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Record Information
Version1.0
Created at2022-05-12 15:13:20 UTC
Updated at2022-05-12 15:13:20 UTC
NP-MRD IDNP0136391
Secondary Accession NumbersNone
Natural Product Identification
Common NameAspartyl-Histidine
DescriptionAspartyl-Histidine, also known as D-H dipeptide or asp-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. Aspartyl-Histidine is a very strong basic compound (based on its pKa). Aspartyl-Histidine is a dipeptide composed of aspartate and histidine. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite. It is an incomplete breakdown product of protein digestion or protein catabolism. It was first documented in 1993 (PMID: 7902418). Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.
Structure
Thumb
Synonyms
ValueSource
Asp-hisHMDB
Aspartate histidine dipeptideHMDB
Aspartate-histidine dipeptideHMDB
AspartylhistidineHMDB
D-H DipeptideHMDB
DH DipeptideHMDB
L-Aspartyl-L-histidineHMDB
3-Amino-3-{[1-carboxy-2-(1H-imidazol-5-yl)ethyl]-C-hydroxycarbonimidoyl}propanoateGenerator
Chemical FormulaC10H14N4O5
Average Mass270.2420 Da
Monoisotopic Mass270.09642 Da
IUPAC Name3-amino-3-{[1-carboxy-2-(1H-imidazol-5-yl)ethyl]carbamoyl}propanoic acid
Traditional Name3-amino-3-{[1-carboxy-2-(3H-imidazol-4-yl)ethyl]carbamoyl}propanoic acid
CAS Registry NumberNot Available
SMILES
NC(CC(O)=O)C(=O)NC(CC1=CN=CN1)C(O)=O
InChI Identifier
InChI=1S/C10H14N4O5/c11-6(2-8(15)16)9(17)14-7(10(18)19)1-5-3-12-4-13-5/h3-4,6-7H,1-2,11H2,(H,12,13)(H,14,17)(H,15,16)(H,18,19)
InChI KeyHSPSXROIMXIJQW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
  • Aspartic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • N-acyl-amine
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Organoheterocyclic compound
  • Carboxylic acid
  • Azacycle
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen 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-3.2ALOGPS
logP-6.8ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.86ChemAxon
pKa (Strongest Basic)8.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area158.4 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity61.39 m³·mol⁻¹ChemAxon
Polarizability25.19 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0028755
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 Compound14717808
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Sovago I, Farkas E, Bertalan C, Lebkiri A, Kowalik-Jankowska T, Kozlowski H: Copper(II) complexes of dipeptides containing aspartyl, glutamyl, and histidyl residues in the side chain. J Inorg Biochem. 1993 Sep;51(4):715-26. doi: 10.1016/0162-0134(93)85004-r. [PubMed:7902418 ]