NAV

Mimosine

Identification

Generic Name
Mimosine
DrugBank Accession Number
DB01055
Background

Mimosine is an antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 198.176
Monoisotopic: 198.064056818
Chemical Formula
C8H10N2O4
Synonyms
  • (L)-Mimosine
  • (S)-2-amino-3-(3-hydroxy-4-oxo-4H-pyridin-1-yl)propanoate
  • L-Mimosine
  • Leucaenine
  • Leucaenol
  • Leucenine
  • Leucenol
  • Mimosin
External IDs
  • NSC-69188
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Pharmacology

Indication

Not Available

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Pharmacodynamics

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.

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.

TargetActionsOrganism
ASerine hydroxymethyltransferase, cytosolic
inhibitor
Humans
AC-C motif chemokine 2
inhibitor
Humans
UTyrosinase
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

>99.5%

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
Hydroxypyridines / Dihydropyridines / Vinylogous amides / Heteroaromatic compounds / Cyclic ketones / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds
show 3 more
Substituents
Amine / Amino acid / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxylic acid / Cyclic ketone / Dihydropyridine / Heteroaromatic compound / Hydrocarbon derivative
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid (CHEBI:29063)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
Z46B1LUI5N
CAS number
500-44-7
InChI Key
WZNJWVWKTVETCG-YFKPBYRVSA-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
IUPAC Name
(2S)-2-amino-3-(3-hydroxy-4-oxo-1,4-dihydropyridin-1-yl)propanoic acid
SMILES
N[C@@H](CN1C=CC(=O)C(O)=C1)C(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0015188
KEGG Compound
C04771
PubChem Compound
440473
PubChem Substance
46505895
ChemSpider
389405
BindingDB
50198715
ChEBI
77689
ChEMBL
CHEMBL245416
ZINC
ZINC000000902159
Therapeutic Targets Database
DNC000947
PharmGKB
PA164752445
PDBe Ligand
MMS
Wikipedia
Mimosine
PDB Entries
5m8n / 5m8r
MSDS
Download (61 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)228 dec °CPhysProp
logP-2.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility13.1 mg/mLALOGPS
logP-2.4ALOGPS
logP-3Chemaxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.94Chemaxon
pKa (Strongest Basic)9.05Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area103.86 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity48.66 m3·mol-1Chemaxon
Polarizability18.2 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6591
Blood Brain Barrier-0.9388
Caco-2 permeable-0.7696
P-glycoprotein substrateSubstrate0.653
P-glycoprotein inhibitor INon-inhibitor0.979
P-glycoprotein inhibitor IINon-inhibitor0.9717
Renal organic cation transporterNon-inhibitor0.8735
CYP450 2C9 substrateNon-substrate0.8796
CYP450 2D6 substrateNon-substrate0.8236
CYP450 3A4 substrateNon-substrate0.7208
CYP450 1A2 substrateNon-inhibitor0.9115
CYP450 2C9 inhibitorNon-inhibitor0.9388
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.953
CYP450 3A4 inhibitorNon-inhibitor0.9881
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9919
Ames testNon AMES toxic0.6831
CarcinogenicityNon-carcinogens0.9491
BiodegradationNot ready biodegradable0.818
Rat acute toxicity2.1155 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9793
hERG inhibition (predictor II)Non-inhibitor0.8617
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0fmi-3900000000-bb110a21987d7171e5d0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udj-0900000000-be56e5f37800cfc3baa7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dj-0900000000-41a24f2fe242ffccfd62
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-022i-3900000000-2e26c8acf9cbf3251c4f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dr-4900000000-674a7de87d9cae4b6c36
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-9300000000-da93b74f7699ab1a2f7a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0k97-9100000000-014e469225cf8f46ee89
