API Import of Tox21_202427 obtained from Indian Customs Trade Statistics

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Chemistry

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Also known as: 91-64-5, 2h-chromen-2-one, 2h-1-benzopyran-2-one, 1,2-benzopyrone, Cumarin, Chromen-2-one
Molecular Formula
C9H6O2
Molecular Weight
146.14  g/mol
InChI Key
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
FDA UNII
A4VZ22K1WT

Coumarin
Coumarin is o hydroxycinnamic acid. Pleasant smelling compound found in many plants and released on wilting. Has anticoagulant activity by competing with Vitamin K.
1 2D Structure

Coumarin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
chromen-2-one
2.1.2 InChI
InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
2.1.3 InChI Key
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C2C(=C1)C=CC(=O)O2
2.2 Other Identifiers
2.2.1 UNII
A4VZ22K1WT
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,2-benzopyrone

2. 5,6-benzo-alpha-pyrone

2.3.2 Depositor-Supplied Synonyms

1. 91-64-5

2. 2h-chromen-2-one

3. 2h-1-benzopyran-2-one

4. 1,2-benzopyrone

5. Cumarin

6. Chromen-2-one

7. Rattex

8. Tonka Bean Camphor

9. Coumarinic Anhydride

10. Coumarine

11. Cis-o-coumarinic Acid Lactone

12. O-hydroxycinnamic Acid Lactone

13. Coumarinic Lactone

14. Benzo-alpha-pyrone

15. O-hydroxycinnamic Lactone

16. 2-oxo-1,2-benzopyran

17. Kumarin

18. 2h-benzo(b)pyran-2-one

19. Benzo-a-pyrone

20. Kumarin [czech]

21. 2h-1-benzopyran, 2-oxo-

22. 5,6-benzo-2-pyrone

23. 5,6-benzo-alpha-pyrone

24. 2h-benzo[b]pyran-2-one

25. Caswell No. 259c

26. O-coumaric Acid Lactone

27. O-hydroxyzimtsaure-lacton

28. Nci C07103

29. Cis-o-coumaric Acid Anhydride

30. Chromenone

31. Coumarinum

32. 103802-83-1

33. O-hydroxyzimtsaure-lacton [german]

34. Nsc 8774

35. 2-propenoic Acid, 3-(2-hydroxyphenyl)-, Delta-lactone

36. Epa Pesticide Chemical Code 127301

37. Brn 0383644

38. Benzo-.alpha.-pyrone

39. Cinnamic Acid, O-hydroxy-, Delta-lactone

40. Chebi:28794

41. Ai3-00753

42. Nsc-8774

43. O-hydroxycinnamic Acid Delta-lactone

44. 3-(2-hydroxyphenyl)-2-propenoic Delta-lactone

45. A4vz22k1wt

46. Chembl6466

47. Nci-c07103

48. 2-propenoic Acid, 3-(2-hydroxyphenyl)-delta-lactone

49. Mls000028741

50. Dtxsid7020348

51. Nsc8774

52. Ncgc00091502-01

53. Coumarin, >=98%

54. Smr000059040

55. 1-benzopyran-2-one

56. Dsstox_cid_348

57. 2h-chromene-2-one

58. Dsstox_rid_75529

59. Dsstox_gsid_20348

60. 2-propenoic Acid, 3-(2-hydroxyphenyl)-, D-lactone

61. 2-propenoic Acid, 3-(2-hydroxyphenyl)-, .delta.-lactone

62. Benzopyranone

63. Cas-91-64-5

64. Coumarin [nf]

65. Cou

66. Ccris 181

67. 2h-benzopyran-2-one

68. Hsdb 1623

69. Sr-01000721887

70. 2-oxo-2h-1-benzopyran

71. Einecs 202-086-7

72. Mfcd00006850

73. Unii-a4vz22k1wt

74. Chromen-one

75. A Coumarin

76. Coumarin-

77. D-lactone

78. Alpha-benzopyrone

