CHEMBL269671

Chemistry

Chemistry

Also known as: Qinghaosu, 63968-64-9, Huanghuahaosu, Artemisinine, Artemisine, (+)-artemisinin

Molecular Formula

C₁₅H₂₂O₅

Molecular Weight

282.33 g/mol

InChI Key

BLUAFEHZUWYNDE-NNWCWBAJSA-N

FDA UNII

9RMU91N5K2

(+)-artemisinin is a natural product found in Microliabum polymnioides, Artemisia tenuisecta, and other organisms with data available.

1 2D Structure

CHEMBL269671

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one

2.1.2 InChI

InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1

2.1.3 InChI Key

BLUAFEHZUWYNDE-NNWCWBAJSA-N

2.1.4 Canonical SMILES

CC1CCC2C(C(=O)OC3C24C1CCC(O3)(OO4)C)C

2.1.5 Isomeric SMILES

C[C@@H]1CC[C@H]2[C@H](C(=O)O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)C

2.2 Other Identifiers

2.2.1 UNII

9RMU91N5K2

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (3r,5as,6r,8as,9r,12s,12ar)-3,6,9-trimethyloctahydro-3,12-epoxypyrano(4,3-j)-1,2-benzodioxepin-10(3h)-one

2. Arteannuin

3. Artemisinine

4. Artemisininum

5. Huanghuahaosu

6. Qing Hao Su

7. Qinghaosu

8. Quing Hau Sau

9. Quinghaosu

2.3.2 Depositor-Supplied Synonyms

1. Qinghaosu

2. 63968-64-9

3. Huanghuahaosu

4. Artemisinine

5. Artemisine

6. (+)-artemisinin

7. Artemisinina

8. Artemisininum

9. Artemisinin [inn]

10. Qing Hau Sau

11. Nsc 369397

12. Chebi:223316

13. Octahydro-3,6,9-trimethyl-3,12-epoxy-12h-pyrano(4,3-j)-1,2-benzodioxepin-10(3h)-one

14. 9rmu91n5k2

15. Qinghosu

16. Quing Hau Sau

17. Astemisinin

18. (1r,4s,5r,8s,9r,12s,13r)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one

19. (3r,5as,6r,8as,9r,12s,12ar)-3,6,9-trimethyloctahydro-3,12-epoxypyrano[4,3-j][1,2]benzodioxepin-10(3h)-one

20. (3r,5as,6r,8as,9r,12s,12ar)-octahydro-3,6,9-trimethyl-3,12-epoxy-12h-pyrano(4,3-j)-1,2-benzodioxepin-10(3h)-one

21. Qing Hau Su

22. Qinghaosu [chinese]

23. Artemisinine [french]

24. Artemisininum [latin]

25. Artemisinina [spanish]

26. (+)-arteannuin

27. Qing Hau Sau [chinese]

28. Mfcd00081057

29. Artemisia Annua L., Extract

30. (1r,4s,5r,8s,9r,12s,13r)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-one

31. (3r,5as,6r,8as,9r,12s,12ar)-3,6,9-trimethyloctahydro-3,12-epoxypyrano(4,3-j)(1,2)benzodioxepin-10(3h)-one

32. (3r,5as,6r,8as,9r,12s,12ar)-octahydro-3,6,9-trimethyl-3,12-epoxy-12h-pyrano[4,3-j]-1,2-benzodioxepin-10(3h)-one

33. 1,5,9-trimethyl-(1r,4s,5r,9r,12s,13r)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one

34. Smr000578089

35. Sr-01000802560

36. Gnf-pf-5341

37. Artemsinin

38. Brn 4194670

39. Unii-9rmu91n5k2

40. Artemesinin

41. Artesin

42. Nsc-369397

43. Qinghaosu,artemisinine

44. Spectrum_001351

45. Artemisinin [mi]

46. Prestwick0_000498

47. Prestwick1_000498

48. Prestwick2_000498

49. Prestwick3_000498

50. Spectrum2_001512

51. Spectrum3_001549

52. Spectrum4_000721

53. Spectrum5_001098

54. Artemisinin [inci]

55. Ec 700-290-5

56. Artemisinin [mart.]

57. Schembl60304

58. Artemisinin [usp-rs]

59. Artemisinin [who-dd]

60. Artemisinin [who-ip]

61. Bspbio_000395

62. Bspbio_002998

63. Kbiogr_000982

64. Kbioss_001831

65. Mls001097650

66. Mls001304036

67. Mls002153846

68. Divk1c_000656

69. Spbio_001583

70. Spbio_002316

71. Bpbio1_000435

72. Chembl269671

73. Gtpl9954

74. Dtxsid2040652

75. Kbio1_000656

76. Kbio2_001831

77. Kbio2_004399

78. Kbio2_006967

79. Kbio3_002498

80. Ninds_000656

81. Hms2090i17

82. Hms2096d17

83. Hms2267n09

84. Hms3269l13

85. Hms3413p13

86. Hms3677p13

87. Hms3713d17

88. Pharmakon1600-01503042

89. 3,12-epoxy-12h-pyrano[4,3-j]-1,2-benzodioxepin-10(3h)-one, Octahydro-3,6,9-trimethyl-, (3r,5as,6r,8as,9r,12s,12ar)-

90. Bcp02096

91. Hy-b0094

92. Zinc8143788

93. Artemisininum [who-ip Latin]

94. Bdbm50088447

95. Nsc758216

96. Akos024457231

97. Ccg-220498

98. Cs-1794

99. Db13132

100. Lmpr0103190003

101. Nsc-758216

102. Idi1_000656

103. (3r,5as,6r,8as,9r,12s,12ar)-3,6,9-trimethyloctahydro-12h-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(3h)-one

104. 3,12-epoxy-12h-pyranol(4,3-j)-1,2-benzodioxepin-10(3h)-one, Octahydro-3,6,9-trimethyl-, (3-alpha,5a-beta,6-beta,8a-beta,9-alpha,12-beta,12ar*)-(+)-

105. As-12692

106. S1282

107. 968a649

108. Q426921

109. Sr-01000802560-2

110. Sr-01000802560-3

111. Sr-01000802560-4

112. Brd-k13112821-001-08-3

113. Brd-k13112821-001-17-4

114. 2ab44f63-5d0f-424a-aa3f-24062f9c1ced

115. (3r,5as,6r,8as,9r,12s,12ar)-3,6,9-trimethyloctahydro-3,12-epoxypyrano(4,3-j )-1,2-benzodioxepin-10(3h)-one

116. (3r,5as,6r,8as,9r,12s,12ar)-3,6,9-trimethyloctahydro-3h-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(12h)-one

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₂₂O₅
Molecular Weight	282.33 g/mol
XLogP3	2.8
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	0
Exact Mass	282.14672380 g/mol
Monoisotopic Mass	282.14672380 g/mol
Topological Polar Surface Area	54 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	452
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
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

Anti-Infective Agents

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

4.2 ATC Code

P - Antiparasitic products, insecticides and repellents

P01 - Antiprotozoals

P01B - Antimalarials

P01BE - Artemisinin and derivatives, plain

P01BE01 - Artemisinin