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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:20:34 UTC |
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Update Date | 2020-06-04 21:43:45 UTC |
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BMDB ID | BMDB0000177 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | L-Histidine |
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Description | L-Histidine, also known as H, belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives 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. L-Histidine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Histidine exists in all living species, ranging from bacteria to humans. L-Histidine participates in a number of enzymatic reactions, within cattle. In particular, beta-Alanine and L-histidine can be biosynthesized from carnosine; which is catalyzed by the enzyme Beta-ala-his dipeptidase. Furthermore, L-Histidine and beta-alanine can be converted into carnosine through the action of the enzyme carnosine synthase 1. Finally, beta-Alanine and L-histidine can be biosynthesized from carnosine through the action of the enzyme Beta-ala-his dipeptidase. In cattle, L-histidine is involved in a couple of metabolic pathways, which include the histidine metabolism pathway and the beta-alanine metabolism pathway. L-Histidine is a potentially toxic compound. L-Histidine has been found to be associated with several diseases known as autosomal dominant polycystic kidney disease, perillyl alcohol administration for cancer treatment, pyridoxamine 5-prime-phosphate oxidase deficiency, and epilepsy; also l-histidine has been linked to the inborn metabolic disorders including maple syrup urine disease. |
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Structure | |
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Synonyms | Value | Source |
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(S)-4-(2-Amino-2-carboxyethyl)imidazole | ChEBI | (S)-alpha-Amino-1H-imidazole-4-propanoic acid | ChEBI | (S)-alpha-Amino-1H-imidazole-4-propionic acid | ChEBI | H | ChEBI | His | ChEBI | HISTIDINE | ChEBI | L-(-)-Histidine | ChEBI | L-Histidin | ChEBI | (S)-a-Amino-1H-imidazole-4-propanoate | Generator | (S)-a-Amino-1H-imidazole-4-propanoic acid | Generator | (S)-alpha-Amino-1H-imidazole-4-propanoate | Generator | (S)-Α-amino-1H-imidazole-4-propanoate | Generator | (S)-Α-amino-1H-imidazole-4-propanoic acid | Generator | (S)-a-Amino-1H-imidazole-4-propionate | Generator | (S)-a-Amino-1H-imidazole-4-propionic acid | Generator | (S)-alpha-Amino-1H-imidazole-4-propionate | Generator | (S)-Α-amino-1H-imidazole-4-propionate | Generator | (S)-Α-amino-1H-imidazole-4-propionic acid | Generator | (S)-1H-Imidazole-4-alanine | HMDB | (S)-2-Amino-3-(4-imidazolyl)propionsaeure | HMDB | (S)-Histidine | HMDB | (S)1H-Imidazole-4-alanine | HMDB | 3-(1H-Imidazol-4-yl)-L-alanine | HMDB | Amino-1H-imidazole-4-propanoate | HMDB | Amino-1H-imidazole-4-propanoic acid | HMDB | Amino-4-imidazoleproprionate | HMDB | Amino-4-imidazoleproprionic acid | HMDB | Glyoxaline-5-alanine | HMDB | Histidine, L isomer | HMDB | Histidine, L-isomer | HMDB | L-Isomer histidine | HMDB | L-Histidine | KEGG |
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Chemical Formula | C6H9N3O2 |
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Average Molecular Weight | 155.1546 |
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Monoisotopic Molecular Weight | 155.069476547 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 71-00-1 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1 |
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InChI Key | HNDVDQJCIGZPNO-YFKPBYRVSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives 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
- Azole
- Imidazole
- Heteroaromatic compound
- Amino acid
- Carboxylic acid
- Azacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen 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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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | |
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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 | 287 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 45.6 mg/mL | Not Available | LogP | -3.32 | CHMELIK,J ET AL. (1991) |
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Predicted Properties | Not Available |
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Spectra |
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Spectra | |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - All Tissues
- Blood
- Colostrum
- Liver
- Longissimus Thoracis Muscle
- Milk
- Muscle
- Placenta
- Prostate Tissue
- Ruminal Fluid
- Semen
- Semimembranosus Muscle
- Testis
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Pathways | |
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Normal Concentrations |
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All Tissues | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 74-84 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 91.6 uM | Not Specified | Both | Normal | | details | Blood | Detected and Quantified | 76-93 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 52.3-54.5 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 78 +/- 10 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected and Quantified | 382 +/- 67 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Longissimus Thoracis Muscle | Detected and Quantified | 75 +/- 18 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 2.0 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 3.1 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 4.2 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 2.8 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 3 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 2 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 4 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 4 +/- 2 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 134-281 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 58-484 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 43 +/- 9 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 55 +/- 14 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 29 +/- 11 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 32 +/- 10 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 29.7 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 35.2 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 24.8 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 31.8 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 16.1 uM | Not Specified | Both | Normal | | details | Ruminal Fluid | Detected and Quantified | 47.98 +/- 15.77 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 44 +/- 28 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 42.9 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 55.1 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 28.8 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 48 uM | Not Specified | Not Specified | Normal | | details | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Semimembranosus Muscle | Detected and Quantified | 85 +/- 20 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 20 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 61 +/- 13 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Treated with growth-promoting hormones | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | All Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Mycobacterium avium subsp. paratuberculosis infection | | details | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Commercial Product/bacterial growth on ground beef | | details | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Commercial Product/bacterial growth on ground beef | | details | Ruminal Fluid | Detected and Quantified | 28.84 +/- 10.52 uM | Not Specified | Not Specified | Rumen acidosis | | details |
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External Links |
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HMDB ID | HMDB0000177 |
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DrugBank ID | DB00117 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB011856 |
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KNApSAcK ID | C00001363 |
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Chemspider ID | 6038 |
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KEGG Compound ID | C00135 |
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BioCyc ID | HIS |
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BiGG ID | 33985 |
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Wikipedia Link | L-histidine |
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METLIN ID | 21 |
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PubChem Compound | 6274 |
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PDB ID | Not Available |
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ChEBI ID | 15971 |
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References |
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Synthesis Reference | Aurelio Luigi; Brownlee Robert T C; Hughes Andrew B A novel synthesis of N-methyl asparagine, arginine, histidine, and tryptophan. Organic letters (2002), 4(21), 3767-9. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
- Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
- Fooddata+, The Technical University of Denmark (DTU) [Link]
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