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Human Metabolome Database Version 2.5

 

Showing metabocard for Anserine (HMDB00194)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2010-04-12 15:55:44
Accession Number HMDB00194
Secondary Accession Numbers Not Available
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.)
Synonyms
  1. Anserine
  2. L-Anserine
  3. L-N-b-alanyl-3-methyl-Histidine
  4. N-b-alanyl-3-methyl-L-Histidine
  5. N-beta-Alanyl-3-methyl-L-histidine
  6. beta-alanyl-N(pai)-methyl-L-histidine
  7. L-N-beta-alanyl-3-methyl-Histidine
Chemical IUPAC Name 2-(3-aminopropanoylamino)-3-(3-methylimidazol-4-yl)-propanoic acid
Chemical Formula C10H16N4O3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Polypeptides
Sub Class
  • Dipeptides
Family
  • Mammalian Metabolite
Species
  • primary amine
  • primary aliphatic amine (alkylamine)
  • carboxylic acid
  • secondary carboxylic acid amide
  • aromatic compound
  • heterocyclic compound
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 240.259
Monoisotopic Molecular Weight 240.122238
Isomeric SMILES CN1C=NC=C1C[C@H](NC(=O)CCN)C(O)=O
Canonical SMILES CN1C=NC=C1CC(NC(=O)CCN)C(O)=O
KEGG Compound ID C01262 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Anserine Link Image
NuGOwiki Link HMDB00194 Link Image
Metagene Link HMDB00194 Link Image
METLIN ID 5209 Link Image
PubChem Compound 112072 Link Image
PubChem Substance 10629587 Link Image
ChEBI ID 18323 Link Image
CAS Registry Number 584-85-0
InChI Identifier InChI=1/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
Synthesis Reference Yudaev, N. A. Biosynthesis of anserine. Doklady Akademii Nauk SSSR (1952), 82 615-17.
Melting Point (Experimental) 226-228 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 15.8 mg/mL [MEYLAN,WM et al. (1996)]; 4.01 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -2.95 [Predicted by ALOGPS]; -3.8 [Predicted by PubChem via XLOGP]; -1.26 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location
  • Blood
  • Urine
Tissue Location
Tissue References
Brain —
Muscle —
Concentrations (Normal)
Biofluid Blood
Value 41.0 +/- 10.0 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Le Boucher J, Charret C, Coudray-Lucas C, Giboudeau J, Cynober L: Amino acid determination in biological fluids by automated ion-exchange chromatography: performance of Hitachi L-8500A. Clin Chem. 1997 Aug;43(8 Pt 1):1421-8. [PubMed Link Image]
Biofluid Urine
Value <5.921 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Doctor's Data
Biofluid Urine
Value 224 uM
Age Adult:>18 yrs old
Sex Male
Patient information Normal
Comments Based on one experiment
References
  • Shaykhutdinov RA, MacInnis GD, Dowlatabadi R, Weljie AM, Vogel HJ. Quantitative analysis of metabolite concentrations in human urine samples using 13C{1H} NMR spectroscopy. Metabolomics. 2009
Concentrations (Abnormal)
Biofluid Blood
Value 0.457 +/- 0.214 uM
Age Elderly:>65 yrs old
Sex Both
Condition Alzheimer's disease
Comments Not Available