79. Benzopyrylium Olate

80. Coumarin (dcf)

81. 1, 2-benzopyrone

82. A 1,2-benzopyrone

83. Venalot Mono (tn)

84. Coumarin (prohibited)

85. Spectrum_001336

86. St023509

87. Coumarin [hsdb]

88. Coumarin [iarc]

89. Coumarin [inci]

90. Opera_id_268

91. 2h-chromen-2-one #

92. 3-(2-hydroxyphenyl)-

93. Coumarin [mi]

94. 2h-1-benzopyran-2-on

95. Spectrum2_000303

96. Spectrum3_001772

97. Spectrum4_001818

98. Spectrum5_000555

99. Coumarinum [hpus]

100. Coumarin [mart.]

101. Bmse000077

102. Coumarin [who-dd]

103. Epitope Id:114082

104. Ec 202-086-7

105. Schembl6252

106. Wln: T66 Bovj

107. Bspbio_003263

108. Kbiogr_002460

109. Kbioss_001816

110. 5-17-10-00143 (beilstein Handbook Reference)

111. Mls001148422

112. Mls002454395

113. {2h-benzo[b]pyran-2-one}

114. Bidd:er0667

115. Spectrum1400208

116. Spbio_000266

117. Cinnamic Acid, .delta.-lactone

118. Coumarin, >=99% (hplc)

119. Bdbm12342

120. Kbio2_001816

121. Kbio2_004384

122. Kbio2_006952

123. Kbio3_002764

124. Zinc74709

125. Glxc-19130

126. Hms1923m11

127. Hms2091e19

128. Hms2232h18

129. Hms3369l08

130. Hms3652b05

131. Hms3885d09

132. Pharmakon1600-01400208

133. Amy37188

134. Hy-n0709

135. Tox21_111141

136. Tox21_202427

137. Tox21_300057

138. Ccg-38580

139. Nsc755852

140. S4170

141. Stk066167

142. Coumarin (prohibited) [fhfi]

143. Akos000120175

144. Tox21_111141_1

145. 2h-chromen-2-one (acd/name 4.0)

146. Cr-0048

147. Cs-8148

148. Db04665

149. Nsc-755852

150. Sdccgmls-0066912.p001

151. Ncgc00091502-02

152. Ncgc00091502-03

153. Ncgc00091502-04

154. Ncgc00091502-05

155. Ncgc00091502-06

156. Ncgc00091502-07

157. Ncgc00091502-08

158. Ncgc00091502-09

159. Ncgc00091502-11

160. Ncgc00091502-16

161. Ncgc00254092-01

162. Ncgc00259976-01

163. Coumarin 1000 Microg/ml In Acetonitrile

164. Nci60_041938

165. Sbi-0061760.p002

166. Db-057267

167. Cinnamic Acid, O-hydroxy-, .delta.-lactone

168. Coumarin, Vetec(tm) Reagent Grade, >=99%

169. Ft-0606287

170. Ft-0665197

171. N1707

172. Sw220278-1

173. A14543

174. Bim-0061760.0001

175. C05851

176. D07751

177. D81844

178. Ab00375898_11

179. Ab00375898_12

180. Coumarin, Primary Pharmaceutical Reference Standard

181. Q111812

182. Cu-01000013121-2

183. Q-100890

184. Sr-01000721887-2

185. Sr-01000721887-3

186. Brd-k23913458-001-02-5

187. Brd-k23913458-001-13-2

188. Coumarin, Certified Reference Material, Tracecert(r)

189. Z57169486

190. Coumarin, European Pharmacopoeia (ep) Reference Standard

191. F3096-1712

192. Coumarin (constituent Of Cinnamomum Cassia Bark) [dsc]

193. Coumarin (constituent Of Cinnamomum Verum Bark) [dsc]

194. D3e956c4-9541-4f57-9435-7d915c38e19e

195. 2h-1-benzopyran-2-one;coumarin;2h-chromen-2-one;coumarin ;coumarin (2h-1-benzopyran-2-one) (chromen-2-one);2h-1-benzopyran-2-one Coumarin 2h-chromen-2-one Coumarin Coumarin (2h-1-benzopyran-2-one) (chromen-2-one)

