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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:27:42 UTC
HMDB IDHMDB0000194
Secondary Accession Numbers
  • HMDB00194
Metabolite 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
Data?1582752115
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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular 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
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available155.2http://allccs.zhulab.cn/database/detail?ID=AllCCS00000009
[M+H]+Not Available154.6http://allccs.zhulab.cn/database/detail?ID=AllCCS00000009
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.5731661259
DarkChem[M-H]-154.29531661259
AllCCS[M+H]+155.09632859911
AllCCS[M-H]-154.54832859911
DeepCCS[M+H]+150.66130932474
DeepCCS[M-H]-148.30330932474
DeepCCS[M-2H]-182.03230932474
DeepCCS[M+Na]+156.88330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AnserineCN1C=NC=C1C[C@H](NC(=O)CCN)C(O)=O3285.6Standard polar33892256
AnserineCN1C=NC=C1C[C@H](NC(=O)CCN)C(O)=O2333.8Standard non polar33892256
AnserineCN1C=NC=C1C[C@H](NC(=O)CCN)C(O)=O2408.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Anserine,1TMS,isomer #1CN1C=NC=C1C[C@H](NC(=O)CCN)C(=O)O[Si](C)(C)C2402.9Semi standard non polar33892256
Anserine,1TMS,isomer #2CN1C=NC=C1C[C@H](NC(=O)CCN[Si](C)(C)C)C(=O)O2498.8Semi standard non polar33892256
Anserine,1TMS,isomer #3CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN)[Si](C)(C)C2320.9Semi standard non polar33892256
Anserine,2TMS,isomer #1CN1C=NC=C1C[C@H](NC(=O)CCN[Si](C)(C)C)C(=O)O[Si](C)(C)C2514.8Semi standard non polar33892256
Anserine,2TMS,isomer #1CN1C=NC=C1C[C@H](NC(=O)CCN[Si](C)(C)C)C(=O)O[Si](C)(C)C2352.8Standard non polar33892256
Anserine,2TMS,isomer #1CN1C=NC=C1C[C@H](NC(=O)CCN[Si](C)(C)C)C(=O)O[Si](C)(C)C3248.9Standard polar33892256
Anserine,2TMS,isomer #2CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN)[Si](C)(C)C2326.9Semi standard non polar33892256
Anserine,2TMS,isomer #2CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN)[Si](C)(C)C2276.0Standard non polar33892256
Anserine,2TMS,isomer #2CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN)[Si](C)(C)C3439.2Standard polar33892256
Anserine,2TMS,isomer #3CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN[Si](C)(C)C)[Si](C)(C)C2403.0Semi standard non polar33892256
Anserine,2TMS,isomer #3CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN[Si](C)(C)C)[Si](C)(C)C2415.1Standard non polar33892256
Anserine,2TMS,isomer #3CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN[Si](C)(C)C)[Si](C)(C)C3309.7Standard polar33892256
Anserine,2TMS,isomer #4CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O2626.2Semi standard non polar33892256
Anserine,2TMS,isomer #4CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O2523.0Standard non polar33892256
Anserine,2TMS,isomer #4CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O3481.3Standard polar33892256
Anserine,3TMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN[Si](C)(C)C)[Si](C)(C)C2413.9Semi standard non polar33892256
Anserine,3TMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN[Si](C)(C)C)[Si](C)(C)C2405.7Standard non polar33892256
Anserine,3TMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN[Si](C)(C)C)[Si](C)(C)C2927.8Standard polar33892256
Anserine,3TMS,isomer #2CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2622.7Semi standard non polar33892256
Anserine,3TMS,isomer #2CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2471.8Standard non polar33892256
Anserine,3TMS,isomer #2CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C3053.3Standard polar33892256
Anserine,3TMS,isomer #3CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2558.7Semi standard non polar33892256
Anserine,3TMS,isomer #3CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2563.4Standard non polar33892256
Anserine,3TMS,isomer #3CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C3114.6Standard polar33892256
Anserine,4TMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2582.3Semi standard non polar33892256
Anserine,4TMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2540.2Standard non polar33892256
Anserine,4TMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2792.4Standard polar33892256
Anserine,1TBDMS,isomer #1CN1C=NC=C1C[C@H](NC(=O)CCN)C(=O)O[Si](C)(C)C(C)(C)C2676.5Semi standard non polar33892256
Anserine,1TBDMS,isomer #2CN1C=NC=C1C[C@H](NC(=O)CCN[Si](C)(C)C(C)(C)C)C(=O)O2732.7Semi standard non polar33892256
Anserine,1TBDMS,isomer #3CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN)[Si](C)(C)C(C)(C)C2598.1Semi standard non polar33892256
Anserine,2TBDMS,isomer #1CN1C=NC=C1C[C@H](NC(=O)CCN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2949.3Semi standard non polar33892256
Anserine,2TBDMS,isomer #1CN1C=NC=C1C[C@H](NC(=O)CCN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2750.8Standard non polar33892256
Anserine,2TBDMS,isomer #1CN1C=NC=C1C[C@H](NC(=O)CCN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3277.2Standard polar33892256
Anserine,2TBDMS,isomer #2CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN)[Si](C)(C)C(C)(C)C2812.6Semi standard non polar33892256
Anserine,2TBDMS,isomer #2CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN)[Si](C)(C)C(C)(C)C2704.1Standard non polar33892256
Anserine,2TBDMS,isomer #2CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN)[Si](C)(C)C(C)(C)C3410.3Standard polar33892256
Anserine,2TBDMS,isomer #3CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2915.2Semi standard non polar33892256
Anserine,2TBDMS,isomer #3CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2794.2Standard non polar33892256
Anserine,2TBDMS,isomer #3CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3309.7Standard polar33892256
Anserine,2TBDMS,isomer #4CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O3066.3Semi standard non polar33892256
Anserine,2TBDMS,isomer #4CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2882.3Standard non polar33892256
Anserine,2TBDMS,isomer #4CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O3461.2Standard polar33892256
