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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: 1-methyl-d-tryptophan, 110117-83-4, D-1mt, D-tryptophan, 1-methyl-, D-1-methyltryptophan, Indoximod (nlg-8189)

Molecular Formula

C₁₂H₁₄N₂O₂

Molecular Weight

218.25 g/mol

InChI Key

ZADWXFSZEAPBJS-SNVBAGLBSA-N

FDA UNII

TX5CYN1KMZ

Indoximod is a methylated tryptophan with immune checkpoint inhibitory activity. Indoximod inhibits the enzyme indoleamine 2,3-dioxygenase (IDO), which degrades the essential amino acid tryptophan, and may increase or maintain tryptophan levels important to T cell function. Tryptophan depletion is associated with immunosuppression involving T cell arrest and anergy.

1 2D Structure

Indoximod

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R)-2-amino-3-(1-methylindol-3-yl)propanoic acid

2.1.2 InChI

InChI=1S/C12H14N2O2/c1-14-7-8(6-10(13)12(15)16)9-4-2-3-5-11(9)14/h2-5,7,10H,6,13H2,1H3,(H,15,16)/t10-/m1/s1

2.1.3 InChI Key

ZADWXFSZEAPBJS-SNVBAGLBSA-N

2.1.4 Canonical SMILES

CN1C=C(C2=CC=CC=C21)CC(C(=O)O)N

2.1.5 Isomeric SMILES

CN1C=C(C2=CC=CC=C21)C[C@H](C(=O)O)N

2.2 Other Identifiers

2.2.1 UNII

TX5CYN1KMZ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-methyl-dl-trp

2. 1-methyltryptophan

2.3.2 Depositor-Supplied Synonyms

1. 1-methyl-d-tryptophan

2. 110117-83-4

3. D-1mt

4. D-tryptophan, 1-methyl-

5. D-1-methyltryptophan

6. Indoximod (nlg-8189)

7. 1-methyltryptophan

8. D-(+)-1-methyltryptophan

9. Nlg-8189

10. (2r)-2-amino-3-(1-methylindol-3-yl)propanoic Acid

11. (r)-2-amino-3-(1-methyl-1h-indol-3-yl)propanoic Acid

12. 1-methyltryptophan, D-

13. Tx5cyn1kmz

14. Nsc-721782

15. (2r)-2-amino-3-(1-methyl-1h-indol-3-yl)propanoic Acid

16. 1-mt

17. D-l-methyltryptophan

18. D-trp(me)-oh

19. Unii-tx5cyn1kmz

20. Indoximod [usan:inn]

21. Mfcd00274271

22. (2r)-2-azaniumyl-3-(1-methylindol-3-yl)propanoate

23. Indoximod [usan]

24. Nlg 8189

25. 1-methyl-d-tryptophane

26. Indoximod [inn]

27. Indoximod (usan/inn)

28. D-tryptophen, 1-methyl-

29. Indoximod [who-dd]

30. Schembl934800

31. 1-methyl-d-tryptophan, 95%

32. Chembl571209

33. Gtpl8226

34. Zinc39102

35. Dtxsid40911500

36. Indoximod (nlg-8189 Pound(c)

37. Amy22762

38. Bdbm50207089

39. Nsc721782

40. S7756

41. Akos015850753

42. Akos015898463

43. Ccg-266709

44. Cs-4941

45. Db12827

46. Nsc 721782

47. Smp2_000028

48. Ncgc00346842-01

49. Ac-32784

50. As-15999

51. Hy-16724

52. 1-methyl-d-tryptophan (h-d-trp(me)-oh)

53. Db-002380

54. Nlg-8189; D1mt; 1-methyl-d-tryptophan

55. A14397

56. D10640

57. F20545

58. A802144

59. J-002381

60. Brd-k93255255-001-01-3

61. Q27078057

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₄N₂O₂
Molecular Weight	218.25 g/mol
XLogP3	-1.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	218.105527694 g/mol
Monoisotopic Mass	218.105527694 g/mol
Topological Polar Surface Area	68.2 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	270
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1