1416-01-9

Synopsis, Chemistry

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Also known as: 153-18-4, Rutoside, Quercetin 3-rutinoside, Birutan, Phytomelin, Myrticolorin

Molecular Formula

C₂₇H₃₀O₁₆

Molecular Weight

610.5 g/mol

InChI Key

IKGXIBQEEMLURG-NVPNHPEKSA-N

FDA UNII

5G06TVY3R7

A flavonol glycoside found in many plants, including BUCKWHEAT; TOBACCO; FORSYTHIA; HYDRANGEA; VIOLA, etc. It has been used therapeutically to decrease capillary fragility.

1 2D Structure

1416-01-9

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one

2.1.2 InChI

InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1

2.1.3 InChI Key

IKGXIBQEEMLURG-NVPNHPEKSA-N

2.1.4 Canonical SMILES

CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O

2.1.5 Isomeric SMILES

C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

5G06TVY3R7

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-rhamnosyl-glucosyl Quercetin

2. Quercetin 3 Rutinoside

3. Quercetin, 3-rhamnosyl-glucosyl

4. Quercetin-3-rutinoside

5. Rutoside

2.3.2 Depositor-Supplied Synonyms

1. 153-18-4

2. Rutoside

3. Quercetin 3-rutinoside

4. Birutan

5. Phytomelin

6. Myrticolorin

7. Eldrin

8. Globulariacitrin

9. Rutin Trihydrate

10. Ilixanthin

11. Osyritrin

12. Paliuroside

13. Tanrutin

14. Sophorin

15. Bioflavonoid

16. Globularicitrin

17. Rutabion

18. Venoruton

19. 3-rutinosyl Quercetin

20. Violaquercitrin

21. Yunxianggan

22. 3-rhamnoglucosylquercetin

23. Rutine

24. Rutozyd

25. Melin

26. Quercetin 3-o-rutinoside

27. Rutinic Acid

28. Birutan Forte

29. Quercetin-3-rutinoside

30. Oxyritin

31. Rutinum

32. Rutosido

33. Rutosidum

34. Rutinion Acid

35. Vitamin P

36. Quercitin 3-rutinoside

37. Novarrutina

38. Violaquercetrin

39. Birutin

40. Quercetin Rhamnoglucosine

41. Quercetin-3-o-rutinoside

42. Quercetin-3beta-rutinoside

43. Quercetin 3-rhamnoglucoside

44. Quercetol 3-rhamnoglucoside

45. C.i. 75730

46. Rutosid

47. Rutoside [inn]

48. 3,3',4',5,7-pentahydroxyflavone-3-rutinoside

49. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-((((2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)methyl)tetrahydro-2h-pyran-2-yl)oxy)-4h-chromen-4-one

50. Quercetin 3-o-beta-d-rutinoside

51. 5g06tvy3r7

52. Chembl226335

53. Chebi:28527

54. Rutoside (inn)

55. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4h-chromen-3-yl 6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranoside

56. 3-[[6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4h-1-benzopyran-4-one

57. 3-rhamnoglucoside Of 3,3',4',5,7-pentahydroxyflavone

58. Ncgc00160628-01

59. Nsc-9220

60. Dsstox_cid_2326

61. Dsstox_rid_76549

62. Dsstox_gsid_22326

63. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one

64. 4h-1-benzopyran-4-one,3-[[6-o-(6-deoxy-a-l-mannopyranosyl)-b-d-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-

65. Rut

66. Rutoside (rutin)

67. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one

68. 3-((6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4h-1-benzopyran-4-one

69. Cas-153-18-4

70. Smr000112560

71. Rutin [jan:nf]

72. Rutosidum [inn-latin]

73. Rutosido [inn-spanish]

74. Usaf Cf-5

75. Unii-5g06tvy3r7

76. Neoisorutin

77. Ccris 7564

78. Rutinoside, Quercetin-3, Beta-

79. Hydroxyethylrutoside

80. Rutin (rutoside)

81. Venoruton (tn)

82. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4h-chromen-3-yl 6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-mannopyranoside

83. Nsc 9220

84. Einecs 205-814-1

85. Mfcd00006830

86. Rutin,(s)

87. Brn 0075455

88. 3,3',4',5,7-pentahydroxyflavone 3-rutinoside

89. Ai3-19098

90. Rutin [vandf]

91. Rutin [inci]

92. 207671-50-9

93. Rutin [dsc]

94. Rutin [usp-rs]

95. Rutin [mi]

96. Rutoside [inn:jan:nf]

97. Rutoside [who-dd]

98. Beta-quercetin-3-rutinoside

99. Bidd:pxr0020

100. Schembl23243

101. 4h-1-benzopyran-4-one, 3-((6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-