Anserine,3TBDMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3090.0Semi standard non polar33892256
Anserine,3TBDMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2969.7Standard non polar33892256
Anserine,3TBDMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3131.5Standard polar33892256
Anserine,3TBDMS,isomer #2CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3292.1Semi standard non polar33892256
Anserine,3TBDMS,isomer #2CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3057.7Standard non polar33892256
Anserine,3TBDMS,isomer #2CN1C=NC=C1C[C@H](NC(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3202.5Standard polar33892256
Anserine,3TBDMS,isomer #3CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3240.2Semi standard non polar33892256
Anserine,3TBDMS,isomer #3CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3100.4Standard non polar33892256
Anserine,3TBDMS,isomer #3CN1C=NC=C1C[C@@H](C(=O)O)N(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3244.9Standard polar33892256
Anserine,4TBDMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3421.1Semi standard non polar33892256
Anserine,4TBDMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3240.6Standard non polar33892256
Anserine,4TBDMS,isomer #1CN1C=NC=C1C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3106.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Anserine GC-MS (Non-derivatized) - 70eV, Positivesplash10-008a-9110000000-2f66d9e2bd58d8fdfe222016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anserine GC-MS (1 TMS) - 70eV, Positivesplash10-008a-9220000000-c098b7478e4e2469402c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anserine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anserine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anserine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anserine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anserine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anserine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0a4i-0910000000-e359d14a1164b571973e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4i-0900000000-3ae24b5b69cb5463a9562012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0002-7930000000-344e4a7f3b532ce310152012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-000i-0090000000-66959f5b2f8cd0fed35d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-014r-0950000000-27db9dc4c4fbe3889f7d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-014i-3900000000-e8dd832f2b9453b196fb2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0a4i-9500000000-91673df79b5fb9e1373b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-0a4i-9100000000-468135f3bc158f0132552012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0006-0090000000-5545eb5f0143bc37b54c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-0006-0690000000-65defef60d9fd6e60fe82012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0a4i-1900000000-1ecb5ca2c9f4935af6292012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-0a4j-5900000000-24168da8606d1994f23b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-052b-9400000000-08a9a8a8d83e5958d60e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-00di-0920000000-fdb3cabe02ef9f20956d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0a4i-0900000000-39c6787170775cf28b302012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0a4i-1900000000-a9ee2ab9908f584909b42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0aor-6900000000-934d365646fde55d5c162012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0a4i-0900000000-440a3e57f35809ac45682012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-052g-3950000000-656f64d2f4533d03073e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Anserine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-014r-0960000000-1ec10daf4624249b1d5b2012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anserine 10V, Positive-QTOFsplash10-00xu-1970000000-1e25ebc6c091a98fd2e92016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anserine 20V, Positive-QTOFsplash10-00di-3910000000-731cfc3c9901fad1d44b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anserine 40V, Positive-QTOFsplash10-00di-3900000000-307d922cb29b8694f1512016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anserine 10V, Negative-QTOFsplash10-000i-1490000000-b93b05b7108f994cf9f62016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anserine 20V, Negative-QTOFsplash10-0079-5950000000-42d4878fd04fd2f8210e2016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Brain
  • Placenta
  • Prostate
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified41.0 +/- 10.0 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified<15.95 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified<41.74 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal details
UrineDetected and Quantified<4.30 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified16.16 umol/mmol creatinineAdult (>18 years old)Male
Normal
    • Shaykhutdinov RA,...
details
UrineDetected and Quantified<31.33 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified14.842 +/- 5.257 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified7.0 (3.3 -20.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified<92.76 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified<45.021 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified<5.921 umol/mmol creatinineAdult (>18 years old)BothNormal
      Not Available
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.457 +/- 0.214 uMElderly (>65 years old)BothAlzheimer's disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified12.808 +/- 6.444 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
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. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000094
Good Scents IDrw1692971
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. 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. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  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 ]

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