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-147.4488523
predicted
DarkChem Lite v0.1.0
[M-H]-147.2460523
predicted
DarkChem Lite v0.1.0
[M-H]-147.2624523
predicted
DarkChem Lite v0.1.0
[M-H]-138.77718
predicted
DeepCCS 1.0 (2019)
[M+H]+145.5367523
predicted
DarkChem Lite v0.1.0
[M+H]+148.9390904
predicted
DarkChem Standard v0.1.0
[M+H]+145.5297523
predicted
DarkChem Lite v0.1.0
[M+H]+141.17274
predicted
DeepCCS 1.0 (2019)
[M+Na]+145.3543523
predicted
DarkChem Lite v0.1.0
[M+Na]+145.0997523
predicted
DarkChem Lite v0.1.0
[M+Na]+145.5351523
predicted
DarkChem Lite v0.1.0
[M+Na]+147.36754
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Serine hydroxymethyltransferase, cytosolic
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine binding
Specific Function
Interconversion of serine and glycine.
Gene Name
SHMT1
Uniprot ID
P34896
Uniprot Name
Serine hydroxymethyltransferase, cytosolic
Molecular Weight
53082.18 Da
References
  1. Oppenheim EW, Nasrallah IM, Mastri MG, Stover PJ: Mimosine is a cell-specific antagonist of folate metabolism. J Biol Chem. 2000 Jun 23;275(25):19268-74. [Article]
  2. Conti P, Frydas S, Reale M, Barbacane RC, Di Gioacchino M, Felaco M, Trakatellis A: Inhibition of MCP-1 and MIP-2 transcription and translation by mimosine in muscle tissue infected with the parasite Trichinella spiralis. Mol Cell Biochem. 2002 Jan;229(1-2):129-37. [Article]
  3. Perry C, Sastry R, Nasrallah IM, Stover PJ: Mimosine attenuates serine hydroxymethyltransferase transcription by chelating zinc. Implications for inhibition of DNA replication. J Biol Chem. 2005 Jan 7;280(1):396-400. Epub 2004 Nov 4. [Article]
  4. Lin HB, Falchetto R, Mosca PJ, Shabanowitz J, Hunt DF, Hamlin JL: Mimosine targets serine hydroxymethyltransferase. J Biol Chem. 1996 Feb 2;271(5):2548-56. [Article]
Details2. C-C motif chemokine 2
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Not Available
Specific Function
Not Available
Gene Name
CCL2
Uniprot ID
P13500
Uniprot Name
C-C motif chemokine 2
Molecular Weight
11024.87 Da
References
  1. Conti P, Frydas S, Reale M, Barbacane RC, Di Gioacchino M, Felaco M, Trakatellis A: Inhibition of MCP-1 and MIP-2 transcription and translation by mimosine in muscle tissue infected with the parasite Trichinella spiralis. Mol Cell Biochem. 2002 Jan;229(1-2):129-37. [Article]
  2. Frydas S, Papaioannou N, Papazahariadou M, Hatzistilianou M, Karagouni E, Trakatelli M, Brellou G, Petrarca C, Castellani ML, Conti P, Riccioni G, Patruno A, Grilli A: Inhibition of MCP-1 and MIP-2 chemokines in murine trichinellosis: effect of the anti-inflammatory compound L-mimosine. Int J Immunopathol Pharmacol. 2005 Jan-Mar;18(1):85-94. [Article]
Details3. Tyrosinase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Protein homodimerization activity
Specific Function
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA ...
Gene Name
TYR
Uniprot ID
P14679
Uniprot Name
Tyrosinase
Molecular Weight
60392.69 Da
References
  1. Ahmad VU, Ullah F, Hussain J, Farooq U, Zubair M, Khan MT, Choudhary MI: Tyrosinase inhibitors from Rhododendron collettianum and their structure-activity relationship (SAR) studies. Chem Pharm Bull (Tokyo). 2004 Dec;52(12):1458-61. [Article]
  2. Khan KM, Mughal UR, Khan MT, Zia-Ullah, Perveen S, Choudhary MI: Oxazolones: new tyrosinase inhibitors; synthesis and their structure-activity relationships. Bioorg Med Chem. 2006 Sep 1;14(17):6027-33. Epub 2006 Jun 5. [Article]
  3. Sugumaran M: Tyrosinase catalyzes an unusual oxidative decarboxylation of 3,4-dihydroxymandelate. Biochemistry. 1986 Aug 12;25(16):4489-92. [Article]
  4. Woolery GL, Powers L, Winkler M, Solomon EI, Lerch K, Spiro TG: Extended X-ray absorption fine structure study of the coupled binuclear copper active site of tyrosinase from Neurospora crassa. Biochim Biophys Acta. 1984 Jul 31;788(2):155-61. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:48