Basic information
- CAS
110117-83-4- Standard SMILES
Cn1cc(C[C@@H](N)C(=O)O)c2ccccc21- InChIKey
ZADWXFSZEAPBJS-SNVBAGLBSA-N- Molecular formula
- C12H14N2O2
- Average molar mass
- 218.25 g/mol
- Monoisotopic mass
- 218.10552769
Overview
Indoximod is an indolyl carboxylic acid.
Names & identifiers
- Preferred name
- Indoximod
- IUPAC
- (2R)-2-amino-3-(1-methylindol-3-yl)propanoic acid
- English name
- 1-METHYL-D-TRYPTOPHAN
- Molecular formula
- C12H14N2O2
- Molecular weight
- 218.25
Names & synonyms
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
Show more names
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
Database identifiers
- CAS
110117-83-4- PubChem CID
- 405012
- DTXSID
DTXSID40911500- ChEMBL
CHEMBL571209- ChEBI
CHEBI:230682- UNII
- TX5CYN1KMZ
- Nikkaji
Properties
Computed structural properties
- XLogP
- -1.3
- Topological polar surface area
- 68.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 270
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 242 · 242-245 °C(lit.)
- alpha
- 12.4 o · 12.4o (C = 2 IN ACETIC ACID)
- Boiling point
- 429.3 · 429.3±35.0 °C(Predicted)
- Density
- 1.28 · 1.28
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Soluble in DMSO (greater than 25 mg/ml).
- pka
- 2.26 · 2.26±0.10(Predicted)
- form
- White to light brown crystalline powder.
- color
- White
- optical activity
- 22 · [α]22/D +12.4°, c = 2 in acetic acid
- Water Solubility
- 5 mM · Soluble to 5 mM in water with gentle warming
- Stability
- 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.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
DescriptionIndoleamine 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.
UsesIndoleamine 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.
Uses1-Methyl-D-tryptophan is used in biological studies to determine the effect of IDO2 enzyme (indoleamine-(2,3)-dioxygenase) activity and IDO2-mediated arrest of human T cell proliferation. It reverses IDO-mediated immune suppression
Upstream & downstream products
Upstream raw materials
Related reactions
2 records
Compound notes
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