102. 5-18-05-00519 (beilstein Handbook Reference)

103. Mls000759398

104. Mls001424098

105. Bidd:er0377

106. Divk1c_000644

107. Megxp0_000068

108. Rutin From Sophora Japonica L.

109. Dtxsid3022326

110. Acon1_000075

111. Cid_5280805

112. Hms502a06

113. Kbio1_000644

114. Rutin (95%)

115. Ninds_000644

116. 3,3',4',5,7-pentahydroxyflavone-3-rhamnoglucoside

117. Hms2051b06

118. 3'4'5,7-tetoh-flavone-3-rut

119. Flavone, 3,3',4',5,7-pentahydroxy-, 3-(o-rhamnosylglucoside)

120. Hy-n0148

121. Zinc4096846

122. Quercetin 3-o-beta-delta-rutinoside

123. Tox21_111945

124. Tox21_202602

125. Bdbm50217942

126. Glucopyranoside, Quercetin-3 6-o-alpha-l-rhamnopyranosyl-, Beta-d

127. Quercetin, 3-(6-o-alpha-l-rhamnopyranosyl-beta-d-glucopyranoside)

128. S2350

129. 3,3',4',5,5',7-hexahydroxyflavone (6-o-alpha-l-rhamnosyl-beta-d-glucoside)

130. Akos015895432

131. Glucopyranoside, Quercetin-3 6-o-(6-deoxy-alpha-l-mannopyranosyl)-, Beta-d-

132. Quercetin, 3-(6-0-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranoside)

133. Tox21_111945_1

134. Ccg-100999

135. Cs-5573

136. Db01698

137. Ds-9708

138. Nc00249

139. Idi1_000644

140. Rutinoside, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4h-1-benzopyran-3-yl

141. Ncgc00160628-02

142. Ncgc00160628-03

143. Ncgc00260150-01

144. 4h-1-benzopyran-4-one, 3-[[6-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-

145. Methyltetrahydro-2h-pyran-2-yloxy)methyl)

146. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3

147. R0035

148. C05625

149. D08499

150. Ab00374708-09

151. Tetrahydro-2h-pyran-2-yloxy)-4h-chromen-4-one

152. A809400

153. Q407857

154. Sr-01000759399

155. Q-201691

156. Sr-01000759399-5

157. A8241da0-6ec6-48ba-bd10-3f7bd61d42ce

158. Brd-k20482099-001-01-1

159. Brd-k20482099-001-11-0

160. 3,3,4,5,7-pentahydroxyflavone-3-rhamnoglucoside

161. 3-rhamnoglucoside Of 5,7,3',4'-tetrahydroxyflavonol

162. Quercetin 3-o-[alpha-l-rhamnosyl-(1->6)-beta-d-glucoside]

163. Quercetin 3-o-.alpha.-l-rhamnopyranosyl-.beta.-d-glucopyranoside

164. Rutin (quercetin-3-o-rutinoside) (constituent Of Ginkgo) [dsc]

165. Rutin (quercetin-3-o-rutinoside) (constituent Of Hawthorn Leaf With Flower) [dsc]

166. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-((((2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)methyl)tetrahydro-2h-pyran-2-yl)oxy)-4h-chromen-4-one;rutin

167. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(((2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)methyl)tetrahydro-2h-pyran-2-yloxy)-4h-chromen-4-one

168. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4h-chromen-4-one

169. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4h-chromen-4-one-3-yl 6-o-.alpha.-l-rhamnopyranosyl-.beta.-d-glucoside

170. 4h-1-benzopyran-4-one, 3-[[6-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl]-oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₃₀O₁₆
Molecular Weight	610.5 g/mol
XLogP3	-1.3
Hydrogen Bond Donor Count	10
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	6
Exact Mass	610.15338487 g/mol
Monoisotopic Mass	610.15338487 g/mol
Topological Polar Surface Area	266 Å²
Heavy Atom Count	43
Formal Charge	0
Complexity	1020
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
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 ATC Code

C05CA01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

C - Cardiovascular system

C05 - Vasoprotectives

C05C - Capillary stabilizing agents

C05CA - Bioflavonoids

C05CA01 - Rutoside