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Mimosine

Mimosine structure

CAS No:
500-44-7
Formula:
C8H10N2O4
Chemical Name:
Mimosine
Synonyms:
1(4H)-Pyridinepropanoic acid,α-amino-3-hydroxy-4-oxo-,(αS)-;Mimosine;1(4H)-Pyridinepropanoic acid,α-amino-3-hydroxy-4-oxo-,(S)-;(αS)-α-Amino-3-hydroxy-4-oxo-1(4H)-pyridinepropanoic acid;Leucaenine;Leucaenol;Leucenol;Leucenine;L-Mimosine;Mimosin;NSC 69188;27678-82-6
Categories:
Natural Products > Alkaloids

Description

light tan to pink crystalline powder

Solid

L-mimosine is an L-alpha-amino acid that is propionic acid substituted by an amino group at position 2 and a 3-hydroxy-4-oxopyridin-1(4H)-yl group at position 3 (the 2S-stereoisomer). It a non-protein plant amino acid isolated from Mimosa pudica. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor and a plant metabolite. It is a non-proteinogenic L-alpha-amino acid and a member of 4-pyridones. It derives from a propionic acid. It is a conjugate acid of a L-mimosine(1-). It is a tautomer of a L-mimosine zwitterion.|Mimosine is an antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca.|3-Hydroxy-4-oxo-1(4H)-pyridinealanine. An antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca.

Mimosine Basic Attributes

Molecular Weight：

198.18

Exact Mass：

198.18

EC Number：

207-905-1

UNII：

Z46B1LUI5N

Color/Form：

CRYSTALS FROM WATER|TABLETS FROM WATER

HScode：

29333990

Characteristics

PSA：

104

XLogP3：

-2.5

Appearance：

Solid

Density：

1.544g/cm3

Melting Point：

225 °C

Boiling Point：

428.6ºC at 760mmHg

Flash Point：

213ºC

Refractive Index：

1.645

Water Solubility：

1.31e+01 g/L

Specific rotation：

SPECIFIC OPTICAL ROTATION: -21 DEG @ 22 °C/D (WATER, C= 0.5); MAX ABSORPTION (WATER): 215 NM (LOG E= 4.6); 280 NM (LOG E= 4.6)

Collision Cross Section：

143.47 Å² [M+H]+ [CCS Type: DT, Method: stepped-field]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

20/21/22

safety instructions：

22-36

Marks：

Precautionary statement(s)：

P280

Hazard Statements：

H302-H312-H332

Toxicity

Protein Binding：

>99.5%

Natural Pollution Sources：

LEUCAENA LEUCOCEPHALA...A LEGUMINOUS SHRUB FOUND IN MANY TROPICAL REGIONS, IS OF CONSIDERABLE VALUE AS A FOOD FOR CATTLE AND SHEEP, AS IT IS DROUGHT-RESISTANT, WILL GROW IN POOR SOIL, AND HAS A HIGH PROTEIN CONTENT. IT CONTAINS...THE AMINO ACID MIMOSINE (ALSO FOUND IN MIMOSA PUDICA) WHICH ACTS AS A DEPILATORY AGENT... /MIMOSINE/

Drug Information

Pharmacology：

Mimosine inhibits DNA synthesis at the level of elongation of nascent chains by altering deoxyribonucleotide metabolism. It arrests the cell cycle in the late G(1) phase.

Metabolism/Metabolites：

EXPERIMENTAL POISONING OF SHEEP HAS SHOWN THAT MIMOSINE IS LARGELY BROKEN DOWN IN THE RUMEN TO 3,4-DIHYDROXYPYRIDINE, AND EXCRETED AS SUCH. /MIMOSINE/

Mechanism of Action：

Mimosine causes inhibition of DNA replication, changes in the progression of the cells in the cell cycle, and apoptosis. Mimosine appears to introduce breaks into DNA. Mimosine is an iron/zinc chelator. Iron depletion induces DNA double-strand breaks in treated cells, and activates a DNA damage response that results in focal phosphorylation of histones. This leads to inhibition of DNA replication and/or DNA elongation. Some studies indicate that mimosine prevents the initiation of DNA replication, whereas other studies indicate that mimosine disrupts elongation of the replication fork by impairing deoxyribonucleotide synthesis by inhibiting the activity of the iron-dependent enzyme ribonucleotide reductase and the transcription of the cytoplasmic serine hydroxymethyltransferase gene (SHMT). Inhibition of serine hydroxymethyltransferase is moderated by a zinc responsive unit located in front of the SHMT gene.

MeSH Entry Terms：

Leucaenine

Mimosine Use and Manufacturing

Methods of Manufacturing

ISOLN FROM LEUCENA GLAUCA (WILLD) BENTH, LEGUMINOSAE: RENZ, Z PHYSIOL CHEM 244, 153 (1936); MASCRE, COMPT REND 204, 890 (1937). /MIMOSINE/

Uses

DEPILATORY AGENT

Laboratory Methods：

MIMOSINE IN EXCRETA & SERUM DETERMINED BY ION EXCHANGE CHROMATOGRAPHY.

Computed Properties

Molecular Weight:198.18
XLogP3:-3.5
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:198.06405680
Monoisotopic Mass:198.06405680
Topological Polar Surface Area:104
Heavy Atom Count:14
Complexity:321
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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L-Mimosine

CAS No.: 500-44-7

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Guide of Mimosine

Description
Basic Attributes
Characteristics
Safety Information
Toxicity
Drug Information
Use and Manufacturing
Computed Properties
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