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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 21:03:28 UTC
Update Date2020-02-26 21:42:48 UTC
HMDB IDHMDB0029041
Secondary Accession Numbers
  • HMDB29041
Metabolite Identification
Common NameSerylhistidine
DescriptionSerylhistidine, also known as S-H or L-ser-L-his, 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. Serylhistidine is a very strong basic compound (based on its pKa). It is an incomplete breakdown product of protein digestion or protein catabolism.
Structure
Data?1582753368
Synonyms
ValueSource
L-Ser-L-hisChEBI
S-HChEBI
SHChEBI
L-Seryl-L-histidineHMDB
N-L-Seryl-L-histidineHMDB
N-SerylhistidineHMDB
S-H DipeptideHMDB
SH DipeptideHMDB
Ser-hisHMDB
Serine histidine dipeptideHMDB
Serine-histidine dipeptideHMDB
Serinyl-histidineHMDB
SerinylhistidineHMDB
Seryl-histidineHMDB
SerylhistidineChEBI
Chemical FormulaC9H14N4O4
Average Molecular Weight242.235
Monoisotopic Molecular Weight242.101504947
IUPAC Name(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-(1H-imidazol-4-yl)propanoic acid
Traditional Name(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-(1H-imidazol-4-yl)propanoic acid
CAS Registry Number67726-09-4
SMILES
N[C@@H](CO)C(=O)N[C@@H](CC1=CNC=N1)C(O)=O
InChI Identifier
InChI=1S/C9H14N4O4/c10-6(3-14)8(15)13-7(9(16)17)1-5-2-11-4-12-5/h2,4,6-7,14H,1,3,10H2,(H,11,12)(H,13,15)(H,16,17)/t6-,7-/m0/s1
InChI KeyYZMPDHTZJJCGEI-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
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Serine or derivatives
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid salt
  • Amino acid
  • Secondary carboxylic acid amide
  • Organoheterocyclic compound
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Primary alcohol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Primary amine
  • Alcohol
  • Organic zwitterion
  • Organic salt
  • 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-4.97Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility13.9 g/LALOGPS
logP-3ALOGPS
logP-4.9ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)7.87ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area141.33 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity56.33 m³·mol⁻¹ChemAxon
Polarizability22.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fu-7290000000-46e81e2ff3294de15b28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9520000000-ae57542e6d7eebde5eb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9200000000-67340db0c0792d530b0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0390000000-73353b9032d582c33cf7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ir3-5940000000-f4983d6b11762d60e0e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-d9d7da4dbaed23511029Spectrum
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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7016093
PDB IDNot Available
ChEBI ID73651
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Schmiedl A, Breitling F, Winter CH, Queitsch I, Dubel S: Effects of unpaired cysteines on yield, solubility and activity of different recombinant antibody constructs expressed in E. coli. J Immunol Methods. 2000 Aug 28;242(1-2):101-14. [PubMed:10986393 ]