Human Metabolome Database Version 3.5

Showing metabocard for L-Histidine (HMDB00177)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-07-12 10:32:01 -0600
HMDB ID HMDB00177
Secondary Accession Numbers
  • HMDB03412
Metabolite Identification
Common Name L-Histidine
Description Histidine is an alpha-amino acid with an imidazole functional group. It is one of the 22 proteinogenic amino acids. Histidine was first isolated by German physician Albrecht Kossel in 1896. Histidine is an essential amino acid in humans and other mammals. It was initially thought that it was only essential for infants, but longer-term studies established that it is also essential for adults. Infants four to six months old require 33 mg/kg of histidine. It is not clear how adults make small amounts of histidine, and dietary sources probably account for most of the histidine in the body. Histidine is a precursor for histamine and carnosine biosynthesis. Inborn errors of histidine metabolism exist and are marked by increased histidine levels in the blood. Elevated blood histidine is accompanied by a wide range of symptoms, from mental and physical retardation to poor intellectual functioning, emotional instability, tremor, ataxia and psychosis. Histidine and other imidazole compounds have anti-oxidant, anti-inflammatory and anti-secretory properties (PMID: 9605177 Link_out). The efficacy of L-histidine in protecting inflamed tissue is attributed to the capacity of the imidazole ring to scavenge reactive oxygen species (ROS) generated by cells during acute inflammatory response (PMID: 9605177 Link_out). Histidine, when administered in therapeutic quantities is able to inhibit cytokines and growth factors involved in cell and tissue damage (US patent 6150392). Histidine in medical therapies has its most promising trials in rheumatoid arthritis where up to 4.5 g daily have been used effectively in severely affected patients. Arthritis patients have been found to have low serum histidine levels, apparently because of very rapid removal of histidine from their blood (PMID: 1079527 Link_out). Other patients besides arthritis patients that have been found to be low in serum histidine are those with chronic renal failure. Urinary levels of histidine are reduced in pediatric patients with pneumonia. (PMID: 2084459 Link_out). Asthma patients exhibit increased serum levels of histidine over normal controls (PMID: 23517038 Link_out). Serum histidine levels are lower and are negatively associated with inflammation and oxidative stress in obese women (PMID: 23361591 Link_out). Histidine supplementation has been shown to reduce insulin resistance, reduce BMI and fat mass and suppress inflammation and oxidative stress in obese women with metabolic syndrome. Histidine appears to suppress pro-inflammatory cytokine expression, possibly via the NF-κB pathway, in adipocytes (PMID: 23361591 Link_out). Low plasma concentrations of histidine are associated with protein-energy wasting, inflammation, oxidative stress, and greater mortality in chronic kidney disease patients (PMID: 18541578 Link_out). Histidine may have many other possible functions because it is the precursor of the ubiquitous neurohormone-neurotransmitter histamine. Histidine increases histamine in the blood and probably in the brain. Low blood histamine with low serum histidine occurs in rheumatoid arthritis patients. Low blood histamine also occurs in some manic, schizophrenic, high copper and hyperactive groups of psychiatric patients. Histidine is a useful therapy in all patients with low histamine levels. (http://www.dcnutrition.com ).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (S)-1H-Imidazole-4-alanine
  2. (S)-2-Amino-3-(4-imidazolyl)propionsaeure
  3. (S)-4-(2-Amino-2-carboxyethyl)imidazole
  4. (S)-a-Amino-1H-imidazole-4-propanoate
  5. (S)-a-Amino-1H-imidazole-4-propanoic acid
  6. (S)-alpha-Amino-1H-imidazole-4-propanoate
  7. (S)-alpha-Amino-1H-imidazole-4-propanoic acid
  8. (S)-alpha-Amino-1H-imidazole-4-propionate
  9. (S)-alpha-Amino-1H-imidazole-4-propionic acid
  10. (S)-Histidine
  11. (S)1H-Imidazole-4-alanine
  12. 3-(1H-Imidazol-4-yl)-L-Alanine
  13. Amino-1H-imidazole-4-propanoate
  14. Amino-1H-imidazole-4-propanoic acid
  15. Amino-4-imidazoleproprionate
  16. Amino-4-imidazoleproprionic acid
  17. Glyoxaline-5-alanine
  18. His
  19. Histidine
  20. L-(-)-Histidine
