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ACTIVE PHARMA INGREDIENTS

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Synopsis

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Chemistry

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Also known as: 42228-92-2, Antibiotic at 125, At-125, Acivicine, At 125, Acivicino

Molecular Formula

C₅H₇ClN₂O₃

Molecular Weight

178.57 g/mol

InChI Key

QAWIHIJWNYOLBE-OKKQSCSOSA-N

FDA UNII

O0X60K76I6

Acivicin is a modified amino acid and structural analog of glutamine. Acivicin inhibits glutamine amidotransferases in the purine and pyrimidine biosynthetic pathways, thereby inhibiting tumor growth in cell lines dependent on glutamine metabolism. (NCI04)

1 2D Structure

Acivicin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-amino-2-[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid

2.1.2 InChI

InChI=1S/C5H7ClN2O3/c6-3-1-2(11-8-3)4(7)5(9)10/h2,4H,1,7H2,(H,9,10)/t2-,4-/m0/s1

2.1.3 InChI Key

QAWIHIJWNYOLBE-OKKQSCSOSA-N

2.1.4 Canonical SMILES

C1C(ON=C1Cl)C(C(=O)O)N

2.1.5 Isomeric SMILES

C1[C@H](ON=C1Cl)[C@@H](C(=O)O)N

2.2 Other Identifiers

2.2.1 UNII

O0X60K76I6

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic Acid

2. Alpha-s,5s-alpha-amino-3-chloro-2-isoxazoline-5-acetic Acid

3. At 125

4. At-125

5. L-(alphas,5s)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic Acid

6. Nsc 163501

7. U 42,126

8. U-42,126

2.3.2 Depositor-Supplied Synonyms

1. 42228-92-2

2. Antibiotic At 125

3. At-125

4. Acivicine

5. At 125

6. Acivicino

7. Acivicinum

8. Nsc-163501

9. Acia

10. Nsc 163501

11. U 42126

12. U-42,126

13. Nsc163501

14. (2s)-2-amino-2-[(5s)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic Acid

15. U-42126

16. U 42,126

17. (alphas,5s)-alpha-amino-3-chloro-2-isoxazoline-5-acetic Acid

18. Chebi:74545

19. (s)-2-amino-2-((s)-3-chloro-4,5-dihydroisoxazol-5-yl)acetic Acid

20. O0x60k76i6

21. (alpha-s,5s)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic Acid

22. (2s)-amino[(5s)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]ethanoic Acid

23. Acivicin [usan:inn]

24. Acivicine [inn-french]

25. Acivicinum [inn-latin]

26. Acivicino [inn-spanish]

27. Unii-o0x60k76i6

28. Ncgc00095996-01

29. Brn 1074648

30. Spectrum_000343

31. Acivicin [usan]

32. Acivicin (usan/inn)

33. Acivicin [inn]

34. Spectrum3_001857

35. Spectrum4_000902

36. Spectrum5_001706

37. Acivicin [mart.]

38. Acivicin [who-dd]

39. Ncimech_000028

40. Schembl4159

41. Dsstox_cid_26010

42. Dsstox_rid_81286

43. Dsstox_gsid_46010

44. Bspbio_003274

45. Kbiogr_001364

46. Kbioss_000823

47. Divk1c_000672

48. Spectrum1502002

49. Acivicin, >=98% (hplc)

50. Chembl1231101

51. Dtxsid0046010

52. Gtpl11402

53. Hms502b14

54. Kbio1_000672

55. Kbio2_000823

56. Kbio2_003391

57. Kbio2_005959

58. Kbio3_002775

59. Ninds_000672

60. At125

61. Zinc3871381

62. Tox21_111545

63. (2s)-amino[(5s)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic Acid

64. (alphas,5s)-alpha-amino-3-chlor-4,5-dihydro-5-isoxazolylessigsaeure

65. (s-(r*,r*))-4,5-dihydro-alpha-amino-3-chloro-5-isoxazoleacetic Acid

66. Ccg-35436

67. Mfcd00866432

68. Akos027327575

69. Cs-w017302

70. Hy-w016586

71. Idi1_000672

72. Ncgc00178172-01

73. As-56028

74. Nci60_001241

75. Cas-42228-92-2

76. D02755

77. A825818

78. Q4674217

79. 5-isoxazoleacetic Acid,5-dihydro-, [s-(r*,r*)]-

80. Brd-k11632748-001-02-5

81. Alphas-amino-3-chloro-4,5s-dihydro-5-isoxazoleacetic Acid

82. (2s)-amino[(5s)-3-chloro-4,5-dihydroisoxazol-5-yl]ethanoic Acid

83. (s)-2-amino-2-((s)-3-chloro-4,5-dihydroisoxazol-5-yl)aceticacid

84. (.alpha.s,5s)-.alpha.-amino-3-chloro-2-isoxazoline-5-acetic Acid

85. (2s)-2-amino-2-[(5s)-3-chloro-4,5-dihydroisoxazol-5-yl]acetic Acid

86. (alphas,5s)-alpha-amino-3-chloro- 4,5-dihydro-5-isoxazol-acetic Acid

87. (alphas,5s)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazol-acetic Acid

88. (alphas,5s)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazole Acetic Acid

89. (alphas,5s)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic Acid

90. .alpha.-amino-3-chloro-4,5-dihydro-[s-(r*,r*)]-5-isoxazoleacetatic Acid

91. 5-isoxazoleacetic Acid, Alpha-amino-3-chloro-4,5-dihydro-, (s-(r*,r*))-

92. 5-isoxazoleacetic Acid, .alpha.-amino-3-chloro-4,5-dihydro-, (s-(r*,r*))-

93. 5-isoxazoleacetic Acid, 4,5-dihydro-alpha-amino-3-chloro-, (s-(r*,r*))-

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₅H₇ClN₂O₃
Molecular Weight	178.57 g/mol
XLogP3	-2.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	178.0145198 g/mol
Monoisotopic Mass	178.0145198 g/mol
Topological Polar Surface Area	84.9 Å²
Heavy Atom Count	11
Formal Charge	0
Complexity	206
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

Antimetabolites

Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Antimetabolites.)

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

Antimetabolites, Antineoplastic

Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)

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5-ISOXAZOLEACETIC ACID, .ALPHA.-AMINO-3-CHLORO-4,5-DIHYDRO-, (S-(R,R))-

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5-ISOXAZOLEACETIC ACID, .ALPHA.-AMINO-3-CHLORO-4,5-DIHYDRO-, (S-(R,R))-