]

53. Ai3-36095

54. Quercitrin [hsdb]

55. Bidd:pxr0076

56. 2-(3,4-dihydroxyphenyl)-

57. 5-18-05-00514 (beilstein Handbook Reference)

58. Mls002472998

59. 3-o-rhamnosylquercetin

60. Schembl147092

61. Flavone, 3,3',4',5,7-pentahydroxy-, 3-rhamnoside

62. Megxp0_000185

63. Acon1_000189

64. Bdbm84978

65. Cid_5280459

66. 5-trihydroxy-6-methyltetrahydro-

67. Dtxsid50200230

68. Hms2219d24

69. Hy-n0418

70. Zinc4175638

71. Bdbm50056315

72. S3824

73. Akos000278033

74. Flavone, 3,3',4',5,7-pentahydroxy-, 3-(6-deoxy-alpha-l-mannopyranoside)

75. Ccg-269215

76. Cs-5408

77. Smp1_000253

78. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one

79. 3-((6-deoxy-alpha-l-mannopyranosyl)-oxy)-2-(3,4-dihydr Oxyphenyl)-5,7-dihydroxy-4h-1-benzopyran-4-one

80. 4h-1-benzopyran-4-one, 3-((6-deoxy-alpha-l-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-

81. Ac-20295

82. Ac-34266

83. Bs-16996

84. Quercetin-3-o-.alpha.-rhamnoside

85. Smr001397103

86. Wa 17779

87. N1840

88. 3-o-.alpha.-l-rhamnopyranosylquercetin

89. C01750

90. Quercetin 3-o-.alpha.-rhamnopyranoside

91. Quercetin 3-o-.alpha.-l-rhamnopyranoside

92. ((2s,3r,4r,5r,6s)-3,4,

93. 522q123

94. Q-100588

95. Q-100945

96. Q1649777

97. Quercitrin, Primary Pharmaceutical Reference Standard

98. Brd-k98601533-001-01-7

99. Flavone, 3,3',4',5, 7-pentahydroxy-, 3-rhamnoside

100. 5,7,3',4'-tetrahydroxyflavonol 3-o-rhamnoside

101. 3,3',4',5,7-pentahydroxyflavone 3-l-rhamnoside

102. 3-o-a-l-rhamnopyranosyloxy-3',4',5,7-tetrahydroxyflavone

103. Quercitrin (quercetin-3-o- Rhamnoside) (constituent Of Ginkgo) [dsc]

104. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)-4h-chromen-4-one

105. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4h-chromen-4-one

106. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4h-chromen-3-yl 6-deoxy-.alpha.-l-mannopyranoside

107. 3-((6-deoxy-.alpha.-l-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4h-1-benzopyran-4-one

108. 3-((6-deoxy-alpha-l-mannopyranosyl)-oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4h-1-benzopyran-4-one

109. 3-((6-deoxy-alpha-l-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4h-benzopyran-4-one

110. 3-[(6-deoxy-a-l-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4h-benzopyran-4-one

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 448.4 g/mol
Molecular Formula C21H20O11
XLogP30.9
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count11
Rotatable Bond Count3
Exact Mass448.10056145 g/mol
Monoisotopic Mass448.10056145 g/mol
Topological Polar Surface Area186 Ų
Heavy Atom Count32
Formal Charge0
Complexity741
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Metabolism/Metabolites

YIELDS QUERCETIN IN ASPERGILLUS; WESTLAKE DWS, CAN J MICROBIOL 9: 211 (1963); YIELDS QUERCITRIN QUINONE PROBABLY IN POLYPORUS; PICKARD MA & WESTLAKE DWS, CAN J BIOCHEM 48: 1351 (1970). /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. Q-2


Quercitrin has known human metabolites that include L-Rhamnose, Quercetin, and alpha-L-Rhamnose.

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


REF. STANDARDS & IMPURITIES

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