References
  • 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 Link Image]
Biofluid Urine
Value 8.0 +/- 5.0 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Condition Alzheimer's disease
Comments Not Available
References
  • 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 Link Image]
Associated Disorders
Condition References
Alzheimer's disease
  • 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 Link Image]
OMIM ID
Pathways
Name SMPDB Link KEGG Link
Beta-Alanine Metabolism SMP00007 Link Image map00410 Link Image
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 Link Image]
  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 Link Image]
  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 Link Image]
  4. Kang I, Han SW: Anserine bursitis in patients with osteoarthritis of the knee. South Med J. 2000 Feb;93(2):207-9. [PubMed Link Image]
  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 Link Image]
  6. Tan KM, Candlish JK: Carnosine and anserine as modulators of neutrophil function. Clin Lab Haematol. 1998 Aug;20(4):239-44. [PubMed Link Image]
  7. Boldyrev A, Abe H: Metabolic transformation of neuropeptide carnosine modifies its biological activity. Cell Mol Neurobiol. 1999 Feb;19(1):163-75. [PubMed Link Image]
  8. Wikipedia Link Image
Metabolic Enzymes
  1. Beta-Ala-His dipeptidase precursor
Enzyme 1 [top]
Enzyme 1 ID 5713
Enzyme 1 Name Beta-Ala-His dipeptidase precursor
Enzyme 1 Synonyms
  1. Carnosine dipeptidase 1
  2. CNDP dipeptidase 1
  3. Serum carnosinase
  4. Glutamate carboxypeptidase-like protein 2
Enzyme 1 Gene Name CNDP1
Enzyme 1 Protein Sequence >Beta-Ala-His dipeptidase precursor 
MDPKLGRMAASLLAVLLLLLERGMFSSPSPPPALLEKVFQYIDLHQDEFVQTLKEWVAIE
SDSVQPVPRFRQELFRMMAVAADTLQRLGARVASVDMGPQQLPDGQSLPIPPVILAELGS
DPTKGTVCFYGHLDVQPADRGDGWLTDPYVLTEVDGKLYGRGATDNKGPVLAWINAVSAF
RALEQDLPVNIKFIIEGMEEAGSVALEELVEKEKDRFFSGVDYIVISDNLWISQRKPAIT
YGTRGNSYFMVEVKCRDQDFHSGTFGGILHEPMADLVALLGSLVDSSGHILVPGIYDEVV
PLTEEEINTYKAIHLDLEEYRNSSRVEKFLFDTKEEILMHLWRYPSLSIHGIEGAFDEPG
TKTVIPGRVIGKFSIRLVPHMNVSAVEKQVTRHLEDVFSKRNSSNKMVVSMTLGLHPWIA
NIDDTQYLAAKRAIRTVFGTEPDMIRDGSTIPIAKMFQEIVHKSVVLIPLGAVDDGEHSQ
NEKINRWNYIEGTKLFAAFFLEMAQLH
Enzyme 1 Number of Residues 507
Enzyme 1 Molecular Weight 56693
Enzyme 1 Theoretical pI 4.95
Enzyme 1 GO Classification
Function
  • binding
  • catalytic activity
  • hydrolase activity
  • metallopeptidase activity
  • peptidase activity
  • protein binding
  • protein dimerization activity
Process
  • cellular protein metabolism
  • macromolecule metabolism
  • metabolism
  • physiological process
  • protein metabolism
  • proteolysis
Component
—
Enzyme 1 General Function Amino acid transport and metabolism
Enzyme 1 Specific Function Preferential hydrolysis of the beta-Ala-|-His dipeptide (carnosine), and also anserine, Xaa-|-His dipeptides and other dipeptides including homocarnosine
Enzyme 1 Pathways
Enzyme 1 Reactions
  • Preferential hydrolysis of the beta-Ala-|-His dipeptide (carnosine), and also anserine, Xaa-|-His dipeptides and other dipeptides including homocarnosine
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • 1-26
Enzyme 1 Transmembrane Regions Not Available
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 16555792 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q96KN2 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name CNDP1_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1527 bp 
ATGGATCCCAAACTCGGGAGAATGGCTGCGTCCCTGCTGGCTGTGCTGCTGCTGCTGCTG
CTGGAGCGCGGCATGTTCTCCTCACCCTCCCCGCCCCCGGCGCTGTTAGAGAAAGTCTTC
CAGTACATTGACCTCCATCAGGATGAATTTGTGCAGACGCTGAAGGAGTGGGTGGCCATC
GAGAGCGACTCTGTCCAGCCTGTGCCTCGCTTCAGACAAGAGCTCTTCAGAATGATGGCC
GTGGCTGCGGACACGCTGCAGCGCCTGGGGGCCCGTGTGGCCTCGGTGGACATGGGTCCT
CAGCAGCTGCCCGATGGTCAGAGTCTTCCAATACCTCCCGTCATCCTGGCCGAACTGGGG
AGCGATCCCACGAAAGGCACCGTGTGCTTCTACGGCCACTTGGACGTGCAGCCTGCTGAC
CGGGGCGATGGGTGGCTCACGGACCCCTATGTGCTGACGGAGGTAGGCGGGAAACTTTAT
GGACGAGGAGCGACCGACAACAAAGGCCCTGTCTTGGCTTGGATCAATGCTGTGAGCGCC
TTCAGAGCCCTGGAGCAAGATCTTCCTGTGAATATCAAATTCATCATTGAGGGGATGGAA
GAGGCTGGCTCTGTTGCCCTGGAGGAACTTGTGGAAAAAGAAAAGGACCGATTCTTCTCT
GGTGTGGACTACATTGTAATTTCAGATAACCTGTGGATCAGCCAAAGGAAGCTAGCAATC
ACTTACGGAACCCGGGGGAACAGCTACTTCATGGTGGAGGTGAAATGCAGAGACCAGGAT
TTTCACTCAGGAACCTTTGGTGGCATCCTTCATGAACTAATGGCTGATCTGGTTGCTCTT
CTCGGTAGCCTGGTAGACTCGTCTGGTCATATCCTGGTCCCTGGAATCTATGATGAAGTG
GTTCCTCTTACAGAAGAGGAAATAAATACATACAAAGCCATCCATCTAGACCTAGAAGAA
TACCGGAATAGCAGCCGGGTTGAGAAATTTCTGTTCGATACTAAGGAGGAGATTCTAATG
CACCTCTGGAGGTACCCATCTCTTTCTATTCATGGGATCGAGGGCGCGTTTGATGAGCCT
GGAACTAAAACAGTCATACCTGGCCGAGTTATAGGAAAATTTTCAATCCGTCTAGTCCCT
CACATGAATGTGTCTGCGGTGGAAAAACAGGTGACACGACATCTTGAAGATGTGTTCTCC
AAAAGAAATAGTTCCAACAAGATGGTTGTTTCCATGACTCTAGGACTACACCCGTGGATT
GCAAATATTGATGACACTCAGTATCTCGCAGCAAAAAGAGCGATCAGAACAGTGTTTGGA
ACAGAACCAGATATGATCCGGGATGGATCCACCATTCCAATTGCCAAAATGTTCCAGGAG
ATCGTCCACAAGAGCGTGGTGCTAATTCCGCTGGGAGCTGTTGATGATGGAGAACATTCG
CAGAATGAGAAAATCAACAGGTGGAACTACATAGAGGGAACCAAATTATTTGCTGCCTTT
TTCTTAGAGATGGCCCAGCTCCATTAA
Enzyme 1 GenBank Gene ID AJ417564 Link Image
Enzyme 1 GeneCard ID CNDP1 Link Image
Enzyme 1 GenAtlas ID CNDP1 Link Image
Enzyme 1 HGNC ID HGNC:20675 Link Image
Enzyme 1 Chromosome Location 18
Enzyme 1 Locus 18q22.3
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Clark HF, Gurney AL, Abaya E, Baker K, Baldwin D, Brush J, Chen J, Chow B, Chui C, Crowley C, Currell B, Deuel B, Dowd P, Eaton D, Foster J, Grimaldi C, Gu Q, Hass PE, Heldens S, Huang A, Kim HS, Klimowski L, Jin Y, Johnson S, Lee J, Lewis L, Liao D, Mark M, Robbie E, Sanchez C, Schoenfeld J, Seshagiri S, Simmons L, Singh J, Smith V, Stinson J, Vagts A, Vandlen R, Watanabe C, Wieand D, Woods K, Xie MH, Yansura D, Yi S, Yu G, Yuan J, Zhang M, Zhang Z, Goddard A, Wood WI, Godowski P, Gray A: The secreted protein discovery initiative (SPDI), a large-scale effort to identify novel human secreted and transmembrane proteins: a bioinformatics assessment. Genome Res. 2003 Oct;13(10):2265-70. Epub 2003 Sep 15. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available