Prestwick3_000474

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Also known as: 94-62-2, 1-piperoylpiperidine, Bioperine, Piperin, 7780-20-3, Fema no. 2909

Molecular Formula

C₁₇H₁₉NO₃

Molecular Weight

285.34 g/mol

InChI Key

MXXWOMGUGJBKIW-YPCIICBESA-N

FDA UNII

U71XL721QK

piperine is a natural product found in Macropiper, Piper boehmeriifolium, and other organisms with data available.

1 2D Structure

Prestwick3_000474

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one

2.1.2 InChI

InChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+

2.1.3 InChI Key

MXXWOMGUGJBKIW-YPCIICBESA-N

2.1.4 Canonical SMILES

C1CCN(CC1)C(=O)C=CC=CC2=CC3=C(C=C2)OCO3

2.1.5 Isomeric SMILES

C1CCN(CC1)C(=O)/C=C/C=C/C2=CC3=C(C=C2)OCO3

2.2 Other Identifiers

2.2.1 UNII

U71XL721QK

2.3 Synonyms

2.3.1 MeSH Synonyms

1. ((1-5-(1,3)-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine

2. (1-(5-(1,3)-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine

3. 1-piperoylpiperidine

4. Piperine, (e,e)-isomer

5. Piperine, (e,z)-isomer

6. Piperine, (z,e)-isomer

7. Piperine, (z,z)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 94-62-2

2. 1-piperoylpiperidine

3. Bioperine

4. Piperin

5. 7780-20-3

6. Fema No. 2909

7. (e,e)-1-piperoylpiperidine

8. N-[(e,e)-piperoyl]piperidine

9. (2e,4e)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

10. Ai 3-01439

11. Piperidine, 1-piperoyl-, (e,e)-

12. Piperidine, 1-[(2e,4e)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-

13. (2e,4e)-5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

14. Nsc-21727

15. 1-[(2e,4e)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl]piperidine

16. (2e,4e)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one

17. N-(e,e)-piperoyl-piperidine

18. Chembl43185

19. U71xl721qk

20. Chebi:28821

21. Nsc21727

22. Piperoylpiperidine

23. Piperidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-, (e,e)-

24. Piperidine, 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-, (e,e)-

25. Dsstox_cid_1805

26. Piperidine, 1-(5-(3,4-methylenedioxyphenyl)-1-oxo-2,4-pentadienyl)-

27. 1-[(2e,4e)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine

28. Dsstox_rid_76339

29. Dsstox_gsid_21805

30. 1-[(2e,4e)-5-(1,3-benzodioxol-5-yl)-2,4-pentadienoyl]piperidine

31. 5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

32. Piperidine, 1-((2e,4e)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-

33. Piperine [usp]

34. Smr000112278

35. Ccris 5572

36. Piperine (aliphatic)

37. 1-piperoylpiperidine, (e,e)-

38. Sr-01000638580

39. Piperidine, 1-piperoyl-

40. Einecs 202-348-0

41. Nsc 21727

42. Unii-u71xl721qk

43. (2e,4e)-5-(1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

44. (2e,4e)-5-(benzo(d)(1,3)dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

45. Cas-94-62-2

46. Piperine,(s)

47. 1-piperylpiperidine

48. Prestwick_398

49. Black Pepper Extract

50. Mfcd00005839

51. 1,3-benzodioxol-5-yl-1-oxo-2,4-pentadienyl-piperine

52. 1-piperoyl-piperidine

53. Nsc 242267

54. Piperine, >=97%

55. St079380

56. Starbld0008505

57. Piperidine, (e,e)-

58. Piperine [fhfi]

59. Piperine [inci]

60. Ai3-01439

61. Piperine [mi]

62. Prestwick2_000474

63. Prestwick3_000474

64. Spectrum5_001507

65. Piperine [usp-rs]

66. Piperine [who-dd]

67. 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine, (e,e)-

68. Piperine, >=97%, Fg

69. Schembl94058

70. Schembl94059

71. Bspbio_000608

72. Bspbio_002515

73. Piperine, Analytical Standard

74. Mls002153830

75. Mls002473213

76. Bidd:er0675

77. Spectrum1500873

78. Bpbio1_000670

79. Gtpl2489

80. N-ee-piperoyl-piperidine

81. Dtxsid3021805

82. Piperine (1-piperoylpiperidine)

83. Chebi:93043

84. Fema 2909

85. Hms502p16

86. 2,4-pentadien-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-, (2e,4e)-

87. Hms1569o10

88. Hms1921m12

89. Hms2092m22

90. Hms2096o10

91. Hms2270m18

92. Pharmakon1600-01500873

93. 1-trans,trans-piperinoyl-piperidine

94. Amy40672

95. Bcp18901

96. Hy-n0144

97. Zinc1529772

98. Tox21_201990

99. Tox21_302746

100. 1-(5-(3,4-methylenedioxyphenyl)-1-oxo-2,4-pentadienyl)piperidine

101. 1-piperoyl-(e,e)-piperidine

102. Bbl027541

103. Bdbm50148573

104. Ccg-39991

105. Nsc757803

106. S2344

107. Stl377909

108. (2e,4e)-5-(1,3-benzodioxol-5-yl)-1-(1-piperidyl)penta-2,4-dien-1-one

109. Akos003369047

110. Cs-6155

111. Db12582

112. Nsc-757803

113. Sdccgmls-0066693.p001

114. Idi1_000954

115. (piperidin-1-yl)penta-2,4-dien-1-one

116. Ncgc00094872-01

117. Ncgc00094872-02

118. Ncgc00094872-03

119. Ncgc00094872-04

120. Ncgc00094872-05

121. Ncgc00094872-06

122. Ncgc00094872-09

123. Ncgc00256392-01

124. Ncgc00259539-01

125. Ac-11746

126. As-17442

127. Ls-14576

128. Sbi-0051621.p002

129. Cs-0368434

130. N1674

131. P0460

132. Sw196642-2

133. C03882

134. P-6920

135. Ab00052185_08

136. Ag-205/01792022

137. Q414501

138. (2e,4e)-5-(benzo[d][1,3]dioxol-5-yl)-1-

139. Sr-01000638580-1

140. Sr-01000638580-2

141. Sr-01000638580-5

142. Sr-01000638580-6

143. Brd-k59522102-001-08-8

144. Piperine (constituent Of Black Pepper) [dsc]

145. Q27164772

146. 1,3-benzodioxol-5-yl-1-oxo-2,4-pentadienyl-piperidine

147. Piperine, European Pharmacopoeia (ep) Reference Standard

148. 1-[5-(1,3-benzodioxol-5-yl)-2,4-pentadienoyl]piperidine

149. 4-(1,3-benzodioxole-5-yl)-1,3-butenylpiperidino Ketone

150. Piperine, United States Pharmacopeia (usp) Reference Standard

151. 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-1-penta-2,4-dienone

152. Piperidine,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-, (e,e)-

153. (e,e) 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine

154. (e,e)-1-(5-(1,3-benzodioxol-5-yl)-2,4-pentadienoyl)piperidine

155. 1-[(2e,4e)-5-(1,3-benzodioxol-5-yl)-2,4-pentadienoyl]piperidine #

156. 147030-08-8

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₉NO₃
Molecular Weight	285.34 g/mol
XLogP3	3.5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	285.13649347 g/mol
Monoisotopic Mass	285.13649347 g/mol
Topological Polar Surface Area	38.8 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	412
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Cytochrome P-450 Enzyme Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 ENZYMES. (See all compounds classified as Cytochrome P-450 Enzyme Inhibitors.)