L-mimosine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for L-mimosine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the L-mimosine?

The molecule L-mimosine presents a molecular formula of C8H10N2O4 and its IUPAC name is (2S)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoic acid.

L-mimosine is a molecule that has been shown to have a variety of potential therapeutic applications. In preclinical studies, L-mimosine has demonstrated anti-cancer, anti-inflammatory, and anti-angiogenic activity. Additionally, L-mimosine has been shown to promote nerve regeneration and protect against neurodegenerative diseases..

L-mimosine was first isolated from the plant Mimosa pudica in the early 1970s. Since then, a great deal of research has been conducted on the molecule in an effort to better understand its structure and function. L-mimosine is a non-protein amino acid that is structurally similar to tryptophan. It is thought to exert its therapeutic effects by modulating a variety of cellular signaling pathways..

Preclinical studies have shown that L-mimosine has potent anti-cancer activity. In one study, L-mimosine was shown to inhibit the growth of human breast cancer cells in vitro. Additionally, L-mimosine was shown to induce apoptosis in these cancer cells. These findings suggest that L-mimosine may be a promising new treatment for breast cancer..

L-mimosine has also been shown to have anti-inflammatory activity. In a mouse model of inflammatory bowel disease, L-mimosine was shown to reduce inflammation and improve disease symptoms. Additionally, L-mimosine was shown to inhibit the production of pro-inflammatory cytokines. These findings suggest that L-mimosine may be a useful treatment for inflammatory diseases..

L-mimosine has also been shown to have anti-angiogenic activity. In one study, L-mimosine was shown to inhibit the growth of new blood vessels in a mouse model of cancer. Additionally, L-mimosine was shown to reduce the levels of pro-angiogenic factors. These findings suggest that L-mimosine may be a useful treatment for cancer..

L-mimosine has also been shown to promote nerve regeneration. In a mouse model of nerve injury, L-mimosine was shown to promote the regeneration of damaged nerves. Additionally, L-mimosine was shown to improve functional recovery after nerve injury. These findings suggest that L-mimosine may be a useful treatment for nerve damage..

L-mimosine has also been shown to protect against neurodegenerative diseases. In one study, L-mimosine was shown to protect against the development of Alzheimer’s disease in a mouse model. Additionally, L-mimosine was shown to improve cognitive function in these mice. These findings suggest that L-mimosine may be a useful treatment for Alzheimer’s disease..

The findings of these preclinical studies suggest that L-mimosine has a wide range of potential therapeutic applications. However, more research is needed to confirm the efficacy of L-mimosine in humans..

3D structure

Cartesian coordinates

Geometry of L-mimosine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

L-mimosine WZNJWVWKTVETCG-YFKPBYRVSA-N chemical compound 2D structure molecule svg
L-mimosine

 

Molecule descriptors

 
IUPAC name(2S)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoic acid
InChI codeInChI=1S/C8H10N2O4/c9-5(8(13)14)3-10-2-1-6(11)7(12)4-10/h1-2,4-5,12H,3,9H2,(H,13,14)/t5-/m0/s1
InChI KeyWZNJWVWKTVETCG-YFKPBYRVSA-N
SMILESN[C@@H](Cn1ccc(=O)c(O)c1)C(=O)O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (2S)-2-Amino-3-[3-hydroxy-4-oxo-1(4H)-pyridyl]propanoic acid
  • (2S)-2-amino-3-(3-hydroxy-4-oxo-1,4-dihydropyridin-1-yl)propanoic acid
  • (2S)-2-amino-3-(3-hydroxy-4-oxo-1-pyridyl)propanoic acid
  • (2S)-2-amino-3-(3-hydroxy-4-oxopyridin-1(4H)-yl)propanoic acid
  • (2S)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoic acid
  • (2S)-2-azaniumyl-3-(4-hydroxy-3-oxidopyridinium-1-yl)propanoate
  • (L)-MIMOSINE
  • (S)-2-Amino-3-(3-hydroxy-4-oxo-4H-pyridin-1-yl)propanoate
  • (S)-2-Amino-3-(3-hydroxy-4-oxopyridin-1(4H)-yl)propanoic acid
  • (S)-alpha-Amino-3-hydroxy-4-oxo-1(4H)-pyridylpropionic acid
  • 1(4H)-Pyridinepropanoic acid, .alpha.-amino-3-hydroxy-4-oxo-, (.alpha.S)-
  • 1(4H)-Pyridinepropanoic acid, alpha-amino-3-hydroxy-4-oxo-, (S)-
  • 1(4H)-Pyridinepropanoic acid, alpha-amino-3-hydroxy-4-oxo-, (alphaS)-
  • 1-mimosine
  • 3-(3-hydroxy-4-oxopyridin-1(4H)-yl)-L-alanine
  • 500-44-7
  • A14279
  • A853611
  • AB00513825
  • AC-35157
  • AI3-51821
  • AS-56262
  • BDBM50198715
  • BIDD:ER0500
  • BPBio1_000591
  • BSPBio_000537
  • Bio1_000356
  • Bio1_000845
  • Bio1_001334
  • C04771
  • CCG-208235
  • CS-0012957
  • DB01055
  • HMS2096K19
  • HMS3263H18
  • HSDB 3512
  • HY-N0928
  • L-Leucinine
  • L-Mimosine from Koa hoale seeds
  • L-mimosine
  • LP01238
  • Leucaenine
  • Leucaenol
  • Leucenine
  • Leucenol
  • M-7300
  • MFCD00075909
  • Mimosin
  • Mimosine
  • Minosine, L-
  • NCGC00179528-01
  • NCGC00179528-02
  • NCGC00179528-04
  • NCGC00179528-07
  • NCGC00261923-01
  • NSC 69188
  • NSC-69188
  • Prestwick3_000379
  • Q3180669
  • SDCCGSBI-0633809.P001
  • SR-05000002336
  • SR-05000002336-2
  • SR-05000002336-3
  • TRITYLIUMTRIFLATE
  • Z46B1LUI5N
  • s7446
  • starbld0036637

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC902159
  • UNII-Z46B1LUI5N
  • DTXSID401017244
  • CHEMBL245416
  • CHEBI:29063
  • Tox21_501238
  • EINECS 207-905-1
  • SCHEMBL41925

Physico-Chemical properties

IUPAC name(2S)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoic acid
Molecular formulaC8H10N2O4
Molecular weight198.176
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity48.08
LogP-0.3
Topological polar surface area105.6

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.