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    Artemisinin

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    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

    2D Structure

    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 Weight 282.33 g/mol
    Molecular Formula C15H22O5
    XLogP32.8
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count0
    Exact Mass282.14672380 g/mol
    Monoisotopic Mass282.14672380 g/mol
    Topological Polar Surface Area54 Ų
    Heavy Atom Count20
    Formal Charge0
    Complexity452
    Isotope Atom Count0
    Defined Atom Stereocenter Count7
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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