(2S)-2-amino-3-(3-hydroxy-4-oxo-1,4-dihydropyridin-1-yl)propanoic acid

• ChemBase ID: 926
• Molecular Formular: C8H10N2O4
• Molecular Mass: 198.176
• Monoisotopic Mass: 198.06405681
• SMILES: OC(=O)[C@@H](N)Cn1cc(O)c(=O)cc1
• Canonical SMILES: OC(=O)[C@H](Cn1ccc(=O)c(c1)O)N
• InChI: InChI=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
• InChIKey: WZNJWVWKTVETCG-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(3-hydroxy-4-oxo-1,4-dihydropyridin-1-yl)propanoic acid
• IUPAC Traditional name: mimosine
• Synonyms: (S)-α-Amino-β-[1-(3-hydroxy-4-oxopyridine)]propionic acid; L-Mimosine from Koa hoale seeds; β-[N-(3-Hydroxy-4-pyridone)-α-aminopropionic acid; L-MIMOSINE; L-Mimosine; Leucaenine; Leucaenol; Leucenine; Leucenol; Mimosin; Mimosine

Database IDs

• CAS Number: 500-44-7
• EC Number: 207-905-1
• MDL Number: MFCD00075909
• PubChem SID: 46505895; 160964389; 24896541
• PubChem CID: 440473

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.9351499
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -2.959101
• LogD (pH = 7.4): -2.9720697
• Log P: -2.9591975
• Molar Refractivity: 48.6582 cm^3
• Polarizability: 18.249966 Å^3
• Polar Surface Area: 103.86 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.43
• LOG S: -1.18
• Solubility (Water): 1.31e+01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -2.5

Safety Information

• Storage Condition: 2-8°C
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 22-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98%; ≥98%

DETAILS

MP Biomedicals - 02159973

Purity: >98%
A rare amino acid from plants which reversibly blocks the G1 phase of the cell cycle. Deoxyhypusine hydroxylation inhibitor that subsequently inhibits eukaryote initiation factor 5-A.

DrugBank - DB01055

• Drug Groups: approved
• Description: 3-Hydroxy-4-oxo-1(4H)-pyridinealanine. An antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca. [PubChem]
• 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.
• Affected Organisms: Humans and other mammals
• Protein Binding: >99.5%
• External Links: Wikipedia

Sigma Aldrich - M0253

Biochem/physiol Actions
L-Mimosine is a plant amino acid and potential inhibitor of the cell cycle giving rise to growth arrest in G1-phase. An iron chelator that inhibits DNA replication in mammalian cells. Has been shown to have apoptotic activity in xenotransplanted human pancreatic cancer. L-Mimosine is also used as a hypoxia-mimetic agent to stabilize Hypoxia Inducible Factor 1 (HIF-1). L-Mimosine stabilizes HIF-1 through the inhibition of Prolyl Hydroxylases (PHDs) which target HIF-1 through degradation. The mechanism of inhibition is likely through the chelation of Fe2+ bound to the active site of PHD which is required for enzymatic activity.

REFERENCES

• Hanauske-Abel, H.M., et al., Biochim. Biophys. Acta , 1221 : 115 (1994).