N-Acetylhistidine

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

Formula: C8H11N3O3 (197.08)
Chinese Name: N-乙酰-L-组氨酸, N-乙酰基-L-组氨酸
BioDeep ID: BioDeep_00000003001 ( View LC/MS Profile)
SMILES: CC(=O)N[C@@H](CC1=CNC=N1)C(O)=O



Found 15 Sample Hits

m/z Adducts Species Organ Scanning Sample
162.0677 [M+H-2H2O]+
PPM:9.4
Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

162.0668 [M+H-2H2O]+
PPM:3.8
Homo sapiens esophagus DESI ()
LNTO22_1_4 - MTBLS385
Resolution: 17μm, 82x80

Description

198.0878 [M+H]+
PPM:2.5
Homo sapiens esophagus DESI ()
LNTO22_1_4 - MTBLS385
Resolution: 17μm, 82x80

Description

162.0683 [M+H-2H2O]+
PPM:13.1
Homo sapiens esophagus DESI ()
LNTO22_1_9 - MTBLS385
Resolution: 75μm, 89x74

Description

198.088 [M+H]+
PPM:3.5
Homo sapiens esophagus DESI ()
TO31T - MTBLS385
Resolution: 75μm, 56x54

Description

198.0883 [M+H]+
PPM:5
Homo sapiens esophagus DESI ()
TO29T - MTBLS385
Resolution: 75μm, 56x48

Description

198.0912 [M+H]+
PPM:19.6
Homo sapiens esophagus DESI ()
LNTO22_1_5 - MTBLS385
Resolution: 75μm, 135x94

Description

162.0679 [M+H-2H2O]+
PPM:10.6
Homo sapiens esophagus DESI ()
LNTO22_1_8 - MTBLS385
Resolution: 75μm, 69x61

Description

162.0677 [M+H-2H2O]+
PPM:9.4
Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

198.0889 [M+H]+
PPM:8
Mus musculus brain MALDI (DHB)
Brain01_Bregma-3-88b_centroid - MTBLS313
Resolution: 17μm, 265x320

Description

198.089 [M+H]+
PPM:8.5
Mus musculus brain MALDI (DHB)
Brain01_Bregma1-42_02_centroid - MTBLS313
Resolution: 17μm, 434x258

Description

198.0891 [M+H]+
PPM:9
Mus musculus brain MALDI (DHB)
Brain01_Bregma1-42_01_centroid - MTBLS313
Resolution: 17μm, 447x118

Description

198.0885 [M+H]+
PPM:6
Mus musculus brain MALDI (DHB)
Brain02_Bregma1-42_03 - MTBLS313
Resolution: 17μm, 483x403

Description

198.0885 [M+H]+
PPM:6
Mus musculus brain MALDI (DHB)
Brain02_Bregma-3-88 - MTBLS313
Resolution: 17μm, 288x282

Description

198.0885 [M+H]+
PPM:6
Mus musculus brain MALDI (DHB)
Brain02_Bregma-1-46 - MTBLS313
Resolution: 17μm, 294x399

Description


N-Acetyl-L-histidine or N-Acetylhistidine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetylhistidine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylhistidine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-histidine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618). About 85\\% of all human proteins and 68\\% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylhistidine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free histidine can also occur. In particular, N-Acetylhistidine can be biosynthesized from L-histidine and acetyl-CoA by the enzyme histidine N-acetyltransferase (EC 2.3.1.33). Many N-acetylamino acids are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986; PMID: 20613759). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557). Constituent of the tissues of various fish and amphibian subspecies N-Acetylhistidine is found in fishes. KEIO_ID A073