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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:47:30 UTC
Update Date2020-02-26 16:25:51 UTC
HMDB IDHMDB0032055
Secondary Accession Numbers
  • HMDB32055
Metabolite Identification
Common NameN-Acetylhistidine
DescriptionN-Acetylhistidine, also known as N-alpha-L-histidine, 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. N-Acetylhistidine is a very strong basic compound (based on its pKa). N-Acetylhistidine is a constituent of the tissues of various fish and amphibian species.
Structure
Data?1573765938
Synonyms
ValueSource
N-Acetyl histidineChEBI
N-AcetylhistidineChEBI
N-alpha-L-HistidineChEBI
N-Hydroxy-aabpChEBI
N-a-L-HistidineGenerator
N-Α-L-histidineGenerator
N-Acetylhistidine, (DL)-isomerMeSH
N-Acetylhistidine monohydrateMeSH
(2S)-2-Acetamido-3-(1H-imidazol-5-yl)propanoic acidHMDB
(2S)-2-Acetamido-3-(1H-imidazol-5-yl)propionic acidHMDB
(S)-2-Acetamido-3-(1H-imidazol-4-yl)propanoicacidHMDB
N-Acetyl-L-histidineHMDB
N-alpha-Acetyl-L-histidineHMDB
N-α-Acetyl-L-histidineHMDB
N2-AcetylhistidineHMDB
Nalpha-Acetyl-L-histidineHMDB
Nalpha-AcetylhistidineHMDB
Nα-Acetyl-L-histidineHMDB
Nα-AcetylhistidineHMDB
alpha-N-Acetyl-L-histidineHMDB
α-N-Acetyl-L-histidineHMDB
Chemical FormulaC8H11N3O3
Average Molecular Weight197.194
Monoisotopic Molecular Weight197.080041226
IUPAC Name(2S)-2-acetamido-3-(1H-imidazol-4-yl)propanoic acid
Traditional Name(2S)-2-acetamido-3-(1H-imidazol-4-yl)propanoic acid
CAS Registry Number2497-02-1
SMILES
CC(=O)N[C@@H](CC1=CNC=N1)C(O)=O
InChI Identifier
InChI=1S/C8H11N3O3/c1-5(12)11-7(8(13)14)2-6-3-9-4-10-6/h3-4,7H,2H2,1H3,(H,9,10)(H,11,12)(H,13,14)/t7-/m0/s1
InChI KeyKBOJOGQFRVVWBH-ZETCQYMHSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHistidine and derivatives
Alternative Parents
Substituents
  • Histidine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Imidazolyl carboxylic acid derivative
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point187 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.09 g/LALOGPS
logP-0.34ALOGPS
logP-2.5ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)6.55ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.08 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity46.94 m³·mol⁻¹ChemAxon
Polarizability18.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008762
KNApSAcK IDNot Available
Chemspider ID68142
KEGG Compound IDC02997
BioCyc IDCPD-424
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound75619
PDB IDNot Available
ChEBI ID16437
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .