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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:
25197-96-0
Molecular Weight:
234.25
UNSPSC Code:
12352209
NACRES:
NA.26

Key Documents

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Product Name

5-Methoxy-L-tryptophan, 98-102%

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

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

Quality Level

100

Related Categories

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

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.

Other Notes

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pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

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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Certificates of Analysis (COA)

Lot/Batch Number
0000520170
0000520173
0000520170
0000520173
0000520169

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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

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