Chemical Formula: C6H9N3O2

Chemical Formula C6H9N3O2

Found 98 metabolite its formula value is C6H9N3O2

L-Histidine

(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid

C6H9N3O2 (155.0694734)


Histidine (His), also known as L-histidine, is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. Histidine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Histidine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, positively charged or basic amino acid. Histidine is a unique amino acid with an imidazole functional group. The acid-base properties of the imidazole side chain are relevant to the catalytic mechanism of many enzymes such as proteases. In catalytic triads, the basic nitrogen of histidine abstracts a proton from serine, threonine, or cysteine to activate it as a nucleophile. In a histidine proton shuttle, histidine is used to quickly shuttle protons. It can do this by abstracting a proton with its basic nitrogen to make a positively charged intermediate and then use another molecule to extract the proton from its acidic nitrogen. Histidine forms complexes with many metal ions. The imidazole sidechain of the histidine residue commonly serves as a ligand in metalloproteins. 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, including histidinemia, maple syrup urine disease, propionic acidemia, and tyrosinemia I, 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 ). 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 ). 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 ). 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 ). Asthma patients exhibit increased serum levels of histidine over normal controls (PMID: 23517038 ). Serum histidine levels are lower and are negatively associated with inflammation and oxidative stress in obese women (PMID: 23361591 ). 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 ). Low plasma concentrations of histidine are associated with protein-energy... [Spectral] L-Histidine (exact mass = 155.06948) and L-Lysine (exact mass = 146.10553) and L-Arginine (exact mass = 174.11168) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] L-Histidine (exact mass = 155.06948) and L-Arginine (exact mass = 174.11168) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Acquisition and generation of the data is financially supported in part by CREST/JST. Flavouring ingredient; dietary supplement, nutrient L-Histidine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=71-00-1 (retrieved 2024-07-01) (CAS RN: 71-00-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport.

   

3-(Pyrazol-1-yl)-L-alanine

alpha-amino-beta-(Pyrazolyl-N)propionic acid

C6H9N3O2 (155.0694734)


L-2-Amino-3-(1-pyrazolyl)propanoic acid is found in fruits. L-2-Amino-3-(1-pyrazolyl)propanoic acid is a amino acid present in seeds of Citrullus vulgaris (watermelon Amino acid present in seeds of Citrullus vulgaris (watermelon). L-2-Amino-3-(1-pyrazolyl)propanoic acid is found in fruits.

   

D-Histidine

2-amino-3-(1H-imidazol-5-yl)propanoic acid

C6H9N3O2 (155.06947340000002)


   

D-HISTIDINE

D-HISTIDINE

C6H9N3O2 (155.06947340000002)


An optically active form of histidine having D-configuration. D-Histidine is an enantiomer of?L-histidine (HY-N0832).?L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of?mitochondrial glutamine transport[1].

   

HISTIDINE

L-Histidine Base

C6H9N3O2 (155.06947340000002)


L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport.

   
   
   
   

2-amino-3-(1H-imidazol-2-yl)propanoic acid

2-amino-3-(1H-imidazol-2-yl)propanoic acid

C6H9N3O2 (155.06947340000002)


   

Histidine

L-Histidine Base

C6H9N3O2 (155.06947340000002)


An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3. The L-enantiomer of the amino acid histidine. Histidine (symbol His or H)[2] is an essential amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated –NH3+ form under biological conditions), a carboxylic acid group (which is in the deprotonated –COO− form under biological conditions), and an imidazole side chain (which is partially protonated), classifying it as a positively charged amino acid at physiological pH. Initially thought essential only for infants, it has now been shown in longer-term studies to be essential for adults also.[3] It is encoded by the codons CAU and CAC. Histidine was first isolated by Albrecht Kossel and Sven Gustaf Hedin in 1896.[4] The name stems from its discovery in tissue, from ἱστός histós "tissue".[2] It is also a precursor to histamine, a vital inflammatory agent in immune responses. The acyl radical is histidyl. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.046 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.045 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.043 L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport.

   

L-Histidine

L-Histidine

C6H9N3O2 (155.06947340000002)


MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; HNDVDQJCIGZPNO_STSL_0107_Histidine_8000fmol_180430_S2_LC02_MS02_142; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport.

   
   

L-3-PYRAZOL-1-YL-ALANINE

alpha-amino-beta-(Pyrazolyl-N)propionic acid

C6H9N3O2 (155.06947340000002)


   

1H-Imidazole-4-carboxamide,5-hydroxy-N,N-dimethyl-(9CI)

1H-Imidazole-4-carboxamide,5-hydroxy-N,N-dimethyl-(9CI)

C6H9N3O2 (155.06947340000002)


   

2H-1,2,3-Triazole-4-carboxylicacid,2-ethyl-,methylester(9CI)

2H-1,2,3-Triazole-4-carboxylicacid,2-ethyl-,methylester(9CI)

C6H9N3O2 (155.06947340000002)


   

1H-1,2,3-Triazole-5-carboxylicacid,1-ethyl-,methylester(9CI)

1H-1,2,3-Triazole-5-carboxylicacid,1-ethyl-,methylester(9CI)

C6H9N3O2 (155.06947340000002)


   

Urea, N-methyl-N-(5-methyl-3-isoxazolyl)- (9CI)

Urea, N-methyl-N-(5-methyl-3-isoxazolyl)- (9CI)

C6H9N3O2 (155.06947340000002)


   
   

ethyl 2-(1h-1,2,4-triazol-1-yl)acetate

ethyl 2-(1h-1,2,4-triazol-1-yl)acetate

C6H9N3O2 (155.06947340000002)


   

Methyl (3-amino-1H-pyrazol-1-yl)acetate

Methyl (3-amino-1H-pyrazol-1-yl)acetate

C6H9N3O2 (155.06947340000002)


   

Methyl 5-amino-1-methyl-1H-pyrazole-3-carboxylate

Methyl 5-amino-1-methyl-1H-pyrazole-3-carboxylate

C6H9N3O2 (155.06947340000002)


   
   

Acetamide,2-cyano-N-methyl-N-[(methylamino)carbonyl]-

Acetamide,2-cyano-N-methyl-N-[(methylamino)carbonyl]-

C6H9N3O2 (155.06947340000002)


   

(R)-3-Azido-4,4-dimethyldihydrofuran-2(3H)-one

(R)-3-Azido-4,4-dimethyldihydrofuran-2(3H)-one

C6H9N3O2 (155.06947340000002)


   

5-Oxazolecarboxylic acid,2,4-dimethyl-,hydrazide

5-Oxazolecarboxylic acid,2,4-dimethyl-,hydrazide

C6H9N3O2 (155.06947340000002)


   

METHYL 5-AMINO-1-METHYL-1H-PYRAZOLE-4-CARBOXYLATE

METHYL 5-AMINO-1-METHYL-1H-PYRAZOLE-4-CARBOXYLATE

C6H9N3O2 (155.06947340000002)


   

(3,5-dimethyl-1,2-oxazol-4-yl)urea

(3,5-dimethyl-1,2-oxazol-4-yl)urea

C6H9N3O2 (155.06947340000002)


   

(3,4-dimethyl-1,2-oxazol-5-yl)urea

(3,4-dimethyl-1,2-oxazol-5-yl)urea

C6H9N3O2 (155.06947340000002)


   
   

Uracil,5-amino-1,6-dimethyl- (1CI)

Uracil,5-amino-1,6-dimethyl- (1CI)

C6H9N3O2 (155.06947340000002)


   

2-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)acetic acid

2-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)acetic acid

C6H9N3O2 (155.06947340000002)


   

ETHYL 1-METHYL-1H-1,2,3-TRIAZOLE-4-CARBOXYLATE

ETHYL 1-METHYL-1H-1,2,3-TRIAZOLE-4-CARBOXYLATE

C6H9N3O2 (155.06947340000002)


   

1H-1,2,4-Triazole-5-carboxaldehyde, 1-(2-methoxyethyl)- (9CI)

1H-1,2,4-Triazole-5-carboxaldehyde, 1-(2-methoxyethyl)- (9CI)

C6H9N3O2 (155.06947340000002)


   

Urea, N-methyl-N-(3-methyl-5-isoxazolyl)- (9CI)

Urea, N-methyl-N-(3-methyl-5-isoxazolyl)- (9CI)

C6H9N3O2 (155.06947340000002)


   

Urea, N-3-isoxazolyl-N,N-dimethyl- (9CI)

Urea, N-3-isoxazolyl-N,N-dimethyl- (9CI)

C6H9N3O2 (155.06947340000002)


   

METHYL3-AMINO-1-METHYLPYRAZOLE-5-CARBOXYLATE

METHYL3-AMINO-1-METHYLPYRAZOLE-5-CARBOXYLATE

C6H9N3O2 (155.06947340000002)


   
   

1H-Imidazole-4-carboxamide,5-hydroxy-N,1-dimethyl-

1H-Imidazole-4-carboxamide,5-hydroxy-N,1-dimethyl-

C6H9N3O2 (155.06947340000002)


   
   

2-(DIMETHYLAMINO)-4,6-PYRIMIDINEDIOL

2-(DIMETHYLAMINO)-4,6-PYRIMIDINEDIOL

C6H9N3O2 (155.06947340000002)


   
   

methyl 2-amino-3-methyl-imidazole-4-carboxylate

methyl 2-amino-3-methyl-imidazole-4-carboxylate

C6H9N3O2 (155.06947340000002)


   

5-(2-aminoethyl)pyrimidine-2,4(1H,3H)-dione

5-(2-aminoethyl)pyrimidine-2,4(1H,3H)-dione

C6H9N3O2 (155.06947340000002)


   
   
   

Ethyl 1-Methyl-1H-1,2,3-triazole-5-carboxylate

Ethyl 1-Methyl-1H-1,2,3-triazole-5-carboxylate

C6H9N3O2 (155.06947340000002)


   

1H-Imidazole-2-carboxylicacid,4-(2-aminoethyl)-(9CI)

1H-Imidazole-2-carboxylicacid,4-(2-aminoethyl)-(9CI)

C6H9N3O2 (155.06947340000002)


   

2-Isopropyl-4-nitro-1H-imidazole

2-Isopropyl-4-nitro-1H-imidazole

C6H9N3O2 (155.06947340000002)


   

2,4-Dimethoxy-6-methyl-1,3,5-triazine

2,4-Dimethoxy-6-methyl-1,3,5-triazine

C6H9N3O2 (155.06947340000002)


   

Ethyl4-amino-1H-pyrazole-5-carboxylate

Ethyl4-amino-1H-pyrazole-5-carboxylate

C6H9N3O2 (155.06947340000002)


   

2-Cyano-N-(ethylcarbamoyl)acetamide

2-Cyano-N-(ethylcarbamoyl)acetamide

C6H9N3O2 (155.06947340000002)


   

1-Isopropyl-4-nitro-1H-pyrazole

1-Isopropyl-4-nitro-1H-pyrazole

C6H9N3O2 (155.06947340000002)


   

METHYL-3-(1H-1,2,4-TRIAZOLE-1-YL)-PROPIONATE

METHYL-3-(1H-1,2,4-TRIAZOLE-1-YL)-PROPIONATE

C6H9N3O2 (155.06947340000002)


   

2,4(1H,3H)-Pyrimidinedione,5-amino-1,3-dimethyl-

2,4(1H,3H)-Pyrimidinedione,5-amino-1,3-dimethyl-

C6H9N3O2 (155.06947340000002)


   

2-AMINO-1H-IMIDAZOLE-1-PROPANOIC ACID

2-AMINO-1H-IMIDAZOLE-1-PROPANOIC ACID

C6H9N3O2 (155.06947340000002)


   

1H-Imidazole-1-aceticacid,4-amino-,methylester(9CI)

1H-Imidazole-1-aceticacid,4-amino-,methylester(9CI)

C6H9N3O2 (155.06947340000002)


   

2-Amino-4,6-dimethoxypyrimidine

2-Amino-4,6-dimethoxypyrimidine

C6H9N3O2 (155.06947340000002)


   
   

1H-Pyrazole-4-aceticacid,alpha-amino-1-methyl-(9CI)

1H-Pyrazole-4-aceticacid,alpha-amino-1-methyl-(9CI)

C6H9N3O2 (155.06947340000002)


   
   

6-amino-1-ethylpyrimidine-2,4-dione

6-amino-1-ethylpyrimidine-2,4-dione

C6H9N3O2 (155.06947340000002)


   

1H-Pyrazole-5-carboxylicacid,1-amino-3-methyl-,methylester(9CI)

1H-Pyrazole-5-carboxylicacid,1-amino-3-methyl-,methylester(9CI)

C6H9N3O2 (155.06947340000002)


   

Pyrazine,2-amino-3,5-dimethoxy- (8CI)

Pyrazine,2-amino-3,5-dimethoxy- (8CI)

C6H9N3O2 (155.06947340000002)


   

1-ethyl-2-methyl-4-nitroimidazole

1-ethyl-2-methyl-4-nitroimidazole

C6H9N3O2 (155.06947340000002)


   

2-METHYL-2-(1H-1,2,4-TRIAZOL-1-YL)PROPANOIC ACID

2-METHYL-2-(1H-1,2,4-TRIAZOL-1-YL)PROPANOIC ACID

C6H9N3O2 (155.06947340000002)


   

Ethyl 2-amino-1H-imidazole-5-carboxylate

Ethyl 2-amino-1H-imidazole-5-carboxylate

C6H9N3O2 (155.06947340000002)


   

Ethyl 3-amino-4-pyrazolecarboxylate

Ethyl 3-amino-4-pyrazolecarboxylate

C6H9N3O2 (155.06947340000002)


   
   

ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate

ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate

C6H9N3O2 (155.06947340000002)


   
   

1H-1,2,3-Triazole-4-carboxylicacid,1-ethyl-,methylester(9CI)

1H-1,2,3-Triazole-4-carboxylicacid,1-ethyl-,methylester(9CI)

