Np mrd loader

Showing NP-Card for Imidazolone (NP0087176)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-05-11 16:42:14 UTC
Updated at2022-05-11 16:42:14 UTC
NP-MRD IDNP0087176
Secondary Accession NumbersNone
Natural Product Identification
Common NameImidazolone
DescriptionImidazolone belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Imidazolone is a very strong basic compound (based on its pKa). In humans, imidazolone is involved in histidine metabolism. Imidazolone was first documented in 1990 (PMID: 2145908). Imidazolone is one of the major advanced glycation end (AGE) products, that accumulate in neurons in different areas of human brain tissue localized especially in human pyramidal CA4 neurons in the hippocampus in an age-dependent manner (PMID: 15899672) (PMID: 11264780) (PMID: 12406185) (PMID: 10958861).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0087176 (Imidazolone)


  Mrv0541 02231219562D          

  6  6  0  0  0  0            999 V2000
   20.8327  -11.6448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3807  -11.8747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9682  -10.6052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7932  -10.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0481  -11.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7133  -11.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  2  0  0  0  0
  4  5  1  0  0  0  0
M  END
Download

3D MOL for NP0087176 (Imidazolone)

     RDKit          3D

 10 10  0  0  0  0  0  0  0  0999 V2000
   -1.4899    1.6767   -0.0155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6438    0.7736   -0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9432   -0.6950    0.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3524   -1.3405    0.0183 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817   -0.4627   -0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7788    0.8583   -0.0201 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4992   -0.9741   -0.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4939   -0.8879    0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356   -0.6958   -0.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3215    1.7473   -0.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  2  1  0
  3  7  1  0
  3  8  1  0
  5  9  1  0
  6 10  1  0
M  END
Download

3D SDF for NP0087176 (Imidazolone)


  Mrv0541 02231219562D          

  6  6  0  0  0  0            999 V2000
   20.8327  -11.6448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3807  -11.8747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9682  -10.6052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7932  -10.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0481  -11.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7133  -11.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  2  0  0  0  0
  4  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087176

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1CN=CN1

> <INCHI_IDENTIFIER>
InChI=1S/C3H4N2O/c6-3-1-4-2-5-3/h2H,1H2,(H,4,5,6)

> <INCHI_KEY>
CAAMSDWKXXPUJR-UHFFFAOYSA-N

> <FORMULA>
C3H4N2O

> <MOLECULAR_WEIGHT>
84.0767

> <EXACT_MASS>
84.03236276

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
7.336750358876188

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5-dihydro-1H-imidazol-5-one

> <ALOGPS_LOGP>
-1.95

> <JCHEM_LOGP>
-1.1527121286666664

> <ALOGPS_LOGS>
-0.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.31757351588761

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.394171039548826

> <JCHEM_PKA_STRONGEST_BASIC>
5.1212465449545

> <JCHEM_POLAR_SURFACE_AREA>
41.46

> <JCHEM_REFRACTIVITY>
19.936

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
imidazol-4-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0087176 (Imidazolone)

Download
PDB for NP0087176 (Imidazolone)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      38.888 -21.737   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      36.177 -22.166   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      35.407 -19.796   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      36.947 -19.796   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      37.423 -21.261   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      34.931 -21.261   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    5    6                                                       
CONECT    3    4    6                                                       
CONECT    4    3    5                                                       
CONECT    5    1    2    4                                                  
CONECT    6    2    3                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   12    0
END

Download
3D PDB for NP0087176 (Imidazolone)
Download
SMILES for NP0087176 (Imidazolone)
O=C1CN=CN1
Download
INCHI for NP0087176 (Imidazolone)
InChI=1S/C3H4N2O/c6-3-1-4-2-5-3/h2H,1H2,(H,4,5,6)
Download
View in JSmol
Synonyms
ValueSource
4-ImidazoloneChEBI
Imidazol-4-oneChEBI
1-Imidazolin-5-oneHMDB
1H-Imidazol-5(4H)-oneHMDB
2-Imidazolin-4-oneHMDB
2-Imidazolin-5-oneHMDB
3,5-Dihydro-4H-imidazol-4-oneHMDB
ImidazoloneChEBI
Chemical FormulaC3H4N2O
Average Mass84.0767 Da
Monoisotopic Mass84.03236 Da
IUPAC Name4,5-dihydro-1H-imidazol-5-one
Traditional Nameimidazol-4-one
CAS Registry NumberNot Available
SMILES
O=C1CN=CN1
InChI Identifier
InChI=1S/C3H4N2O/c6-3-1-4-2-5-3/h2H,1H2,(H,4,5,6)
InChI KeyCAAMSDWKXXPUJR-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 Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlpha amino acids and derivatives  
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
    • 

  • Imidazolinone
    • 

  • 2-imidazoline
    • 

  • Amidine
    • 

  • Carboxylic acid amidine
    • 

  • Carboximidamide
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Organic 1,3-dipolar compound
    • 

  • Organoheterocyclic compound
    • 

  • Azacycle
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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-2ALOGPS
logP-1.2ChemAxon
logS-0.06ALOGPS
pKa (Strongest Acidic)13.39ChemAxon
pKa (Strongest Basic)5.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity19.94 m³·mol⁻¹ChemAxon
Polarizability7.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004363  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023367  
KNApSAcK IDNot Available
Chemspider ID490  
KEGG Compound IDC06195  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkImidazoline  
METLIN ID7054  
PubChem Compound504  
PDB IDNot Available
ChEBI ID28470  
Good Scents IDNot Available
References
General References
  1. Zhang X, Frischmann M, Kientsch-Engel R, Steinmann K, Stopper H, Niwa T, Pischetsrieder M: Two immunochemical assays to measure advanced glycation end-products in serum from dialysis patients. Clin Chem Lab Med. 2005;43(5):503-11. doi: 10.1515/CCLM.2005.089. [PubMed:15899672  ] 
  2. Ings RM, Gray AJ, Taylor AR, Gordon BH, Breen M, Hiley M, Brownsill R, Marchant N, Richards R, Wallace D, et al.: Disposition, pharmacokinetics, and metabolism of 14C-fotemustine in cancer patients. Eur J Cancer. 1990;26(7):838-42. doi: 10.1016/0277-5379(90)90166-q. [PubMed:2145908  ] 
  3. Niwa T: Dialysis-related amyloidosis: pathogenesis focusing on AGE modification. Semin Dial. 2001 Mar-Apr;14(2):123-6. doi: 10.1046/j.1525-139x.2001.00031.x. [PubMed:11264780  ] 
  4. Jono T, Kimura T, Takamatsu J, Nagai R, Miyazaki K, Yuzuriha T, Kitamura T, Horiuchi S: Accumulation of imidazolone, pentosidine and N(epsilon)-(carboxymethyl)lysine in hippocampal CA4 pyramidal neurons of aged human brain. Pathol Int. 2002 Sep;52(9):563-71. doi: 10.1046/j.1320-5463.2002.01390.x. [PubMed:12406185  ] 
  5. Franke S, Niwa T, Deuther-Conrad W, Sommer M, Hein G, Stein G: Immunochemical detection of imidazolone in uremia and rheumatoid arthritis. Clin Chim Acta. 2000 Oct;300(1-2):29-41. doi: 10.1016/s0009-8981(00)00299-0. [PubMed:10958861  ]