SMB00930
5-Methoxy-L-tryptophan
98-102%
Synonym(s):
5-Methoxy-L-tryptophan, L-2-Amino-3-(5-methoxyindolyl)propionic acid
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About This Item
Empirical Formula (Hill Notation):
C12H14N2O3
CAS Number:
Molecular Weight:
234.25
UNSPSC Code:
12352209
NACRES:
NA.26
Quality Level
assay
98-102%
form
solid
optical activity
[α]20/D -30 to -28° in water
color
off-white to light yellow
storage temp.
2-8°C
SMILES string
[N+H3][C@@H](Cc1c2c([nH]c1)ccc(c2)OC)C(=O)[O-]
InChI
1S/C12H14N2O3/c1-17-8-2-3-11-9(5-8)7(6-14-11)4-10(13)12(15)16/h2-3,5-6,10,14H,4,13H2,1H3,(H,15,16)/t10-/m0/s1
InChI key
KVNPSKDDJARYKK-JTQLQIEISA-N
General description
5-Methoxy-L-tryptophan is a L-tryptophan metabolite that exhibits anti-inflammatory and tumor-suppressing activities. 5-Methoxy-L-tryptophan is synthesized by tryptophan hydroxylase (TPH) and hydroxyindole O-methyltransferase (HIOMT). A recent study indicates 5-methoxytryptophan as a biomarker of the progression of chronic kidney disease (CKD). Its levels decrease during disease and treatment with 5-methoxytryptophan ameliorates kidney fibrosis in mice model of CKD. 5-Methoxytryptophan appears to inhibit IκB/NFκB signaling and enhances Keap1/Nrf2 signaling in mice models of unilateral ureteral obstruction.
Application
5-Methoxy-L-tryptophan finds application in cell biology, biochemical and metabolomics research.
Features and Benefits
- Can be used in Metabolomics and Biochemical research
- High-quality compound suitable for multiple research applications
Other Notes
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signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
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Hua-Ling Chen et al.
The Journal of biological chemistry, 293(28), 11131-11142 (2018-05-26)
5-Methoxytryptophan (5-MTP) is a tryptophan metabolite with recently discovered anti-inflammatory and tumor-suppressing activities. Its synthesis is catalyzed by a hydroxyindole O-methyltransferase (HIOMT)-like enzyme. However, the exact identity of this HIOMT in human cells remains unclear. Human HIOMT exists in several
Huei-Hsuan Cheng et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(33), 13231-13236 (2012-08-02)
Cyclooxygenase-2 (COX-2) expression is induced by mitogenic and proinflammatory factors. Its overexpression plays a causal role in inflammation and tumorigenesis. COX-2 expression is tightly regulated, but the mechanisms are largely unclear. Here we show the control of COX-2 expression by
Dan-Qian Chen et al.
Nature communications, 10(1), 1476-1476 (2019-04-02)
Early detection and accurate monitoring of chronic kidney disease (CKD) could improve care and retard progression to end-stage renal disease. Here, using untargeted metabolomics in 2155 participants including patients with stage 1-5 CKD and healthy controls, we identify five metabolites
Global Trade Item Number
| SKU | GTIN |
|---|---|
| SMB00930-100MG | 04061841846840 |
| SMB00930-500MG | 04061841846871 |
| SMB00930-1G | 04061841846857 |
| SMB00930-250MG | 04061841846864 |