基本情報
- CAS
110117-83-4- 標準SMILES
Cn1cc(C[C@@H](N)C(=O)O)c2ccccc21- InChIKey
ZADWXFSZEAPBJS-SNVBAGLBSA-N- 分子式
- C12H14N2O2
- 平均分子量
- 218.25 g/mol
- 単同位体質量
- 218.10552769
概要
Indoximod is an indolyl carboxylic acid.
名称と識別子
- 優先名称
- Indoximod
- IUPAC
- (2R)-2-amino-3-(1-methylindol-3-yl)propanoic acid
- 現地名
- 1-メチル-D-トリプトファン
- 英語名
- 1-METHYL-D-TRYPTOPHAN
- 分子式
- C12H14N2O2
- 分子量
- 218.25
名称と別名
1-Methyl-D-tryptophanIndoximod110117-83-4D-Tryptophan, 1-methyl-D-1MTD-1-methyltryptophanD-(+)-1-Methyltryptophan(2R)-2-amino-3-(1-methylindol-3-yl)propanoic acid1-methyltryptophan, d-NSC-721782TX5CYN1KMZNLG-8189
名称をさらに表示
インドキシモドMe-D-Trp1-Me-D-TrpD-Trp(Me)-OHH-D-Trp(1-Me)-OHIndoximod (NLG-8189）1-Methyl-D-tryptophane
indoximodumRefChem:923428MFCD00274271(R)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acidN-1-Methyl-D-tryptophan(2R)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid1MT1-MT
データベース識別子
- CAS
110117-83-4- PubChem CID
- 405012
- DTXSID
DTXSID40911500- ChEMBL
CHEMBL571209- ChEBI
CHEBI:230682- UNII
- TX5CYN1KMZ
- Nikkaji
- J340.643A
物性
構造計算による物性
- XLogP
- -1.3
- 極性表面積
- 68.3 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 3
- 回転可能結合数
- 3
- 重原子数
- 16
- 形式電荷
- 0
- 複雑度
- 270
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
物理化学的性質
- 融点
- 242 · 242-245 °C(lit.)
- 比旋光度
- 12.4 o · 12.4o (C = 2 IN ACETIC ACID)
- 沸点
- 429.3 · 429.3±35.0 °C(Predicted)
- 比重(密度)
- 1.28 · 1.28
- 貯蔵温度
- Keep in dark place,Sealed in dry,Room Temperature
- 溶解性
- DMSO に可溶 (25 mg/ml 以上)。
- 酸解離定数(Pka)
- 2.26 · 2.26±0.10(Predicted)
- 外見
- 白色から淡褐色の結晶性粉末。
- 色
- 白い
- 水溶解度
- 5 mM · Soluble to 5 mM in water with gentle warming
- 安定性
- -20 °C · -20°C の DMSO 溶液で最大 1 か月間保存できます。
- 主な用途
- ペプチド合成
- 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
- InChIKey
- ZADWXFSZEAPBJS-SNVBAGLBSA-N
- SMILES
- C(O)(=O)[C@@H](CC1C2=C(C=CC=C2)N(C)C=1)N
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
安全データ
- wgk
- 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
応用分野
説明Indoleamine 2,3-dioxygenase (IDO) metabolizes tryptophan to kynurenine, leading to the production of NAD+ via the kynurenine pathway. The overexpression of IDO in tumors and tumor-draining lymph nodes induces immune tolerance and enhances tumor growth in vivo. 1-methyl-D-Tryptophan is an inhibitor of IDO (IC50 = 7 μM) that is effective in vivo. In mice, 1-methyl-D-tryptophan prevents T-cell anergy triggered by dendritic cells overexpressing IDO. It augments the antitumor and antiviral immunoresponse of CD8+ T-cells and reduces tumor volume in mice with xenografts overexpressing IDO. 1-methyl-D-Tryptophan, in combination with chemotherapy, causes regression of tumors and prolongs survival. Surprisingly, 1-methyl-D-tryptophan induces the expression of IDO in human ovarian carcinoma SKOV3 cells in culture.
使用Indoleamine 2,3-dioxygenase (IDO) metabolizes tryptophan to kynurenine, leading to the production of NAD+ via the kynurenine pathway. The overexpression of IDO in tumors and tumor-draining lymph nodes induces immune tolerance and enhances tumor growth in vivo. 1-methyl-D-Tryptophan is an inhibitor of IDO (IC50 = 7 μM) that is effective in vivo. In mice, 1-methyl-D-tryptophan prevents T-cell anergy triggered by dendritic cells overexpressing IDO. It augments the antitumor and antiviral immunoresponse of CD8+ T-cells and reduces tumor volume in mice with xenografts overexpressing IDO. 1-methyl-D-Tryptophan, in combination with chemotherapy, causes regression of tumors and prolongs survival. Surprisingly, 1-methyl-D-tryptophan induces the expression of IDO in human ovarian carcinoma SKOV3 cells in culture.
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