GABAReceptorInhibitorgabareceptorinhibitor

Anserine

By rofalproject
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 ) 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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 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 BalanineMeSH Beta Alanyl 3 methylhistidineMeSH Beta-Alanyl-3-methylhistidineMeSH OphidineMeSH

Chemical Formlia

C10H16N4O3 Average Molecliar Weight

240.259 Monoisotopic Molecliar Weight

240.122240398 IUPAC Name

(2S)-2-(3-aminopropanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid Traditional 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 Description

This compound belongs to the class of chemical entities known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Peptidomimetics Direct Parent

Hybrid peptides Alternative Parents

  • Histidine and derivatives
  • N-acyl-alpha amino acids
  • Imidazolyl carboxylic acids and derivatives
  • N-substituted imidazoles
  • Heteroaromatic compounds
  • Amino acids
  • Monocarboxylic acids and derivatives
  • Propargyl-type 1,3-dipolar organic compounds
  • Carboxylic acids
  • Carboximidic acids
  • Azacyclic compounds
  • Organic oxides
  • Monoalkylamines
  • Organopnictogen compounds
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • 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

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • beta-alanine derivative (CHEBI:18323 )
  • dipeptide (CHEBI:18323 )

    • Ontology Status

    Detected and Quantified Origin

  • Endogenous

    • Biofunction

    Not Available Application

    Not Available Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point226 – 228 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility4.01 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count6ChemAxon Refractivity60.46 m3·mol-1ChemAxon Polarizability24.23 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted GC-MS

    Predicted GC-MS Spectrum – GC-MSNot Available LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0910000000-e359d14a1164b571973eView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-0900000000-3ae24b5b69cb5463a956View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0002-7930000000-344e4a7f3b532ce31015View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0090000000-66959f5b2f8cd0fed35dView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014r-0950000000-27db9dc4c4fbe3889f7dView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-3900000000-e8dd832f2b9453b196fbView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9500000000-91673df79b5fb9e1373bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9100000000-468135f3bc158f013255View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-0090000000-5545eb5f0143bc37b54cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-0690000000-65defef60d9fd6e60fe8View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-1900000000-1ecb5ca2c9f4935af629View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4j-5900000000-24168da8606d1994f23bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-052b-9400000000-08a9a8a8d83e5958d60eView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0920000000-fdb3cabe02ef9f20956dView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a4i-0900000000-39c6787170775cf28b30View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a4i-1900000000-a9ee2ab9908f584909b4View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0aor-6900000000-934d365646fde55d5c16View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a4i-0900000000-440a3e57f35809ac4568View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-052g-3950000000-656f64d2f4533d03073eView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014r-0960000000-1ec10daf4624249b1d5bView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available 1D NMR

    1H NMR SpectrumNot Available 2D NMR

    [1H,13C] 2D NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Saliva
  • Urine

    • Tissue Location

  • Brain
  • Muscle
  • Prostate

    • Pathways

    Name SMPDB Link KEGG Link Beta-Alanine MetabolismSMP00007map00410 Carnosinuria, carnosinemiaSMP00493Not Available GABA-Transaminase DeficiencySMP00351Not Available Ureidopropionase deficiencySMP00492Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified41.0 +/- 10.0 uMAdlit (>18 years old)BothNormal

  • 9267323

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details UrineDetected but not Quantified Adlit (>18 years old)BothNormal

  • 21389975

    • details UrineDetected and Quantified16.16 umol/mmol creatinineAdlit (>18 years old)Male

    Normal

  • Shaykhuspaninov 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 creatinineAdlit (>18 years old)Both

    Normal

  • 24023812

    • details UrineDetected and Quantified<5.921 umol/mmol creatinineAdlit (>18 years old)BothNormal

  • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified0.457 +/- 0.214 uMElderly (>65 years old)BothAlzheimers disease

  • 17031479

    • 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 creatinineAdlit (>18 years old)BothAlzheimers disease

  • 17031479

    • details

    Associated Disorders and Diseases Disease References

    Alzheimers disease

    1. Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimers disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [PubMed:17031479 ]

    Associated OMIM IDs

  • 104300 (Alzheimer's disease)

    • External Links 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 KEGG Compound ID

    C01262 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Anserine NuGOwiki Link

    HMDB00194 Metagene Link

    HMDB00194 METLIN ID

    5209 PubChem Compound

    112072 PDB ID

    Not Available ChEBI ID

    18323

    Product: Urolithin A

    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. 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 ]
    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 + Anserine details

    PMID: 14718577

    By rofalproject

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