1.0 2020-03-18 23:23:15 UTC 2022-12-13 23:36:24 UTC CDB000059 Histidine Histidine, or l-histidine, abbreviated His or H, an alpha-amino acid, is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3. Histidine is an essential amino acid that is not synthesized de novo in humans and must be obtained though ingestion of histidine. L-Histidine is a strong basic compound. It is an odorless white crystalline powder with a bitter taste. In humans, L-histidine is involved in methylhistidine metabolism. Histidine biosynthesis has been well studied in E. coli and involves eight gene products (His1, 2, 3, 4, 5, 6, 7, and 8, from a single gene) and occurs in ten steps. This is possible because a single gene product can catalyze more than one reaction (PMID:8852895). L-Histidine is found in high concentrations in beluga whales, caseins, and bearded seals and in lower concentration in prairie turnips, puddings, and black walnuts. L-Histidine has also been detected in climbing beans, sago palms, vanilla, pitanga (cherry) and allspices making histidine a potential biomarker for the consumption of these foods. Histidine is an amino acid found in cannabis plants (PMID: 6991645). It is a favouring ingredient and dietary supplement. Histidine was shown to have anti-hypertensive effects, decreasing blood pressure, by modulating the histamine H3 receptor (PMID: 19566844). Histidine is a precursor of histamine, an inflammatory product associated with allergies ( https://doi.org/10.1016/B978-0-12-801238-3.66093-2). Histidine can be post-translationally modified to¬†3-methylhistidine, which is excreted in urine and is a¬†biomarker¬†of skeletal muscle damage (PMID: 16079625). (S)-4-(2-Amino-2-carboxyethyl)imidazole (S)-alpha-Amino-1H-imidazole-4-propanoic acid (S)-alpha-Amino-1H-imidazole-4-propionic acid H His HISTIDINE L-(-)-Histidine L-Histidin (S)-a-Amino-1H-imidazole-4-propanoate (S)-a-Amino-1H-imidazole-4-propanoic acid (S)-alpha-Amino-1H-imidazole-4-propanoate (S)-Α-amino-1H-imidazole-4-propanoate (S)-Α-amino-1H-imidazole-4-propanoic acid (S)-a-Amino-1H-imidazole-4-propionate (S)-a-Amino-1H-imidazole-4-propionic acid (S)-alpha-Amino-1H-imidazole-4-propionate (S)-Α-amino-1H-imidazole-4-propionate (S)-Α-amino-1H-imidazole-4-propionic acid (S)-1H-Imidazole-4-alanine (S)-2-Amino-3-(4-imidazolyl)propionsaeure (S)-Histidine (S)1H-Imidazole-4-alanine 3-(1H-Imidazol-4-yl)-L-alanine Amino-1H-imidazole-4-propanoate Amino-1H-imidazole-4-propanoic acid Amino-4-imidazoleproprionate Amino-4-imidazoleproprionic acid Glyoxaline-5-alanine Histidine, L isomer Histidine, L-isomer L-Isomer histidine L-Histidine C6H9N3O2 155.15 155.0695 (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid L-histidine 30641-68-0 N[C@@H](CC1=CN=CN1)C(O)=O 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 HNDVDQJCIGZPNO-YFKPBYRVSA-N 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. Histidine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aromatic heteromonocyclic compounds Amino acids Aralkylamines Azacyclic compounds Carbonyl compounds Carboxylic acids Heteroaromatic compounds Hydrocarbon derivatives Imidazolyl carboxylic acids and derivatives L-alpha-amino acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Alpha-amino acid Amine Amino acid Aralkylamine Aromatic heteromonocyclic compound Azacycle Azole Carbonyl group Carboxylic acid Heteroaromatic compound Histidine or derivatives Hydrocarbon derivative Imidazole Imidazolyl carboxylic acid derivative L-alpha-amino acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Common amino acids L-alpha-amino acid histidine proteinogenic amino acid water_solubility 45.6 mg/mL logp -3.32 CHMELIK,J ET AL. (1991) melting_point 287 °C logp -2.67 ALOGPS logs -0.34 ALOGPS logp -3.6 ChemAxon pka_strongest_acidic 1.85 ChemAxon pka_strongest_basic 9.44 ChemAxon iupac (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid ChemAxon average_mass 155.15 ChemAxon mono_mass 155.0695 ChemAxon smiles N[C@@H](CC1=CN=CN1)C(O)=O ChemAxon formula C6H9N3O2 ChemAxon inchi 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 ChemAxon inchikey HNDVDQJCIGZPNO-YFKPBYRVSA-N ChemAxon polar_surface_area 92 ChemAxon refractivity 38.06 ChemAxon polarizability 14.67 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00135 DB00117 FDB011856 6038 6274 15971 HIS C00001363 33985 L-histidine 21 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Alifano P, Fani R, Lio P, Lazcano A, Bazzicalupo M, Carlomagno MS, Bruni CB: Histidine biosynthetic pathway and genes: structure, regulation, and evolution. Microbiol Rev. 1996 Mar;60(1):44-69. 8852895 Toba H, Nakamori A, Tanaka Y, Yukiya R, Tatsuoka K, Narutaki M, Tokitaka M, Hariu H, Kobara M, Nakata T: Oral L-histidine exerts antihypertensive effects via central histamine H3 receptors and decreases nitric oxide content in the rostral ventrolateral medulla in spontaneously hypertensive rats. Clin Exp Pharmacol Physiol. 2010 Jan;37(1):62-8. doi: 10.1111/j.1440-1681.2009.05227.x. 19566844 Chinkes DL: Methods for measuring tissue protein breakdown rate in vivo. Curr Opin Clin Nutr Metab Care. 2005 Sep;8(5):534-7. doi: 10.1097/01.mco.0000170754.25372.37. 16079625