Indoximod
Grundinformationen
- CAS
110117-83-4- Standard-SMILES
Cn1cc(C[C@@H](N)C(=O)O)c2ccccc21- InChIKey
ZADWXFSZEAPBJS-SNVBAGLBSA-N- Summenformel
- C12H14N2O2
- Durchschnittliche Molmasse
- 218,25 g/mol
- Monoisotopische Masse
- 218,10552769
Überblick
Indoximod is an indolyl carboxylic acid.
Namen und Bezeichner
- Bevorzugter Name
- Indoximod
- IUPAC
- (2R)-2-amino-3-(1-methylindol-3-yl)propanoic acid
- Englischer Name
- 1-METHYL-D-TRYPTOPHAN
- Summenformel
- C12H14N2O2
- Molmasse
- 218.25
Namen und Synonyme
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
Weitere Namen anzeigen
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
Datenbank-Bezeichner
- CAS
110117-83-4- PubChem CID
- 405012
- DTXSID
DTXSID40911500- ChEMBL
CHEMBL571209- ChEBI
CHEBI:230682- UNII
- TX5CYN1KMZ
- Nikkaji
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -1,3
- Polarare Oberfläche (TPSA)
- 68,3 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 16
- Formalladung
- 0
- Komplexität
- 270
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Physikochemische Eigenschaften
- Schmelzpunkt
- 242 · 242-245 °C(lit.)
- Siedepunkt
- 429.3 · 429.3±35.0 °C(Predicted)
- Dichte
- 1.28 · 1.28
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- Löslichkeit
- Soluble in DMSO (greater than 25 mg/ml).
- pka
- 2.26 · 2.26±0.10(Predicted)
- Aggregatzustand
- White to light brown crystalline powder.
- Farbe
- White
- Wasserlöslichkeit
- 5 mM · Soluble to 5 mM in water with gentle warming
- Stabilität
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
- Major Application
- peptide synthesis
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 3
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Anwendungen
BeschreibungIndoleamine 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.
VerwendenIndoleamine 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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