Chemical Formula C6H9N3O2
Average Molecular Weight 155.1546
Monoisotopic Molecular Weight 155.069476547
IUPAC Name (2S)-2-amino-3-(1H-imidazol-4-yl)propanoic acid
Traditional IUPAC Name histidine
CAS Registry Number 71-00-1
SMILES N[C@@H](CC1=CNC=N1)C(O)=O
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
InChI Key HNDVDQJCIGZPNO-YFKPBYRVSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aromatic Heteromonocyclic Compounds
  • alpha-amino acid(ChEBI)
  • imidazoles(ChEBI)
Substituents
  • Aminoimidazole
  • Carboxylic Acid
  • Imidazole
  • Imidazolyl Carboxylic Acid Derivative
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Drug
  • Food
Biofunction
  • Component of Aminoacyl-tRNA biosynthesis
  • Component of Histidine metabolism
  • Component of Nitrogen metabolism
  • Essential amino acid
  • Essential amino acids
  • semi-essential amino acids
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
State Solid
Experimental Properties
Property Value Reference
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)
Predicted Properties
Property Value Source
Water Solubility 71.3 g/L ALOGPS
LogP -2.67 ALOGPS
LogP -3.3 ChemAxon
LogS -0.34 ALOGPS
pKa (strongest acidic) 1.85 ChemAxon
pKa (strongest basic) 9.25 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 92 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 37.49 ChemAxon
Polarizability 14.92 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
13C NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • All Tissues
  • Prostate
Pathways
Name SMPDB Link KEGG Link
Histidine Metabolism SMP00044 map00340 Link_out
Ammonia Recycling SMP00009 map00910 Link_out
Transcription/Translation SMP00019 Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
75.0 +/- 20.0 uM Newborn (0-30 days old) Not Specified Normal
  • Geigy Scient...
Blood Detected and Quantified
86.0 +/- 10.0 uM Children (1-13 year old) Male Normal
  • Geigy Scient...
Blood Detected and Quantified
89.0 +/- 11.0 uM Adult (>18 years old) Male Normal
  • Geigy Scient...
Blood Detected and Quantified
83.0 +/- 14.0 uM Adult (>18 years old) Female Normal
  • Geigy Scient...
Blood Detected and Quantified
143.1 +/- 27.3 uM Adult (>18 years old) Not Specified Normal
Blood Detected and Quantified
88.00 (56.00-120.00) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
82.0 (72.0-92.0) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
131.2 +/- 37.3 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
14.0 +/- 8.0 uM Not Specified Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
20.7 +/- 7.5 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
16.8 +/- 2.7 uM Adult (>18 years old) Male Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
18.6 +/- 3.3 uM Adult (>18 years old) Female Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
16.4 +/- 6.1 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
13.00 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
10.9 (10.4-11.4) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
11.9 +/- 1.7 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Saliva Detected and Quantified
>10 uM Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected and Quantified
101.9 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
25.79-212.81 umol/mmol creatinine Adult (>18 years old) Both Normal
  • David F. Put...
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected and Quantified
87.2 (23.0-151.0) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
47.12 umol/mmol creatinine Adult (>18 years old) Male Normal
  • Shaykhutdino...
Urine Detected and Quantified
0.0036 - 0.0376 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
43 (17-90) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
2.2 (1.18-3.4) umol/mmol creatinine Newborn (0-30 days old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
31.0 +/- 15.0 umol/mmol creatinine Children (1-13 year old) Male Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
85.0 +/- 33.0 umol/mmol creatinine Adult (>18 years old) Male Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
62.0 +/- 28.0 umol/mmol creatinine Adult (>18 years old) Female Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
60.75 +/- 27.45 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
45.6 (21.7-71.5) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
88 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
194.90 +/- 144.31 umol/mmol creatinine Infant (0-1 year old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 46.1 +/- 17.5 uM Adult (>18 years old) Not Specified Heart Transplant
Blood Detected and Quantified 885.00 (290.00-1420.00) uM Children (1-13 year old) Both Histidinemia
Blood Detected and Quantified 116.68 +/- 18.15 uM Elderly (>65 years old) Both Alzheimer's disease
Blood Detected and Quantified 67.0 (64.0-70.0) uM Adult (>18 years old) Both Dengue fever
Blood Detected and Quantified 80.5 +/- 4.2 uM Adult (>18 years old) Both Comment Epilepsy
Blood Detected and Quantified 107.0 +/- 6.5 uM Adult (>18 years old) Both Comment Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 21.4 +/- 6.6 uM Children (1-13 year old) Not Specified Leukemia
Cerebrospinal Fluid (CSF) Detected and Quantified 10.3 +/- 3.7 uM Children (1-13 year old) Not Specified Comment Leukemia
Cerebrospinal Fluid (CSF) Detected and Quantified 95.00 (48.00-142.00) uM Children (1-13 year old) Both Histidinemia
Cerebrospinal Fluid (CSF) Detected and Quantified 130.0 uM Adult (>18 years old) Both Histidinemia
Cerebrospinal Fluid (CSF) Detected and Quantified 14.4 +/- 6.32 uM Adult (>18 years old) Both Probable Alzheimer's diesease
Urine Detected and Quantified 0.0033 - 0.0186 umol/mmol creatinine Adult (>18 years old) Both ADPKD
Urine Detected and Quantified 30.5 +/- 4.3 umol/mmol creatinine Adult (>18 years old) Both Alzheimer's disease
Urine Detected and Quantified 1696.84 (339.37-3054.30) umol/mmol creatinine Children (1-13 year old) Both Histidinuria
Urine Detected and Quantified 105.3 +/- 12.7 umol/mmol creatinine Adult (>18 years old) Both 3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency
Urine Detected and Quantified 65.5 +/- 11.3 umol/mmol creatinine Adult (>18 years old) Both 3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency
Urine Detected and Quantified 52.9 +/- 12.5 umol/mmol creatinine Adult (>18 years old) Both Arginosuccinic aciduria
Urine Detected and Quantified 154.3 +/- 13.7 umol/mmol creatinine Adult (>18 years old) Both Propionic acidemia
Urine Detected and Quantified 52 +/- 29 umol/mmol creatinine Adult (>18 years old) Both Tyrosinemia I
Urine Detected and Quantified 37.9 +/- 9.8 umol/mmol creatinine Adult (>18 years old) Both Tyrosinemia I
Urine Detected and Quantified 62.6 +/- 12.3 umol/mmol creatinine Adult (>18 years old) Both Phenylketonuria
Urine Detected and Quantified 68 +/- 19.9 umol/mmol creatinine Adult (>18 years old) Both Phenylketonuria
Urine Detected and Quantified 171.8 +/- 4.3 umol/mmol creatinine Adult (>18 years old) Both Maple syrup urine disease
Urine Detected and Quantified 180.1 +/- 12.4 umol/mmol creatinine Adult (>18 years old) Both Aminoaciduria
Associated Disorders and Diseases
Disease References
Dengue fever
  • Klassen P, Furst P, Schulz C, Mazariegos M, Solomons NW: Plasma free amino acid concentrations in healthy Guatemalan adults and in patients with classic dengue. Am J Clin Nutr. 2001 Mar;73(3):647-52. Pubmed: 11237944 Link_out
      Epilepsy
      • Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292 Link_out
          Histidinemia
          • Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51. Pubmed: 7729054 Link_out
            Leukemia
            • Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239 Link_out
                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: 17031479 Link_out
                    Associated OMIM IDs
                    DrugBank ID DB00117 Link_out
                    DrugBank Metabolite ID Not Available
                    Phenol Explorer Compound ID Not Available
                    Phenol Explorer Metabolite ID Not Available
                    FoodDB ID FDB011856
                    KNApSAcK ID C00001363 Link_out
                    Chemspider ID 6038 Link_out
                    KEGG Compound ID C00135 Link_out
                    BioCyc ID HIS Link_out
                    BiGG ID 33985 Link_out
                    Wikipedia Link L-Histidine Link_out
                    NuGOwiki Link HMDB00177 Link_out
                    Metagene Link HMDB00177 Link_out
                    METLIN ID 21 Link_out
                    PubChem Compound 6274 Link_out
                    PDB ID 1KAH Link_out
                    ChEBI ID 15971 Link_out
                    References
                    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.
                    Material Safety Data Sheet (MSDS) Download (PDF)
                    General References
                    1. Mukerji SK, Pimstone NR, Gandhi SN, Tan KT: Biochemical diagnosis and monitoring therapeutic modulation of disease activity in an unusual case of congenital erythropoietic porphyria. Clin Chem. 1985 Dec;31(12):1946-51. Pubmed: 4064282 Link_out
                    2. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239 Link_out
                    3. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. Pubmed: 12297216 Link_out
                    4. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292 Link_out
                    5. Xiao B, Jing C, Kelly G, Walker PA, Muskett FW, Frenkiel TA, Martin SR, Sarma K, Reinberg D, Gamblin SJ, Wilson JR: Specificity and mechanism of the histone methyltransferase Pr-Set7. Genes Dev. 2005 Jun 15;19(12):1444-54. Epub 2005 Jun 2. Pubmed: 15933069 Link_out
                    6. Churchill D, Yacoub JM, Siu KP, Symes A, Gault MH: Toxic nephropathy after low-dose methoxyflurane anesthesia: drug interaction with secobarbital? Can Med Assoc J. 1976 Feb 21;114(4):326-8, 333. Pubmed: 1253070 Link_out
                    7. Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51. Pubmed: 7729054 Link_out
                    8. Sieja K, Stanosz S, von Mach-Szczypinski J, Olewniczak S, Stanosz M: Concentration of histamine in serum and tissues of the primary ductal breast cancers in women. Breast. 2005 Jun;14(3):236-41. Epub 2005 Jan 21. Pubmed: 15927833 Link_out
                    9. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436 Link_out
                    10. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685 Link_out
                    11. Masini E, Fabbroni V, Giannini L, Vannacci A, Messerini L, Perna F, Cortesini C, Cianchi F: Histamine and histidine decarboxylase up-regulation in colorectal cancer: correlation with tumor stage. Inflamm Res. 2005 Apr;54 Suppl 1:S80-1. Pubmed: 15928846 Link_out
                    12. Klassen P, Furst P, Schulz C, Mazariegos M, Solomons NW: Plasma free amino acid concentrations in healthy Guatemalan adults and in patients with classic dengue. Am J Clin Nutr. 2001 Mar;73(3):647-52. Pubmed: 11237944 Link_out
                    13. Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75. Pubmed: 6696735 Link_out
                    14. Xiao YP, Han CB, Mao XY, Li JY, Xu L, Ren CS, Xin Y: Relationship between abnormality of FHIT gene and EBV infection in gastric cancer. World J Gastroenterol. 2005 Jun 7;11(21):3212-6. Pubmed: 15929169 Link_out
                    15. Mason AB, Halbrooks PJ, James NG, Connolly SA, Larouche JR, Smith VC, MacGillivray RT, Chasteen ND: Mutational analysis of C-lobe ligands of human serum transferrin: insights into the mechanism of iron release. Biochemistry. 2005 Jun 7;44(22):8013-21. Pubmed: 15924420 Link_out
                    16. Janknecht R, Hipskind RA, Houthaeve T, Nordheim A, Stunnenberg HG: Identification of multiple SRF N-terminal phosphorylation sites affecting DNA binding properties. EMBO J. 1992 Mar;11(3):1045-54. Pubmed: 1547771 Link_out
                    17. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. Pubmed: 6198473 Link_out
                    18. 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. Pubmed: 19212411 Link_out
                    19. Peterson JW, Boldogh I, Popov VL, Saini SS, Chopra AK: Anti-inflammatory and antisecretory potential of histidine in Salmonella-challenged mouse small intestine. Lab Invest. 1998 May;78(5):523-34. Pubmed: 9605177 Link_out
                    20. Gerber DA: Low free serum histidine concentration in rheumatoid arthritis. A measure of disease activity. J Clin Invest. 1975 Jun;55(6):1164-73. Pubmed: 1079527 Link_out
                    21. Hemler RJ, Hoogeveen JH, Kraaier V, Van Huffelen AC, Wieneke GH, Hijman R, Glerum JH: A pharmacological model of cerebral ischemia. The effects of indomethacin on cerebral blood flow velocity, quantitative EEG and cognitive functions. Methods Find Exp Clin Pharmacol. 1990 Nov;12(9):641-3. Pubmed: 2084459 Link_out
                    22. Feng RN, Niu YC, Sun XW, Li Q, Zhao C, Wang C, Guo FC, Sun CH, Li Y: Histidine supplementation improves insulin resistance through suppressed inflammation in obese women with the metabolic syndrome: a randomised controlled trial. Diabetologia. 2013 May;56(5):985-94. doi: 10.1007/s00125-013-2839-7. Epub 2013 Jan 30. Pubmed: 23361591 Link_out
                    23. Watanabe M, Suliman ME, Qureshi AR, Garcia-Lopez E, Barany P, Heimburger O, Stenvinkel P, Lindholm B: Consequences of low plasma histidine in chronic kidney disease patients: associations with inflammation, oxidative stress, and mortality. Am J Clin Nutr. 2008 Jun;87(6):1860-6. Pubmed: 18541578 Link_out
