Human Metabolome Database Version 3.5

Showing metabocard for Anserine (HMDB00194)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:03 -0700
HMDB ID HMDB00194
Secondary Accession Numbers None
Metabolite Identification
Common Name Anserine
Description This dipeptide is normally absent from human tissues and body fluids, and its appearance there is an artifact of diet (Proc Soc Pediatr Res 134, 1967.) and serum carnosinase deficiency. (OMIM 212200 Link_out) Anserine is present in the skeletal muscle of birds and certain species of mammals, notably the rabbit, rat, and whale, contains anserine. (Proc Soc Pediatr Res 134, 1967) The methyl group of anserine is added to carnosine by the enzyme S-adenosylmethionine: carnosine N-methyltransferase. (J Biol Chem 237:1207, 1962.).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Anserine
  2. beta-Alanyl-N(pai)-methyl-L-histidine
  3. L-Anserine
  4. L-N-b-Alanyl-3-methyl-Histidine
  5. L-N-beta-Alanyl-3-methyl-Histidine
  6. N-b-Alanyl-3-methyl-L-Histidine
  7. N-beta-Alanyl-3-methyl-L-histidine
Chemical Formula C10H16N4O3
Average Molecular Weight 240.259
Monoisotopic Molecular Weight 240.122240398
IUPAC Name (2S)-2-(3-aminopropanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
Traditional IUPAC Name anserine
CAS Registry Number 584-85-0
SMILES CN1C=NC=C1C[C@H](NC(=O)CCN)C(O)=O
InChI Identifier InChI=1S/C10H16N4O3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/m0/s1
InChI Key MYYIAHXIVFADCU-QMMMGPOBSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Peptidomimetics
Sub Class Hybrid Peptides
Other Descriptors
  • Aromatic Heteromonocyclic Compounds
  • zwitterion(ChEBI)
Substituents
  • Alpha Amino Acid Or Derivative
  • Beta Amino Acid Or Derivative
  • Carboxamide Group
  • Carboxylic Acid
  • Imidazole
  • Imidazolyl Carboxylic Acid Derivative
  • N Acyl Alpha Amino Acid
  • N Substituted Alpha Amino Acid
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Carboxylic Acid Amide
Direct Parent Hybrid Peptides
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 226 - 228 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 4.01 g/L ALOGPS
LogP -2.95 ALOGPS
LogP -4.3 ChemAxon
LogS -1.78 ALOGPS
pKa (strongest acidic) 3.44 ChemAxon
pKa (strongest basic) 9.13 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 110.24 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 60.46 ChemAxon
Polarizability 24.23 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Muscle
  • Brain
  • Prostate
Pathways
Name SMPDB Link KEGG Link
Beta-Alanine Metabolism SMP00007 map00410 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
41.0 +/- 10.0 uM Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected and Quantified
16.16 umol/mmol creatinine Adult (>18 years old) Male Comment Normal
  • Shaykhutdino...
Urine Detected and Quantified
7.0 (3.3 -20.0) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
<5.921 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.457 +/- 0.214 uM Elderly (>65 years old) Both Alzheimer's disease
Urine Detected and Quantified 8.0 +/- 5.0 umol/mmol creatinine Adult (>18 years old) Both Alzheimer's disease
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  • Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. Pubmed: 17031479 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB021903
      KNApSAcK ID Not Available
      Chemspider ID 100482 Link_out
      KEGG Compound ID C01262 Link_out
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Anserine Link_out
      NuGOwiki Link HMDB00194 Link_out
      Metagene Link HMDB00194 Link_out
      METLIN ID 5209 Link_out
      PubChem Compound 112072 Link_out
      PDB ID Not Available
      ChEBI ID 18323 Link_out
      References
      Synthesis Reference Yudaev, N. A. Biosynthesis of anserine. Doklady Akademii Nauk SSSR (1952), 82 615-17.
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. Harris RC, Tallon MJ, Dunnett M, Boobis L, Coakley J, Kim HJ, Fallowfield JL, Hill CA, Sale C, Wise JA: The absorption of orally supplied beta-alanine and its effect on muscle carnosine synthesis in human vastus lateralis. Amino Acids. 2006 May;30(3):279-89. Epub 2006 Mar 24. Pubmed: 16554972 Link_out
      2. Pagnano MW, Hanssen AD, Lewallen DG, Stuart MJ: Flexion instability after primary posterior cruciate retaining total knee arthroplasty. Clin Orthop Relat Res. 1998 Nov;(356):39-46. Pubmed: 9917666 Link_out
      3. Abe H, Okuma E, Sekine H, Maeda A, Yoshiue S: Human urinary excretion of L-histidine-related compounds after ingestion of several meats and fish muscle. Int J Biochem. 1993 Sep;25(9):1245-9. Pubmed: 8224369 Link_out
      4. Kang I, Han SW: Anserine bursitis in patients with osteoarthritis of the knee. South Med J. 2000 Feb;93(2):207-9. Pubmed: 10701790 Link_out
      5. Magana Loarte JE, Perez Franco J, Sanchez Sanchez G: [Is therapy with local infiltrations feasible in primary care consultations?] Aten Primaria. 1999 Jan;23(1):4-7. Pubmed: 10079554 Link_out
      6. Tan KM, Candlish JK: Carnosine and anserine as modulators of neutrophil function. Clin Lab Haematol. 1998 Aug;20(4):239-44. Pubmed: 9777271 Link_out
      7. Boldyrev A, Abe H: Metabolic transformation of neuropeptide carnosine modifies its biological activity. Cell Mol Neurobiol. 1999 Feb;19(1):163-75. Pubmed: 10079975 Link_out
      8. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Link_out

      Enzymes
      Name: Beta-Ala-His dipeptidase
      Reactions: Not Available
      Gene Name: CNDP1
      Uniprot ID: Q96KN2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Carnosine synthase 1
      Reactions:
      Adenosine triphosphate + 3-Methylhistidine + Beta-Alanine unknown Adenosine monophosphate + Pyrophosphate + Anserine details
      Gene Name: CARNS1
      Uniprot ID: A5YM72 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA