Record Information
Version1.0
Creation Date2018-07-17 17:21:12 UTC
Update Date2020-04-22 15:51:41 UTC
MCDB ID BMDB0062231
Secondary Accession Numbers
  • BMDB62231
Metabolite Identification
Common NameGlutaminylhistidine
DescriptionGlutaminylhistidine, also known as Q-H dipeptide or GLN-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. Glutaminylhistidine is possibly soluble (in water) and a very strong basic compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
GLN-HisHMDB
L-Glutaminyl-L-histidineHMDB
N-GlutaminylhistidineHMDB
N-L-Glutaminyl-L-histidineHMDB
Glutaminyl-histidineHMDB
Glutamine histidine dipeptideHMDB
Glutamine-histidine dipeptideHMDB
Q-H DipeptideHMDB
QH DipeptideHMDB
L-GLN-L-HisHMDB
(2S)-2-{[(2S)-2-amino-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-3-(1H-imidazol-5-yl)propanoateHMDB
GlutaminylhistidineHMDB
Chemical FormulaC11H17N5O4
Average Molecular Weight283.288
Monoisotopic Molecular Weight283.128054047
IUPAC Name(2S)-2-{[(2S)-2-amino-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-3-(1H-imidazol-5-yl)propanoic acid
Traditional Name(2S)-2-{[(2S)-2-amino-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-3-(3H-imidazol-4-yl)propanoic acid
CAS Registry Number104018-08-8
SMILES
[H][C@](N)(CCC(O)=N)C(O)=N[C@@]([H])(CC1=CN=CN1)C(O)=O
InChI Identifier
InChI=1S/C11H17N5O4/c12-7(1-2-9(13)17)10(18)16-8(11(19)20)3-6-4-14-5-15-6/h4-5,7-8H,1-3,12H2,(H2,13,17)(H,14,15)(H,16,18)(H,19,20)/t7-,8-/m0/s1
InChI KeyJZOYFBPIEHCDFV-YUMQZZPRSA-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
  • Glutamine 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
  • N-acyl-amine
  • Fatty amide
  • Fatty acyl
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Amino acid or derivatives
  • Amino acid
  • Primary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Carboxylic acid
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Primary aliphatic amine
  • Organic oxide
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.9ALOGPS
logP-8ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)-0.66ChemAxon
pKa (Strongest Basic)12.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area168.67 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity79.43 m³·mol⁻¹ChemAxon
Polarizability27.54 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0290000000-0277566ecd2416b20aea2018-11-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gx0-7970000000-710b69e09df6a12fd2312018-11-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-e8ebc1d5476a869fa4f42018-11-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-2b9d5ca4df8f843b83622021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0540-9510000000-ed3317f2a969e022a4202021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-9000000000-1b1a277ec0dc9c18340b2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f89-0970000000-e820a1735aec7864c7232021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ke9-3910000000-e1575ca2ee5673b72f222021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-9500000000-23de5ae74ea8b6d3b43c2021-10-11View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0028799
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB098197
KNApSAcK IDNot Available
Chemspider ID7990098
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9814348
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]