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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:59:07 UTC
NP-MRD IDNP0001411
Secondary Accession NumbersNone
Natural Product Identification
Common NameAnserine
DescriptionAnserine (beta-alanyl-N-3-methylhistidine) is a dipeptide containing beta-alanine and 3-methylhistidine. It is a derivative of carnosine, which had been methylated. The methyl group of anserine is added to carnosine by the enzyme S-adenosylmethionine: Carnosine N-methyltransferase (PMID: 29484990 ). The enzyme is closely related to histamine N-methyltransferase and appears to be present in a majority of anserine-producing species (PMID: 23705015 ). Anserine is a generally a more metabolically stable derivative of carnosine. Anserine can be found in the skeletal muscle and brain of certain mammals (rabbits, cattle), migratory fish and birds. This dipeptide is normally absent from human tissues and body fluids, and its appearance there is usually an artifact of diet. Anserine can also arise from serum carnosinase deficiency. (OMIM 212200 ). Anserine was first discovered in goose muscle in 1929, and was named after this extraction (anser is Latin for goose). Anserine, which is water-soluble, is found at high levels in the muscles of different non-human vertebrates, with poultry, rabbit, tuna, plaice, and salmon having generally higher contents than other marine foods, beef, or pork (PMID: 31908682 ). An increase of urinary anserine excretion has been found in humans after the consumption of chicken, rabbit, and tuna and has been associated with intake of chicken, salmon, and, to a lesser extent, beef (PMID: 31908682 ). Anserine can undergo cleavage to give rise to 3-methylhistidine.(3-MH). The dipeptide balenine, common in some whales, cleaves to form 1-methylhistidine (1-MH) (PMID: 31908682 ). There is considerable confusion with regard to the nomenclature of the methylated nitrogen atoms on the imidazole ring of histidine and other histidine-containing peptides such as anserine. In particular, older literature (mostly prior to the year 2000) designated anserine (N-pi methylated) as beta-alanyl-N1-methyl-histidine, whereas according to standard IUPAC nomenclature, anserine is correctly named as beta-alanyl-N3-methyl-histidine. As a result, many papers published prior to the year 2000 incorrectly identified 1MH as a specific marker for dietary consumption of certain foods or various pathophysiological effects when they really were referring to 3MH or vice versa (PMID: 24137022 ). In particular balenine (a whale or snake-specific dipeptide with 1MH) was often confused with anserine (the poultry dipeptide with 3MH). An animal model study of Alzheimer's disease using mice found that treatment with anserine reduced memory loss (PMID: 28974740 ). Anserine reduced glial inflammatory activity (particularly of astrocyte). The study also found that anserine-treated mice had greater pericyte surface area. The greater area of pericytes was commensurate with improved memory. The anserine-treated mice overall performed better on a spatial memory test (Morris Water Maze) (PMID: 28974740 ). A human study on 84 elderly subjects showed that subjects who took anserine and carnosine supplements for one year showed increased blood flow in the prefrontal cortex on MRI (PMID: 29896423 ).
Structure
Thumb
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 Mass240.2590 Da
Monoisotopic Mass240.12224 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
  • Animalia
  • Species Where Detected
    Species NameSourceReference
    Homo sapiens (Urine)KNApSAcK Database
    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
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting Point226 - 228 °CNot Available
    Boiling Point611.30 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
    Water Solubility15750 mg/L @ 25 °C (est)The Good Scents Company Information System
    LogP-2.220 (est)The Good Scents Company Information System
    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
    BioavailabilityYesChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterNoChemAxon
    Veber's RuleNoChemAxon
    MDDR-like RuleNoChemAxon
    HMDB IDHMDB0000194
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB021903
    KNApSAcK IDC00052191
    Chemspider ID100482
    KEGG Compound IDC01262
    BioCyc IDCPD-401
    BiGG IDNot Available
    Wikipedia LinkAnserine
    METLIN ID5209
    PubChem Compound112072
    PDB IDNot Available
    ChEBI ID18323
    Good Scents IDrw1692971
    References
    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 ]
    9. Boldyrev AA, Aldini G, Derave W: Physiology and pathophysiology of carnosine. Physiol Rev. 2013 Oct;93(4):1803-45. doi: 10.1152/physrev.00039.2012. [PubMed:24137022 ]
    10. Kwiatkowski S, Kiersztan A, Drozak J: Biosynthesis of Carnosine and Related Dipeptides in Vertebrates. Curr Protein Pept Sci. 2018;19(8):771-789. doi: 10.2174/1389203719666180226155657. [PubMed:29484990 ]
    11. Drozak J, Chrobok L, Poleszak O, Jagielski AK, Derlacz R: Molecular identification of carnosine N-methyltransferase as chicken histamine N-methyltransferase-like protein (hnmt-like). PLoS One. 2013 May 21;8(5):e64805. doi: 10.1371/journal.pone.0064805. Print 2013. [PubMed:23705015 ]
    12. Cuparencu C, Pratico G, Hemeryck LY, Sri Harsha PSC, Noerman S, Rombouts C, Xi M, Vanhaecke L, Hanhineva K, Brennan L, Dragsted LO: Biomarkers of meat and seafood intake: an extensive literature review. Genes Nutr. 2019 Dec 30;14:35. doi: 10.1186/s12263-019-0656-4. eCollection 2019. [PubMed:31908682 ]
    13. Kaneko J, Enya A, Enomoto K, Ding Q, Hisatsune T: Anserine (beta-alanyl-3-methyl-L-histidine) improves neurovascular-unit dysfunction and spatial memory in aged AbetaPPswe/PSEN1dE9 Alzheimer's-model mice. Sci Rep. 2017 Oct 3;7(1):12571. doi: 10.1038/s41598-017-12785-7. [PubMed:28974740 ]
    14. Ding Q, Tanigawa K, Kaneko J, Totsuka M, Katakura Y, Imabayashi E, Matsuda H, Hisatsune T: Anserine/Carnosine Supplementation Preserves Blood Flow in the Prefrontal Brain of Elderly People Carrying APOE e4. Aging Dis. 2018 Jun 1;9(3):334-345. doi: 10.14336/AD.2017.0809. eCollection 2018 Jun. [PubMed:29896423 ]