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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:43:57 UTC
HMDB IDHMDB0000194
Secondary Accession Numbers
  • HMDB00194
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.). Anserine is a biomarker for the consumption of meat, especially chicken.
Structure
Data?1563860637
Synonyms
ValueSource
beta-Alanyl-3-methyl-L-histidineChEBI
beta-Alanyl-N(pai)-methyl-L-histidineChEBI
b-Alanyl-3-methyl-L-histidineGenerator
Β-alanyl-3-methyl-L-histidineGenerator
b-Alanyl-N(pai)-methyl-L-histidineGenerator
Β-alanyl-N(pai)-methyl-L-histidineGenerator
L-AnserineHMDB
L-N-b-Alanyl-3-methyl-histidineHMDB
L-N-beta-Alanyl-3-methyl-histidineHMDB
N-b-Alanyl-3-methyl-L-histidineHMDB
N-beta-Alanyl-3-methyl-L-histidineHMDB
BalanineHMDB
Beta Alanyl 3 methylhistidineHMDB
Beta-Alanyl-3-methylhistidineHMDB
OphidineHMDB
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 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
Description belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassHybrid peptides
Direct ParentHybrid peptides
Alternative Parents
Substituents
  • Hybrid peptide
  • Histidine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • N-substituted imidazole
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 Area110.24 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity60.46 m³·mol⁻¹ChemAxon
Polarizability24.3 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-008a-9110000000-2f66d9e2bd58d8fdfe22JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-008a-9220000000-c098b7478e4e2469402cJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0910000000-e359d14a1164b571973eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-0900000000-3ae24b5b69cb5463a956JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0002-7930000000-344e4a7f3b532ce31015JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0090000000-66959f5b2f8cd0fed35dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014r-0950000000-27db9dc4c4fbe3889f7dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-3900000000-e8dd832f2b9453b196fbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9500000000-91673df79b5fb9e1373bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9100000000-468135f3bc158f013255JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-0090000000-5545eb5f0143bc37b54cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-0690000000-65defef60d9fd6e60fe8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-1900000000-1ecb5ca2c9f4935af629JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4j-5900000000-24168da8606d1994f23bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-052b-9400000000-08a9a8a8d83e5958d60eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0920000000-fdb3cabe02ef9f20956dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a4i-0900000000-39c6787170775cf28b30JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a4i-1900000000-a9ee2ab9908f584909b4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0aor-6900000000-934d365646fde55d5c16JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a4i-0900000000-440a3e57f35809ac4568JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-052g-3950000000-656f64d2f4533d03073eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014r-0960000000-1ec10daf4624249b1d5bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xu-1970000000-1e25ebc6c091a98fd2e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3910000000-731cfc3c9901fad1d44bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-3900000000-307d922cb29b8694f151JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1490000000-b93b05b7108f994cf9f6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-5950000000-42d4878fd04fd2f8210eJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Brain
  • Muscle
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified41.0 +/- 10.0 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
UrineDetected and Quantified16.16 umol/mmol creatinineAdult (>18 years old)Male
Normal
    • Shaykhutdinov RA,...
details
UrineDetected and Quantified14.842 +/- 5.257 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
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
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified0.457 +/- 0.214 uMElderly (>65 years old)BothAlzheimer's disease details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    UrineDetected and Quantified12.808 +/- 6.444 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    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 ]
    Colorectal cancer
    1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
    Eosinophilic esophagitis
    1. (). Mordechai, Hien, and David S. Wishart. .
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB021903
    KNApSAcK IDNot Available
    Chemspider ID100482
    KEGG Compound IDC01262
    BioCyc IDCPD-401
    BiGG IDNot Available
    Wikipedia LinkAnserine
    METLIN ID5209
    PubChem Compound112072
    PDB IDNot Available
    ChEBI ID18323
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    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. 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 ]
    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 ]
    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 ]
    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 ]
    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 ]
    6. Tan KM, Candlish JK: Carnosine and anserine as modulators of neutrophil function. Clin Lab Haematol. 1998 Aug;20(4):239-44. [PubMed:9777271 ]
    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 ]
    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. doi: 10.1038/nature07762. [PubMed:19212411 ]

    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