C6H9N3O2 (155.06947340000002)


   

3-amino-3-(1h-imidazol-2-yl)-propionic acid

3-amino-3-(1h-imidazol-2-yl)-propionic acid

C6H9N3O2 (155.06947340000002)


   

Ethyl 5-amino-1H-pyrazole-3-carboxylate

Ethyl 5-amino-1H-pyrazole-3-carboxylate

C6H9N3O2 (155.06947340000002)


   

5-amino-3-ethyl-4-Isoxazole carboxamide

5-amino-3-ethyl-4-Isoxazole carboxamide

C6H9N3O2 (155.06947340000002)


   

ETHYL5-AMINO-1H-PYRAZOLE-4-CARBOXYLATE

ETHYL5-AMINO-1H-PYRAZOLE-4-CARBOXYLATE

C6H9N3O2 (155.06947340000002)


   

1,3,5-Trimethyl-4-nitro-1H-pyrazole

1,3,5-Trimethyl-4-nitro-1H-pyrazole

C6H9N3O2 (155.06947340000002)


   

6-AMINO-2-METHOXY-5-METHYLPYRIMIDIN-4(3H)-ONE

6-AMINO-2-METHOXY-5-METHYLPYRIMIDIN-4(3H)-ONE

C6H9N3O2 (155.06947340000002)


   
   

Ethyl 5-aMino-1H-pyrazole-4-carboxylate

Ethyl 5-aMino-1H-pyrazole-4-carboxylate

C6H9N3O2 (155.06947340000002)


   
   

Ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate

Ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate

C6H9N3O2 (155.06947340000002)


   

(S)-2-amino-3-(imidazol-1-yl)propanoic acid

(S)-2-amino-3-(imidazol-1-yl)propanoic acid

C6H9N3O2 (155.06947340000002)


   

5-AMINO-1-ETHYL-PYRAZOLE-4-CARBOXYLIC ACID

5-AMINO-1-ETHYL-PYRAZOLE-4-CARBOXYLIC ACID

C6H9N3O2 (155.06947340000002)


   

2-METHYL-3-[1,2,4]TRIAZOL-1-YL-PROPIONIC ACID

2-METHYL-3-[1,2,4]TRIAZOL-1-YL-PROPIONIC ACID

C6H9N3O2 (155.06947340000002)


   

METHYL 4-AMINO-1-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE

METHYL 4-AMINO-1-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE

C6H9N3O2 (155.06947340000002)


   
   

Ethyl 4-amino-1H-imidazole-5-carboxylate

Ethyl 4-amino-1H-imidazole-5-carboxylate

C6H9N3O2 (155.06947340000002)


   

3-(N,N-Dimethylamino)-D-alanine

3-(N,N-Dimethylamino)-D-alanine

C6H9N3O2 (155.06947340000002)


   

(2S)-2-azaniumyl-3-(1H-imidazol-5-yl)propanoate

(2S)-2-azaniumyl-3-(1H-imidazol-5-yl)propanoate

C6H9N3O2 (155.06947340000002)


   

(2R)-2-azaniumyl-3-(1H-imidazol-4-yl)propanoate

(2R)-2-azaniumyl-3-(1H-imidazol-4-yl)propanoate

C6H9N3O2 (155.06947340000002)


   

(2S)-2-ammonio-3-(1H-pyrazol-1-yl)propanoate

(2S)-2-ammonio-3-(1H-pyrazol-1-yl)propanoate

C6H9N3O2 (155.06947340000002)


   

L-histidine zwitterion

L-histidine zwitterion

C6H9N3O2 (155.06947340000002)


Zwitterionic form of L-histidine having an anionic carboxy group and a protonated alpha-amino group.

   

2-amino-3-(1H-pyrazol-1-yl)propanoic acid

(R)-3-AMINO-3-(4-BROMOPHENYL)PROPIONICACID

C6H9N3O2 (155.06947340000002)


   

3-(pyrazol-1-yl)-L-alanine zwitterion

3-(pyrazol-1-yl)-L-alanine zwitterion

C6H9N3O2 (155.06947340000002)


Zwitterionic form of 3-(pyrazol-1-yl)-L-alanine having an anionic carboxy group and a protonated alpha-amino group; major species at pH 7.3.

   

D-histidine zwitterion

D-histidine zwitterion

C6H9N3O2 (155.06947340000002)


A polar amino acid zwitterion restulting from the transfer of a proton from the carboxy group to the alpha-amino group of D-histidine. The major species at pH 7.3.

   
   

(2s)-2-amino-3-(1h-imidazol-2-yl)propanoic acid

(2s)-2-amino-3-(1h-imidazol-2-yl)propanoic acid

C6H9N3O2 (155.06947340000002)