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Record Information
Version2.0
Created at2022-09-12 16:45:01 UTC
Updated at2022-09-12 16:45:01 UTC
NP-MRD IDNP0330926
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-[(3-amino-1-hydroxypropylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid
DescriptionPhosphoglucomutase belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. Phosphoglucomutase is a very strong basic compound (based on its pKa). In humans, phosphoglucomutase is involved in the metabolic disorder called the sucrase-isomaltase deficiency pathway. This glucose 1-phosphate molecule is not itself a useful metabolic intermediate, but phosphoglucomutase catalyzes the conversion of this glucose 1-phosphate to glucose 6-phosphate (see below for the mechanism of this reaction). Outside of the human body, Phosphoglucomutase has been detected, but not quantified in, soy beans. This could make phosphoglucomutase a potential biomarker for the consumption of these foods. Substrate-velocity relationships and induced transport tests have revealed that the dephosphorylated enzyme then facilitates the transfer of a phosphoryl group from the glucose-1,6-bisphosphate intermediate to the enzyme, regenerating phosphorylated phosphoglucomutase and yielding glucose 6-phosphate (in the forward direction). The burial of the active site (including Ser-116, the critical residue on the enzyme that is phosphorylated and dephosphorylated) in the hydrophobic interior of the enzyme serves to exclude water from counterproductively hydrolyzing critical phosphoester bonds while still allowing the substrate to access the active site. If glycogenolysis is taking place in the liver, glucose 6-phosphate can be converted to glucose by the enzyme glucose 6-phosphatase; the glucose produced in the liver is then released to the bloodstream for use in other organs. Human muscle contains two phosphoglucomutases with nearly identical catalytic properties, PGM I and PGM II. 2-[(3-amino-1-hydroxypropylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid is found in Daphnia magna, Homo sapiens and Mus musculus. PGM deficiency is an extremely rare condition that does not have a set of well-characterized physiological symptoms.
Structure
Thumb
Synonyms
ValueSource
Ribonuclease, pancreaticMeSH
RNase aMeSH
Ribonuclease IMeSH
Ribonuclease aMeSH
Ribonuclease (pancreatic)MeSH
RNase IMeSH
Pancreatic rnaseMeSH
Pancreatic ribonucleaseMeSH
RNase, pancreaticMeSH
Chemical FormulaC9H14N4O3
Average Mass226.2325 Da
Monoisotopic Mass226.10659 Da
IUPAC Name2-[(3-amino-1-hydroxypropylidene)amino]-3-(1H-imidazol-5-yl)propanoic acid
Traditional Name2-[(3-amino-1-hydroxypropylidene)amino]-3-(3H-imidazol-4-yl)propanoic acid
CAS Registry NumberNot Available
SMILES
NCCC(O)=NC(CC1=CN=CN1)C(O)=O
InChI Identifier
InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)
InChI KeyCQOVPNPJLQNMDC-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Daphnia magnaLOTUS Database
Homo sapiensLOTUS Database
Mus musculusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassHybrid peptides
Direct ParentHybrid peptides
Alternative Parents
Substituents
  • Hybrid peptide
  • Histidine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Beta amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Organoheterocyclic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Primary amine
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Amine
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen 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-3ALOGPS
logP-4.9ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.42ChemAxon
pKa (Strongest Basic)10.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.59 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity56.08 m³·mol⁻¹ChemAxon
Polarizability22.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005612
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhosphoglucomutase
METLIN IDNot Available
PubChem Compound9369
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]