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 146.14 g/mol
Molecular Formula C9H6O2
XLogP31.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass146.036779430 g/mol
Monoisotopic Mass146.036779430 g/mol
Topological Polar Surface Area26.3 Ų
Heavy Atom Count11
Formal Charge0
Complexity196
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

A species difference has been reported for the excretion of an oral dose of (14)C-coumarin. Within 4 days rats excreted 47% of the label in the urine and 39% in the feces, whereas rabbits excreted 92% in the urine and negligible amount in the feces.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 87


Female rabbits dosed orally with 50 mg/kg of 3-14C-coumarin excreted over 80% of the label in the urine in 24 hours. No label was found in the expired air and only a small amount in the feces.

Joint Expert Committee on Food Additives; WHO Food Additive Series #16, Coumarin. Available from, as of March 21, 2003: https://www.inchem.org/documents/jecfa/jecmono/v16je10.htm


The reason for the considerable fecal excretion of (14)C /after oral administration of (14)C-coumarin/ in rat... may represent unabsorbed material.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 87


Twenty-four hr after an IP dose to rats of... (14)C-coumarin, 38% had been excreted in the urine, 13% in the feces, 30% was excreted in the air as (14)C-carbon dioxide and 9% of the remainder was mainly present in the cecum.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 151


For more Absorption, Distribution and Excretion (Complete) data for COUMARIN (14 total), please visit the HSDB record page.


4.2 Metabolism/Metabolites

...Recombinant human and rat CYP1A forms and recombinant human CYP2E1 readily catalyzed CE /coumarin-3,4-epoxide/ production. Coinhibition with CYP1A1/2 and CYP2E1 antibodies blocked CE formation by 38, 84, and 67 to 92% (n=3 individual samples) in mouse, rat, and human hepatic microsomes, respectively. Although CYP1A and 2E forms seem to be the most active catalysts of CE formation in liver, studies conducted with the mechanism-based inhibitor 5-phenyl-pentyne demonstrated that CYP2F2 is responsible for up to 67% of CE formation in whole mouse lung microsomes. In contrast to the CE pathway, coumarin 3-hydroxylation is a minor product of coumarin in liver microsomes from mice, rats, and humans and is catalyzed predominately by CYP3A and CYP1A forms, confirming that CE and 3-hydroxycoumarin are formed via distinct metabolic pathways.

PMID:11950775 Born SL et al; Drug Metab Dispos 30 (5): 483-7 (2002)


...To examine species differences in CYP2A function, liver microsomes from nine mammalian species (rat, mouse, hamster, rabbit, guinea pig, cat, dog, cynomolgus monkey and human were tested for their ability to catalyze the 7 alpha- and 15 alpha-hydroxylation of testosterone and the 7-hydroxylation of coumarin. Antibody against rat CYP2Al recognized one or more proteins in liver microsomes from all mammalian species examined. However, liver microsomes from cat, dog, cynomolgus monkey, and human catalyzed negligible rates of testosterone 7 alpha- and/or 15 alpha-hydroxylation, whereas rat and cat liver microsomes catalyzed negligible rates of coumarin 7-hydroxylation. Formation of 7-hydroxycoumarin accounted for a different proportion of the coumarin metabolites formed by liver microsomes from each of the various species examined. 7-Hydroxycoumarin was the major metabolite (>70%) in human and monkey, but only a minor metabolite (<1%) in rat. The 7-hydroxylation of coumarin by human liver microsomes was catalyzed by a single, high-affinity enzyme (Km 0.2-0.6 uM, which was markedly inhibited (>95%) by antibody against rat CYP2Al. The rate of coumarin 7-hydroxylation varied approximately 17-fold among liver microsomes from 22 human subjects. This variation was highly correlated (r2=0.956) with interindividual differences in the levels of CYP2A6... . These results indicate that CYP2A6 is largely or entirely responsible for catalyzing the 7-hydroxylation of coumarin in human liver, microsomes. Treatment of monkeys with phenobarbital or dexamethasone increased coumarin 7-hydroxylase activity, whereas treatment with beta-naphthoflavone caused a slight decr. In contrast to rats and mice, the expression of CYP2A enzymes in cynomolgus monkeys and humans was not sexually differentiated. Despite their structural similarity to coumarin, the anticoagulants dicumarol and warfarin do not appear to be substrates for CYP2A6. ...

PMID:1381906 Pearce R et al; Arch Biochem Biophys 298 (1): 211-25 (1992)


/The rat can/ hydroxylate coumarin in the 3-position. As can... the rabbit... .

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 191


The hepatic enzyme system, coumarin-7-hydroxylase, responsible for a high proportion of the hydroxylation of coumarin in cats, guinea pigs, hamsters, rabbits, and especially in man, is absent from the livers of ferrets, mice and rats. Rat liver contains an inhibitor of this enzyme.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 399


For more Metabolism/Metabolites (Complete) data for COUMARIN (15 total), please visit the HSDB record page.


Coumarin has known human metabolites that include 3-Hydroxycoumarin, 7-Hydroxycoumarin, and Coumarin 3,4-epoxide.

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


4.3 Mechanism of Action

Coumarin and some of its metabolites have been shown to inhibit glucose-6-phosphatase in liver and in liver microsomal preparation. It interferes with excision repair processes on ultra-violet-damaged DNA and with host cell reactivation of ultra-violet-irradiated phage T1 in E coli WP2.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V10 116


Both 4-hydroxycoumarin derivatives and indandiones (also known as oral anticoagulants) are antagonists of vitamin K. Their use as rodenticides is based on the inhibition of the vitamin K-dependent step in the synthesis of a number of blood coagulation factors. The vitamin K-dependent proteins ...in the coagulation cascade... are the procoagulant factors II (prothrombin), VII (proconvertin), IX (Christmas factor) and X (Stuart-Prower factor), and the coagulation-inhibiting proteins C and S. All these proteins are synthesized in the liver. Before they are released into the circulation the various precursor proteins undergo substantial (intracellular) post-translational modification. Vitamin K functions as a co-enzyme in one of these modifications, namely the carboxylation at well-defined positions of 10-12 glutamate residues into gamma-carboxyglutamate (Gla). The presence of these Gla residues is essential for the procoagulant activity of the various coagulations factors. Vitamin K hydroquinone (KH2) is the active co-enzyme, and its oxidation to vitamin K 2,3-epoxide (KO) provides the energy required for the carboxylation reaction. The epoxide is than recycled in two reduction steps mediated by the enzyme KO reductase... . The latter enzyme is the target enzyme for coumarin anticoagulants. Their blocking of the KO reductase leads to a rapid exhaustion of the supply of KH2, and thus to an effective prevention of the formation of Gla residues. This leads to an accumulation of non-carboxylated coagulation factor precursors in the liver. In some cases these precursors are processed further without being carboxylated, and (depending on the species) may appear in the circulation. At that stage the under-carboxylated proteins are designated as descarboxy coagulation factors. Normal coagulation factors circulate in the form of zymogens, which can only participate in the coagulation cascade after being activated by limited proteolytic degradation. Descarboxy coagulation factors have no procoagulant activity (i.e. they cannot be activated) and neither they can be converted into the active zymogens by vitamin K action. Whereas in anticoagulated humans high levels of circulating descarboxy coagulation factors are detectable, these levels are negligible in warfarin-treated rats and mice. /Anticoagulant rodenticides/

WHO; Environ Health Criteria 175: Anticoagulant Rodenticides p.46 (1995)


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07-Jan-2021
31-Aug-2024
KGS
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