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Human Metabolome Database Version 3.5

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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 | 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 Comments
Blood Detected and Quantified
Article_icon
41.0 +/- 10.0 uM Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
16.16 umol/mmol creatinine Adult (>18 years old) Male Normal Based on one experiment
Urine Detected and Quantified
Article_icon
7.0 (3.3 -20.0) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and Quantified
<5.921 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.457 +/- 0.214 uM Elderly (>65 years old) Both Alzheimer's disease Not Available
Urine Detected and Quantified
Article_icon
8.0 +/- 5.0 umol/mmol creatinine Adult (>18 years old) Both Alzheimer's disease Not Available
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
    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:
    • Preferential hydrolysis of the beta-Ala!His dipeptide (carnosine), and also anserine, Xaa!His dipeptides and other dipeptides including homocarnosine [RN:R01166 R03288] ALL_REAC R01166 R03288 COFACTOR Citrate [CPD:C00158]
    • Cadmium [CPD:C01413]
    Gene Name: CNDP1
    Uniprot ID: Q96KN2 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA