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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2018-04-16 17:00:02 UTC |
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HMDB ID | HMDB0000001 |
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Secondary Accession Numbers | - HMDB00001
- HMDB0004935
- HMDB0006703
- HMDB0006704
- HMDB04935
- HMDB06703
- HMDB06704
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Metabolite Identification |
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Common Name | 1-Methylhistidine |
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Description | One-methylhistidine (1-MHis) is derived mainly from the anserine of dietary flesh sources, especially poultry. The enzyme, carnosinase, splits anserine into b-alanine and 1-MHis. High levels of 1-MHis tend to inhibit the enzyme carnosinase and increase anserine levels. Conversely, genetic variants with deficient carnosinase activity in plasma show increased 1-MHis excretions when they consume a high meat diet. Reduced serum carnosinase activity is also found in patients with Parkinson's disease and multiple sclerosis and patients following a cerebrovascular accident. Vitamin E deficiency can lead to 1-methylhistidinuria from increased oxidative effects in skeletal muscle. 1-Methylhistidine is a biomarker for the consumption of meat, especially red meat. |
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Structure | |
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Synonyms | Value | Source |
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(2S)-2-amino-3-(1-Methyl-1H-imidazol-4-yl)propanoic acid | ChEBI | 1-Methylhistidine | ChEBI | Pi-methylhistidine | ChEBI | (2S)-2-amino-3-(1-Methyl-1H-imidazol-4-yl)propanoate | Generator | 1 Methylhistidine | HMDB | 1-Methyl histidine | HMDB | 1-Methyl-histidine | HMDB | 1-Methyl-L-histidine | HMDB | 1-MHis | HMDB | 1-N-Methyl-L-histidine | HMDB | L-1-Methylhistidine | HMDB | N1-Methyl-L-histidine | HMDB | 1-Methylhistidine dihydrochloride | MeSH |
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Chemical Formula | C7H11N3O2 |
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Average Molecular Weight | 169.1811 |
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Monoisotopic Molecular Weight | 169.085126611 |
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IUPAC Name | (2S)-2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid |
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Traditional Name | 1 methylhistidine |
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CAS Registry Number | 332-80-9 |
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SMILES | CN1C=NC(C[C@H](N)C(O)=O)=C1 |
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InChI Identifier | InChI=1S/C7H11N3O2/c1-10-3-5(9-4-10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1 |
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InChI Key | BRMWTNUJHUMWMS-LURJTMIESA-N |
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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as histidine and derivatives. These are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Histidine and derivatives |
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Alternative Parents | |
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Substituents | - Histidine or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Imidazolyl carboxylic acid derivative
- Aralkylamine
- N-substituted imidazole
- Azole
- Imidazole
- Heteroaromatic compound
- Amino acid
- Carboxylic acid
- Azacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Primary amine
- Primary aliphatic amine
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Amine
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 249 | http://download.cappchem.com/data/Properties-of-Amino-Acids.pdf | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0002-9610000000-d0147d3e28362f91174a | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-0gbd-4941000000-cee19577c72eecd95aec | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0002-9610000000-d0147d3e28362f91174a | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0gbd-4941000000-cee19577c72eecd95aec | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00dm-9500000000-e50450f2dc8a5d4b3655 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9310000000-d6f7eb07e6f5ecb74263 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00di-0900000000-037d24a7d65676b7e356 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-0900000000-03e99316bd6c098f5d11 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00ea-9800000000-a33c82a1c91f56d372fe | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-695bcc2d0a01df2d7521 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-0900000000-4eea9cf6f12f18d06f98 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05us-9300000000-072d6fe7a7a03cd7390b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-1900000000-57f1e30ae8b606ea5f5c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01b9-5900000000-ff71b6d300a9ee595b3c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0adj-9300000000-e045823003ab541d5b1e | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Urine
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Tissue Location | |
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Pathways | Name | SMPDB/Pathwhiz | KEGG | Histidine Metabolism |    |  | Histidinemia |    | Not Available |
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Normal Concentrations |
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Blood | Detected and Quantified | 7.7 +/- 1.9 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 14.4 +/- 2.3 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 19.6 +/- 2.6 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 12.7 +/- 2.9 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 20.2 +/- 4.0 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 9.1 +/- 7.2 uM | Children (1-13 years old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 4.0 +/- 8.0 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 4.0 +/- 1.74 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Not Specified | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 26.34 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 10-17 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected but not Quantified | | Not Available | Male | Normal | | details | Urine | Detected and Quantified | 17.74-153.77 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 8.3 (2.4-28.4) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 15.9 +/- 19.5 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 46.0833 +/- 53.432 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 11-16 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 45.473 +/- 41.617 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 15.919 +/- 19.503 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 4.635 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 33.624 +/- 36.360 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 28.0954 +/- 31.826 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 2.340 +/- 5.0764 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 1.334 +/- 2.759 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 30.0 +/- 43.0 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 4.6 +/- 2.7 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 2.3 +/- 5.1 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 46.1 +/- 53.5 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 15.9 +/- 19.5 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 28.1 +/- 31.8 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 1.3 +/- 2.76 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 45.5 +/- 41.6 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 33.6 +/- 36.4 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 21.329 +/- 12.971 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 51.2 +/- 17.6 uM | Adult (>18 years old) | Female | Pregnancy with fetuses with trisomy 18 | | details | Blood | Detected and Quantified | 43.4 +/- 22.3 uM | Adult (>18 years old) | Female | Pregnancy | | details | Blood | Detected and Quantified | 50.7 (12.9) uM | Adult (>18 years old) | Female | Early preeclampsia | | details | Blood | Detected and Quantified | 50.0 (14.6) uM | Adult (>18 years old) | Female | Pregnancy | | details | Blood | Detected and Quantified | 28.8 +/- 18.2 uM | Adult (>18 years old) | Both | Kidney disease | | details | Blood | Detected and Quantified | 83.1 +/- 21.7 uM | Adult (>18 years old) | Both | Kidney disease | | details | Blood | Detected and Quantified | 70.3 (40.0) uM | Adult (>18 years old) | Female | Late-onset preeclampsia | | details | Blood | Detected and Quantified | 38.9 (20.3) uM | Adult (>18 years old) | Female | Pregnancy | | details | Blood | Detected and Quantified | 10.66 +/- 2.68 uM | Elderly (>65 years old) | Both | Alzheimer's disease | | details | Blood | Detected and Quantified | 40.4 (12.3) uM | Adult (>18 years old) | Female | Down syndrome pregnancy | | details | Blood | Detected and Quantified | 32.7 (13.7) uM | Adult (>18 years old) | Female | Pregnancy | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 2.6 +/- 1.13 uM | Adult (>18 years old) | Both | Alzheimer's disease | | details | Urine | Detected and Quantified | 10.9 +/- 10.1 umol/mmol creatinine | Adult (>18 years old) | Both | Obesity | | details | Urine | Detected and Quantified | 17.5 +/- 25.7 umol/mmol creatinine | Adult (>18 years old) | Both | Diabetes | | details | Urine | Detected and Quantified | 15.7 +/- 4.04 umol/mmol creatinine | Adult (>18 years old) | Both | Alzheimer's disease | | details | Urine | Detected and Quantified | 18.299 +/- 16.521 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 40 +/- 2.6 umol/mmol creatinine | Adult (>18 years old) | Both | Propionic acidemia | | details | Urine | Detected and Quantified | 31 +/- 11 umol/mmol creatinine | Adult (>18 years old) | Both | Maple syrup urine disease | | details | Urine | Detected and Quantified | 50.3 +/- 9.9 umol/mmol creatinine | Adult (>18 years old) | Both | Aminoaciduria | | details |
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Associated Disorders and Diseases |
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Disease References | Alzheimer's disease |
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- 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 ]
| Diabetes mellitus type 2 |
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- Tuma P, Samcova E, Balinova P: Determination of 3-methylhistidine and 1-methylhistidine in untreated urine samples by capillary electrophoresis. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jul 5;821(1):53-9. [PubMed:15899597 ]
| Kidney disease |
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- Raj DS, Ouwendyk M, Francoeur R, Pierratos A: Plasma amino acid profile on nocturnal hemodialysis. Blood Purif. 2000;18(2):97-102. [PubMed:10838467 ]
| Obesity |
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- Tuma P, Samcova E, Balinova P: Determination of 3-methylhistidine and 1-methylhistidine in untreated urine samples by capillary electrophoresis. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jul 5;821(1):53-9. [PubMed:15899597 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | DB04151 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB012119 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 83153 |
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KEGG Compound ID | C01152 |
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BioCyc ID | CPD-1823 |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | 3741 |
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PubChem Compound | 92105 |
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PDB ID | HIC |
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ChEBI ID | 50599 |
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References |
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Synthesis Reference | Jain, Rahul; Cohen, Louis A. Regiospecific alkylation of histidine and histamine at N-1 (t).Tetrahedron (1996), 52(15), 5363-70. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Colombani PC, Kovacs E, Frey-Rindova P, Frey W, Langhans W, Arnold M, Wenk C: Metabolic effects of a protein-supplemented carbohydrate drink in marathon runners. Int J Sport Nutr. 1999 Jun;9(2):181-201. [PubMed:10362454 ]
- Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. [PubMed:7762816 ]
- Myint T, Fraser GE, Lindsted KD, Knutsen SF, Hubbard RW, Bennett HW: Urinary 1-methylhistidine is a marker of meat consumption in Black and in White California Seventh-day Adventists. Am J Epidemiol. 2000 Oct 15;152(8):752-5. [PubMed:11052553 ]
- Giesecke K, Magnusson I, Ahlberg M, Hagenfeldt L, Wahren J: Protein and amino acid metabolism during early starvation as reflected by excretion of urea and methylhistidines. Metabolism. 1989 Dec;38(12):1196-200. [PubMed:2593832 ]
- Vranic L, Granic P, Rajic Z: Basic amino acid in the pathogenesis of caries. Acta Stomatol Croat. 1991;25(2):71-6. [PubMed:1819935 ]
- Sjolin J, Stjernstrom H, Henneberg S, Hambraeus L, Friman G: Evaluation of urinary 3-methylhistidine excretion in infection by measurements of 1-methylhistidine and the creatinine ratios. Am J Clin Nutr. 1989 Jan;49(1):62-70. [PubMed:2912013 ]
- COCKS DH, DENNIS PO, NELSON TH: ISOLATION OF 3-METHYL HISTIDINE FROM WHALEMEAT EXTRACT AND THE PREPARATION OF SOME DERIVATIVES. Nature. 1964 Apr 11;202:184-5. [PubMed:14156296 ]
- Dohm GL, Williams RT, Kasperek GJ, van Rij AM: Increased excretion of urea and N tau -methylhistidine by rats and humans after a bout of exercise. J Appl Physiol Respir Environ Exerc Physiol. 1982 Jan;52(1):27-33. [PubMed:7061274 ]
- Garlick PJ, McNurlan MA, Bark T, Lang CH, Gelato MC: Hormonal regulation of protein metabolism in relation to nutrition and disease. J Nutr. 1998 Feb;128(2 Suppl):356S-359S. [PubMed:9478024 ]
- Tuma P, Samcova E, Balinova P: Determination of 3-methylhistidine and 1-methylhistidine in untreated urine samples by capillary electrophoresis. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jul 5;821(1):53-9. [PubMed:15899597 ]
- Dunnett M, Harris RC: High-performance liquid chromatographic determination of imidazole dipeptides, histidine, 1-methylhistidine and 3-methylhistidine in equine and camel muscle and individual muscle fibres. J Chromatogr B Biomed Sci Appl. 1997 Jan 10;688(1):47-55. [PubMed:9029312 ]
- Betto P, Ricciarello G, Pichini S, Dello Strologo L, Rizzoni G: High-performance liquid chromatography-electrochemical detection of 3-methylhistidine in human urine. J Chromatogr. 1992 Dec 23;584(2):256-60. [PubMed:1484110 ]
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