                    24. Jung J, Kim SH, Lee HS, Choi GS, Jung YS, Ryu DH, Park HS, Hwang GS: Serum metabolomics reveals pathways and biomarkers associated with asthma pathogenesis. Clin Exp Allergy. 2013 Apr;43(4):425-33. doi: 10.1111/cea.12089. Pubmed: 23517038 Link_out
                    25. Effective method for the amelioration and prevention of tissue and cellular damage Link_out

                    Enzymes
                    Name: Aromatic-L-amino-acid decarboxylase
                    Reactions:
                    L-Histidine unknown Histamine + Carbon dioxide details
                    Gene Name: DDC
                    Uniprot ID: P20711 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: Beta-Ala-His dipeptidase
                    Reactions: Not Available
                    Gene Name: CNDP1
                    Uniprot ID: Q96KN2 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: Protein arginine N-methyltransferase 3
                    Reactions: Not Available
                    Gene Name: PRMT3
                    Uniprot ID: O60678 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: Probable histidine--tRNA ligase, mitochondrial
                    Reactions:
                    Adenosine triphosphate + L-Histidine + tRNA(His) unknown Adenosine monophosphate + Pyrophosphate + L-histidyl-tRNA(His) details
                    Adenosine triphosphate + L-Histidine + tRNA(His) unknown Adenosine monophosphate + Pyrophosphate + L-Histidyl-tRNA(His) details
                    Gene Name: HARS2
                    Uniprot ID: P49590 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: Histidine--tRNA ligase, cytoplasmic
                    Reactions:
                    Adenosine triphosphate + L-Histidine + tRNA(His) unknown Adenosine monophosphate + Pyrophosphate + L-histidyl-tRNA(His) details
                    Adenosine triphosphate + L-Histidine + tRNA(His) unknown Adenosine monophosphate + Pyrophosphate + L-Histidyl-tRNA(His) details
                    Gene Name: HARS
                    Uniprot ID: P12081 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: Histidine ammonia-lyase
                    Reactions:
                    L-Histidine unknown Urocanic acid + Ammonia details
                    Gene Name: HAL
                    Uniprot ID: P42357 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: Histidine decarboxylase
                    Reactions:
                    L-Histidine unknown Histamine + CO(2) details
                    L-Histidine unknown Histamine + Carbon dioxide details
                    Gene Name: HDC
                    Uniprot ID: P19113 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: Carnosine synthase 1
                    Reactions:
                    Adenosine triphosphate + L-Histidine + Beta-Alanine unknown ADP + Phosphoric acid + Carnosine details
                    Adenosine triphosphate + L-Histidine + Beta-Alanine unknown Adenosine monophosphate + Pyrophosphate + Carnosine details
                    Adenosine triphosphate + L-Histidine + Gamma-Aminobutyric acid unknown Adenosine monophosphate + Pyrophosphate + Homocarnosine details
                    Gene Name: CARNS1
                    Uniprot ID: A5YM72 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: HemK methyltransferase family member 1
                    Reactions:
                    L-Histidine + S-Adenosylmethionine unknown 3-Methylhistidine + S-Adenosylhomocysteine details
                    Gene Name: HEMK1
                    Uniprot ID: Q9Y5R4 Link_out
                    Name: Methyltransferase-like protein 2B
                    Reactions:
                    L-Histidine + S-Adenosylmethionine unknown 3-Methylhistidine + S-Adenosylhomocysteine details
                    Gene Name: METTL2B
                    Uniprot ID: Q6P1Q9 Link_out
                    Name: Methyltransferase-like protein 6
                    Reactions:
                    L-Histidine + S-Adenosylmethionine unknown 3-Methylhistidine + S-Adenosylhomocysteine details
                    Gene Name: METTL6
                    Uniprot ID: Q8TCB7 Link_out
                    Name: Uncharacterized methyltransferase WBSCR22
                    Reactions:
                    L-Histidine + S-Adenosylmethionine unknown 3-Methylhistidine + S-Adenosylhomocysteine details
                    Gene Name: WBSCR22
                    Uniprot ID: O43709 Link_out
                    Transporters
                    Name: Sodium-coupled neutral amino acid transporter 3
                    Reactions: Not Available
                    Gene Name: SLC38A3
                    Uniprot ID: Q99624 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: Monocarboxylate transporter 10
                    Reactions: Not Available
                    Gene Name: SLC16A10
                    Uniprot ID: Q8TF71 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA