You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:08 UTC
Secondary Accession Numbers
  • HMDB15188
Metabolite Identification
Common NameMimosine
DescriptionMimosine is only found in individuals that have used or taken this drug. It is an antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca. [PubChem]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.
(S)-2-Amino-3-(3-hydroxy-4-oxo-4H-pyridin-1-yl)propanoic acidGenerator
Chemical FormulaC8H10N2O4
Average Molecular Weight198.176
Monoisotopic Molecular Weight198.064056818
IUPAC Name(2S)-2-amino-3-(3-hydroxy-4-oxo-1,4-dihydropyridin-1-yl)propanoic acid
Traditional Namemimosine
CAS Registry Number500-44-7
InChI Identifier
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
  • L-alpha-amino acid
  • Dihydropyridine
  • Hydroxypyridine
  • Hydropyridine
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Amino acid
  • Cyclic ketone
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

Biological location:


Industrial application:

Physical Properties
Experimental Properties
Melting Point228 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility13.1 g/LNot Available
LogP-2.5Not Available
Predicted Properties
Water Solubility13.1 g/LALOGPS
pKa (Strongest Acidic)1.94ChemAxon
pKa (Strongest Basic)8.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.86 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.66 m³·mol⁻¹ChemAxon
Polarizability18.2 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fmi-3900000000-bb110a21987d7171e5d0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00gi-9652000000-0c3fa7766f970282f998Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6t-1900000000-d4b420c6ab7e4090ba98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-5900000000-8d371af9d194b02ebfacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-551ced305fa27ac63ef1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-df7fdf320b76d3658905Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-1900000000-e74701d243ce8e114551Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-9000000000-f4afc202a2e71b5e27f2Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01055 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01055 details
Abnormal Concentrations
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01055
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00001383
Chemspider ID389405
KEGG Compound IDC04771
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMimosine
METLIN IDNot Available
PubChem Compound440473
PDB IDNot Available
ChEBI ID29063
Food Biomarker OntologyNot Available
VMH IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available


General function:
Involved in oxidoreductase 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 to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
Uniprot ID:
Molecular weight:
  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. [PubMed:15577244 ]
  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. [PubMed:16750372 ]
  3. Sugumaran M: Tyrosinase catalyzes an unusual oxidative decarboxylation of 3,4-dihydroxymandelate. Biochemistry. 1986 Aug 12;25(16):4489-92. [PubMed:3094574 ]
  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. [PubMed:6234942 ]
General function:
Involved in catalytic activity
Specific function:
Interconversion of serine and glycine.
Gene Name:
Uniprot ID:
Molecular weight:
  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. [PubMed:10766749 ]
  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. [PubMed:11936838 ]
  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. [PubMed:15531579 ]
  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. [PubMed:8576220 ]
General function:
Involved in chemokine activity
Specific function:
Chemotactic factor that attracts monocytes and basophils but not neutrophils or eosinophils. Augments monocyte anti-tumor activity. Has been implicated in the pathogenesis of diseases characterized by monocytic infiltrates, like psoriasis, rheumatoid arthritis or atherosclerosis. May be involved in the recruitment of monocytes into the arterial wall during the disease process of atherosclerosis
Gene Name:
Uniprot ID:
Molecular weight:
  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. [PubMed:11936838 ]
  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. [PubMed:15698514 ]