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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:03 UTC
HMDB IDHMDB00194
Secondary Accession NumbersNone
Metabolite Identification
Common NameAnserine
DescriptionThis 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 ) 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
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 FormulaC10H16N4O3
Average Molecular Weight240.259
Monoisotopic Molecular Weight240.122240398
IUPAC Name(2S)-2-(3-aminopropanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
Traditional IUPAC Nameanserine
CAS Registry Number584-85-0
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 KeyMYYIAHXIVFADCU-QMMMGPOBSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassPeptidomimetics
Sub ClassHybrid 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 ParentHybrid Peptides
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point226 - 228 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility4.01 g/LALOGPS
logP-3ALOGPS
logP-4.3ChemAxon
logS-1.8ALOGPS
pKa (strongest acidic)3.44ChemAxon
pKa (strongest basic)9.13ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area110.24ChemAxon
rotatable bond count6ChemAxon
refractivity60.46ChemAxon
polarizability24.23ChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Brain
  • Muscle
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Beta-Alanine MetabolismSMP00007map00410
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified41.0 +/- 10.0 uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified16.16 umol/mmol creatinineAdult (>18 years old)Male
Normal
    • Shaykhutdinov RA,...
details
UrineDetected and Quantified7.0 (3.3 -20.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified<5.921 umol/mmol creatinineAdult (>18 years old)BothNormal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified0.457 +/- 0.214 uMElderly (>65 years old)BothAlzheimer's disease details
    UrineDetected and Quantified8.0 +/- 5.0 umol/mmol creatinineAdult (>18 years old)BothAlzheimer's disease details
    Associated Disorders and Diseases
    Disease References
    Alzheimer's disease
    1. 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
    Associated OMIM IDs
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB021903
    KNApSAcK IDNot Available
    Chemspider ID100482
    KEGG Compound IDC01262
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkAnserine
    NuGOwiki LinkHMDB00194
    Metagene LinkHMDB00194
    METLIN ID5209
    PubChem Compound112072
    PDB IDNot Available
    ChEBI ID18323
    References
    Synthesis ReferenceYudaev, N. A. Biosynthesis of anserine. Doklady Akademii Nauk SSSR (1952), 82 615-17.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. 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
    2. 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
    3. 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
    4. 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
    5. Kang I, Han SW: Anserine bursitis in patients with osteoarthritis of the knee. South Med J. 2000 Feb;93(2):207-9. Pubmed: 10701790
    6. 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
    7. Tan KM, Candlish JK: Carnosine and anserine as modulators of neutrophil function. Clin Lab Haematol. 1998 Aug;20(4):239-44. Pubmed: 9777271
    8. Boldyrev A, Abe H: Metabolic transformation of neuropeptide carnosine modifies its biological activity. Cell Mol Neurobiol. 1999 Feb;19(1):163-75. Pubmed: 10079975

    Enzymes

    General function:
    Involved in metallopeptidase activity
    Specific function:
    Preferential hydrolysis of the beta-Ala-|-His dipeptide (carnosine), and also anserine, Xaa-|-His dipeptides and other dipeptides including homocarnosine
    Gene Name:
    CNDP1
    Uniprot ID:
    Q96KN2
    Molecular weight:
    56691.6
    General function:
    Involved in catalytic activity
    Specific function:
    Catalyzes the synthesis of carnosine and homocarnosine. Carnosine is synthesized more efficiently than homocarnosine.
    Gene Name:
    CARNS1
    Uniprot ID:
    A5YM72
    Molecular weight:
    101318.725
    Reactions
    Adenosine triphosphate + 3-Methylhistidine + Beta-Alanine → Adenosine monophosphate + Pyrophosphate + Anserinedetails