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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 21:02:50 UTC
Update Date2020-02-26 21:42:31 UTC
HMDB IDHMDB0028879
Secondary Accession Numbers
  • HMDB28879
Metabolite Identification
Common NameHistidylarginine
DescriptionHistidylarginine is a dipeptide composed of histidine and arginine. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Some dipeptides are known to have physiological or cell-signalling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.
Structure
Data?1582753351
Synonyms
ValueSource
H-R dipeptideHMDB
HR dipeptideHMDB
His-ArgHMDB
Histidine arginine dipeptideHMDB
Histidine-arginine dipeptideHMDB
Histidinyl-arginineHMDB
HistidinylarginineHMDB
Histidyl-arginineHMDB
HistidylarginineHMDB
L-His-L-ArgHMDB
L-Histidinyl-L-arginineHMDB
L-Histidyl-L-arginineHMDB
N2-HistidinylarginineHMDB
N2-HistidylarginineHMDB
N2-L-Histidinyl-L-arginineHMDB
N2-L-Histidyl-L-arginineHMDB
Chemical FormulaC12H21N7O3
Average Molecular Weight311.346
Monoisotopic Molecular Weight311.170587564
IUPAC Name(2S)-2-[(2S)-2-amino-3-(1H-imidazol-5-yl)propanamido]-5-carbamimidamidopentanoic acid
Traditional Name(2S)-2-[(2S)-2-amino-3-(3H-imidazol-4-yl)propanamido]-5-carbamimidamidopentanoic acid
CAS Registry Number77369-21-2
SMILES
N[C@@H](CC1=CN=CN1)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O
InChI Identifier
InChI=1S/C12H21N7O3/c13-8(4-7-5-16-6-18-7)10(20)19-9(11(21)22)2-1-3-17-12(14)15/h5-6,8-9H,1-4,13H2,(H,16,18)(H,19,20)(H,21,22)(H4,14,15,17)/t8-,9-/m0/s1
InChI KeyNIKBMHGRNAPJFW-IUCAKERBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • Histidine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • Fatty amide
  • Fatty acyl
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Guanidine
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Primary amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-4.45Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP-3.5ALOGPS
logP-4.4ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)12.03ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area183 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity88.78 m³·mol⁻¹ChemAxon
Polarizability31.77 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5731232
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7408563
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Prell JS, O'Brien JT, Steill JD, Oomens J, Williams ER: Structures of protonated dipeptides: the role of arginine in stabilizing salt bridges. J Am Chem Soc. 2009 Aug 19;131(32):11442-9. doi: 10.1021/ja901870d. [PubMed:19624125 ]
  2. Thorne BA, Viveros OH, Thomas G: Expression and processing of mouse proopiomelanocortin in bovine adrenal chromaffin cells. A model system to study tissue-specific prohormone processing. J Biol Chem. 1991 Jul 25;266(21):13607-15. [PubMed:1856197 ]