1-Methyl-D-tryptophan 1-甲基-D-色氨酸
CAS 110117-83-4 MFCD00274271
化学结构图
SMILES: Cn1cc(C[C@@H](N)C(=O)O)c2ccccc21
化学属性
| Mol. Formula | C12H14N2O2 |
|---|---|
| Mol. Weight | 218.25 |
| Melting Point | 242-245 °C (lit.) |
| Appearance | White to off-white solid powder |
| Solubility | Soluble in DMSO, not in water |
别名和识别编码
| Chemical Name | 1-Methyl-D-tryptophan |
|---|---|
| MDL Number | MFCD00274271 |
| PubChem Substance ID | 24868706 |
| Synonym | 1-甲基-D-色氨酸 Indoximod; NLG8189; NLG 8189; NLG-8189; D1MT; 1-methyl-D-tryptophan. |
| Chemical Name Translation | 1-甲基-D-色氨酸 |
| LabNetwork Molecule ID | LN00238205 |
| CAS Number | 110117-83-4 |
| Formula | C12H14N2O2 |
| IUPAC Name | (R)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid |
| InChIKey | ZADWXFSZEAPBJS-SNVBAGLBSA-N |
| 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 |
| Canonical SMILES | N[C@H](CC1=CN(C)C2=CC=CC=C12)C(O)=O |
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分类
- {SNA} Amino Acid Derivatives, Chemical Biology, Chemical Synthesis, Peptide Chemistry, Tryptophan
- {SNA} Amino Acids & Derivatives, Chemical Biology, Chemical Synthesis, Peptide Chemistry, Tryptophan
产品应用
- Indoximod, also known as NLG8189 and D-1MT, is a methylated tryptophan with anti-immunosuppressive activity. 1-methyl-d-tryptophan 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.
相关文献及参考
- [1]. Hou DY, et al. Inhibition of indoleamine 2,3-dioxygenase in dendritic cells by stereoisomers of 1-methyl-tryptophancorrelates with antitumor responses. Cancer Res. 2007 Jan 15;67(2):792-801.
