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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 21:02:54 UTC
Update Date2020-02-26 21:42:32 UTC
HMDB IDHMDB0028894
Secondary Accession Numbers
  • HMDB28894
Metabolite Identification
Common NameHistidylserine
DescriptionHistidylserine is a dipeptide composed of histidine and serine. 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?1582753352
Synonyms
ValueSource
Histidinyl-serineChEBI
HistidylserineChEBI
HSChEBI
L-His-L-serChEBI
H-S dipeptideHMDB
HS dipeptideHMDB
His-SerHMDB
Histidine serine dipeptideHMDB
Histidine-serine dipeptideHMDB
HistidinylserineHMDB
Histidyl-serineHMDB
L-Histidinyl-L-serineHMDB
L-Histidyl-L-serineHMDB
N-HistidinylserineHMDB
N-HistidylserineHMDB
N-L-Histidinyl-L-serineHMDB
N-L-Histidyl-L-serineHMDB
Chemical FormulaC9H14N4O4
Average Molecular Weight242.235
Monoisotopic Molecular Weight242.101504947
IUPAC Name(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-hydroxypropanoic acid
Traditional Name(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-hydroxypropanoic acid
CAS Registry Number21438-60-8
SMILES
N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CO)C(O)=O
InChI Identifier
InChI=1S/C9H14N4O4/c10-6(1-5-2-11-4-12-5)8(15)13-7(3-14)9(16)17/h2,4,6-7,14H,1,3,10H2,(H,11,12)(H,13,15)(H,16,17)/t6-,7-/m0/s1
InChI KeyKRBMQYPTDYSENE-BQBZGAKWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Histidine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Serine or derivatives
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Beta-hydroxy acid
  • Aralkylamine
  • Fatty amide
  • Hydroxy acid
  • Fatty acyl
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid salt
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Alcohol
  • Primary aliphatic amine
  • Organic salt
  • Hydrocarbon derivative
  • Amine
  • Organic zwitterion
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Primary amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-4.92Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility13.6 g/LALOGPS
logP-3ALOGPS
logP-4.8ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.23ChemAxon
pKa (Strongest Basic)7.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area141.33 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity56.33 m³·mol⁻¹ChemAxon
Polarizability23.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
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 ID5360951
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6992829
PDB IDNot Available
ChEBI ID74056
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Reddy PR, Manjula P: Mixed-ligand copper(II)-phenanthroline-dipeptide complexes: synthesis, characterization, and DNA-cleavage properties. Chem Biodivers. 2007 Mar;4(3):468-80. [PubMed:17372949 ]
  2. Reddy PR, Mohan SK, Rao KS: Ternary zinc(II)-dipeptide complexes for the hydrolytic cleavage of DNA at physiological pH. Chem Biodivers. 2005 May;2(5):672-83. [PubMed:17192010 ]
  3. Ho PH, Stroobants K, Parac-Vogt TN: Hydrolysis of serine-containing peptides at neutral pH promoted by [MoO4]2- oxyanion. Inorg Chem. 2011 Dec 5;50(23):12025-33. doi: 10.1021/ic2015034. Epub 2011 Oct 31. [PubMed:22040112 ]