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Chemistry

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Also known as: (-)-eburnamonine, 4880-88-0, Vincamone, Eburnamonine, L-eburnamonine, Eburnal

Molecular Formula

C₁₉H₂₂N₂O

Molecular Weight

294.4 g/mol

InChI Key

WYJAPUKIYAZSEM-MOPGFXCFSA-N

FDA UNII

64UB2942IE

vinburnine is a natural product found in Kopsia pauciflora, Aspidosperma quebracho-blanco, and other organisms with data available.

1 2D Structure

Vinburnine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraen-17-one

2.1.2 InChI

InChI=1S/C19H22N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,18H,2,5,8-12H2,1H3/t18-,19+/m1/s1

2.1.3 InChI Key

WYJAPUKIYAZSEM-MOPGFXCFSA-N

2.1.4 Canonical SMILES

CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(=O)C2

2.1.5 Isomeric SMILES

CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4C(=O)C2

2.2 Other Identifiers

2.2.1 UNII

64UB2942IE

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (-)-eburnamonine

2. Cervoxan

3. Eburnamonine

4. Eburnamonine Monohydrochloride, (3alpha,16alpha)-isomer

5. Eburnamonine Phosphate, (3alpha,16alpha)-isomer

6. Eburnamonine, (3alpha,16alpha)-isomer

2.3.2 Depositor-Supplied Synonyms

1. (-)-eburnamonine

2. 4880-88-0

3. Vincamone

4. Eburnamonine

5. L-eburnamonine

6. Eburnal

7. Eburnamonine (-)

8. Vinburnine [inn]

9. Vincanorine

10. Dl-eburnamonine

11. Eburnamonine (-)-form

12. (+/-)-vincamone

13. (+/-)-eburnamonine

14. Vinburnine, (+/-)-

15. Ch-846

16. Eburnamonine (+/-)-form [mi]

17. 2580-88-3

18. Nsc-322920

19. Eburnamenin-14(15h)-one, (+/-)-

20. Chebi:4740

21. G54d0hmy25

22. 3.alpha.,16.alpha.-eburnamonine

23. 64ub2942ie

24. Vinburnine (inn)

25. Nsc322920

26. Eburnal Ritardo

27. Cis-vincamone

28. Dsstox_cid_25119

29. Dsstox_rid_80685

30. Dsstox_gsid_45119

31. (15s,19s)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraen-17-one

32. Vincamona [spanish]

33. Vinburnina

34. Vinburninum

35. Vincamona

36. Vinburninum [inn-latin]

37. Vinburnina [inn-spanish]

38. (-)-eburnamonina

39. (-)-eburnamonina [spanish]

40. (-)-vincamone

41. (3?,16?)-eburnamenin-14(15h)-one

42. 3-alpha,16-alpha-eburnamonine

43. Mls000758467

44. Einecs 225-490-5

45. Ch 846

46. Nsc 322920

47. 3alpha,16alpha-eburnamonine

48. Unii-g54d0hmy25

49. Eburnalritardo

50. Unii-64ub2942ie

51. (3alpha,16alpha)-eburnamenin-14(15h)-one

52. (3-alpha,16-alpha)-eburnamin-14(15h)-one

53. Eburnamin-14(15h)-one, (3-alpha,16-alpha)-

54. Ncgc00014750-02

55. Cervoxan (tn)

56. Prestwick_189

57. Cas-4880-88-0

58. Spectrum_000379

59. Prestwick0_000607

60. Prestwick1_000607

61. Prestwick2_000607

62. Prestwick3_000607

63. Spectrum2_001504

64. Spectrum3_001199

65. Spectrum4_000751

66. Spectrum5_000938

67. Vinburnine [mart.]

68. Ncistruc1_000941

69. Ncistruc2_000870

70. Vinburnine [who-dd]

71. Bspbio_000514

72. Bspbio_002877

73. Gtpl345

74. Kbiogr_001102

75. Kbioss_000859

76. Mls002153906

77. Divk1c_000411

78. Schembl456385

79. Spbio_001547

80. Spbio_002733

81. Bpbio1_000566

82. Megxp0_001871

83. Chembl1892145

84. Dtxsid6045119

85. Acon1_000004

86. Hms501e13

87. Kbio1_000411

88. Kbio2_000859

89. Kbio2_003427

90. Kbio2_005995

91. Kbio3_002377

92. Ninds_000411

93. Hms1569j16

94. Hms2096j16

95. Hms2233k13

96. Hms3713j16

97. Act03251

98. Bcp02373

99. Hy-b1180

100. Tox21_110060

101. Ccg-36740

102. Eburnamonine (-)-form [mi]

103. Nci322920

104. S5681

105. Zinc19796061

106. Akos015896486

107. Tox21_110060_1

108. Cs-4789

109. Db13793

110. Fd10193

111. Idi1_000411

112. Ncgc00262533-02

113. Ncgc00262533-03

114. Ac-26459

115. Bs-16859

116. Nci60_002800

117. Smr001233255

118. Sbi-0051740.p002

119. Eburnamenin-14(15h)-one, (3a,16a)-

120. C09149

121. D08676

122. A871877

123. Q2526386

124. Brd-k40227168-001-03-8

125. Brd-k40227168-001-06-1

126. (3alpha,16alpha)-eburnamenin-14(15h)-one, Vincamone]

127. Ncgc00262533-03_c19h22n2o_(3alpha,16alpha)-14,15-dihydroeburnamenin-14-one

128. (31s,6as)-6a-ethyl-31,4,5,6,6a,7-hexahydro-1h-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-8(2h)-one

129. (41s,13as)-13a-ethyl-2,3,5,6,13,13a-hexahydro-1h-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12(41h)-one

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₂N₂O
Molecular Weight	294.4 g/mol
XLogP3	3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	1
Exact Mass	294.173213330 g/mol
Monoisotopic Mass	294.173213330 g/mol
Topological Polar Surface Area	25.2 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	492
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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 MeSH Pharmacological Classification

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

4.2 ATC Code

C - Cardiovascular system

C04 - Peripheral vasodilators

C04A - Peripheral vasodilators

C04AX - Other peripheral vasodilators

C04AX17 - Vinburnine

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