Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H14N2.ClH |
| Molecular Weight | 210.703 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN(C)CC1=CNC2=C1C=CC=C2
InChI
InChIKey=XJYDLXFETVVFTN-UHFFFAOYSA-N
InChI=1S/C11H14N2.ClH/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11;/h3-7,12H,8H2,1-2H3;1H
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C11H14N2 |
| Molecular Weight | 174.2423 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Gramine (aka donaxine) is a naturally occurring indole alkaloid that can be found in several plant species. It is toxic to many organisms and may be a natural defense mechanism for these plants. Gramine has been found to act as an agonist of the adiponectin receptor 1 (AdipoR1) which plays an important role in the suppression of metabolic disorders that can result in type 2 diabetes, obesity, and atherosclerosis.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q96A54 Gene ID: 51094.0 Gene Symbol: ADIPOR1 Target Organism: Homo sapiens (Human) |
3.6 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Response of animals to dietary gramine. II. Effects of feeding high-gramine yellow lupin seeds on reproductive performance of rats and on selected hematological and biochemical parameters in offspring. | 2001 |
|
| Response of animals to dietary gramine. I. Performance and selected hematological, biochemical and histological parameters in growing chicken, rats and pigs. | 2001 |
|
| Diastereoselective reactions in glycine templates containing an ent-ardeemin fragment. | 2002 Apr 5 |
|
| Rapid route to 3,4-substituted indoles via a directed ortho metalation-retro-Mannich sequence. | 2002 Mar 7 |
|
| Activation of MMP-2, cleavage of matrix proteins, and adherens junctions during a snake venom metalloproteinase-induced endothelial cell apoptosis. | 2003 Aug 1 |
|
| Serotonin regulates repolarization of the C. elegans pharyngeal muscle. | 2003 Jan |
|
| Convenient synthesis of 5,6,11,12,17,18- hexahydrocyclononal[1,2-b:4,5-b':7,8-b'']triindole, a novel phytoestrogen. | 2003 Jan 10 |
|
| N1-benzenesulfonylgramine and N1-benzenesulfonylskatole: novel 5-HT6 receptor ligand templates. | 2003 Oct 6 |
|
| Asymmetric, stereocontrolled total synthesis of paraherquamide A. | 2003 Oct 8 |
|
| Synthesis of N-protected staurosporinones. | 2007 Mar 16 |
|
| Oxidation of suspected N-nitrosodimethylamine (NDMA) precursors by ferrate (VI): kinetics and effect on the NDMA formation potential of natural waters. | 2008 Jan |
|
| Annotation and expression of carboxylesterases in the silkworm, Bombyx mori. | 2009 Nov 24 |
|
| Classification of rice (Oryza sativa L. Japonica nipponbare) immunophilins (FKBPs, CYPs) and expression patterns under water stress. | 2010 Nov 18 |
Sample Use Guides
Three doses (50 mg/kg, 100 mg/kg, and 150 mg/kg) were administered orally to Swiss albino mice for 48 h to study the genotoxic activity in micronucleus assay as well as any chromosomal aberration. Gramine at the given dose lacks mutagenicity as well as found to possess antimutagenic efficacy.
Route of Administration:
Oral
Human MCF-7 and MDA-MB-231 cells were maintained in DMEM containing 10% fetal bovine serum and supplied with 1% penicillin/streptomycin. Cells were incubated at37 deg-C in a 5% CO2 atmosphere. Cells were grown to 80% confluence and aliquoted into 100 mm dishes in serum-free media. Cells were allowed to attach overnight and 5 micro-L culture media containing gramine was added. Cells were incubated with 20 µM to 1.2 nM gramine for 72 hours after which proliferation was evaluated using CellTilter-Blue reagent. Gramine inhibited the growth of MDA-MB-231 and MCF-7 cells with IC50 values of 15.3 and 10.6 micro-M respectively.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 03:19:02 GMT 2023
by
admin
on
Sat Dec 16 03:19:02 GMT 2023
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| Record UNII |
WG4YAO21YD
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| Record Status |
Validated (UNII)
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| Record Version |
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6454248
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DTXSID60210709
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m5839
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6170-37-2
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