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Showing NP-Card for Pi-Methylimidazoleacetic acid (NP0087338)

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Record Information
Version1.0
Created at2022-05-11 16:46:56 UTC
Updated at2022-05-11 16:46:56 UTC
NP-MRD IDNP0087338
Secondary Accession NumbersNone
Natural Product Identification
Common NamePi-Methylimidazoleacetic acid
DescriptionPi-Methylimidazoleacetic acid, also known as 1-methyl-imidazole-5-acetate or p-miaa, belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring. Pi-Methylimidazoleacetic acid is found in Trypanosoma brucei. It was first documented in 1981 (PMID: 7462662). Pi-Methylimidazoleacetic acid is a very strong basic compound (based on its pKa) (PMID: 3597642) (PMID: 7130180) (PMID: 7934197) (PMID: 7711000).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0087338 (Pi-Methylimidazoleacetic acid)


  Mrv0541 02231220192D          

 10 10  0  0  0  0            999 V2000
   15.4375  -10.7954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4365  -11.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2217  -11.8745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7061  -11.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2212  -10.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5311  -11.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9437  -10.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7686  -10.4923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5311   -9.7777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4770  -12.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  1  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  3 10  1  0  0  0  0
M  END
Download

3D MOL for NP0087338 (Pi-Methylimidazoleacetic acid)

     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -1.4545   -1.1390    0.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2705    0.1062    0.1518 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1313    1.1013   -0.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5702    2.0542   -0.7849 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3309    1.6708   -1.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1618    0.4278   -0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636   -0.4084   -0.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0107   -0.1277    0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7636    0.7370    1.3596 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036   -0.8231    0.5723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0145   -1.9426    0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5340   -1.3536    1.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9126   -1.0503    1.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1346    1.1731    0.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3724    2.2240   -1.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032   -1.5039   -0.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4857   -0.2598   -1.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8121   -0.8859   -0.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  6  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  5 15  1  0
  7 16  1  0
  7 17  1  0
 10 18  1  0
M  END
Download

3D SDF for NP0087338 (Pi-Methylimidazoleacetic acid)


  Mrv0541 02231220192D          

 10 10  0  0  0  0            999 V2000
   15.4375  -10.7954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4365  -11.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2217  -11.8745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7061  -11.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2212  -10.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5311  -11.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9437  -10.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7686  -10.4923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5311   -9.7777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4770  -12.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  1  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  3 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087338

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=NC=C1CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8N2O2/c1-8-4-7-3-5(8)2-6(9)10/h3-4H,2H2,1H3,(H,9,10)

> <INCHI_KEY>
UJCGYTCAMOHYCG-UHFFFAOYSA-N

> <FORMULA>
C6H8N2O2

> <MOLECULAR_WEIGHT>
140.1399

> <EXACT_MASS>
140.05857751

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
13.379092552536367

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(1-methyl-1H-imidazol-5-yl)acetic acid

> <ALOGPS_LOGP>
-0.39

> <JCHEM_LOGP>
-1.1706128810808187

> <ALOGPS_LOGS>
-1.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.813742797499522

> <JCHEM_PKA_STRONGEST_BASIC>
6.6276245024028

> <JCHEM_POLAR_SURFACE_AREA>
55.12

> <JCHEM_REFRACTIVITY>
35.0946

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
P-miaa

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0087338 (Pi-Methylimidazoleacetic acid)

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PDB for NP0087338 (Pi-Methylimidazoleacetic acid)
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  N   UNK     0      28.817 -20.151   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      28.815 -21.690   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      30.280 -22.166   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      31.185 -20.919   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.280 -19.674   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.725 -20.919   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.495 -19.586   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      35.035 -19.586   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      32.725 -18.252   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      30.757 -23.630   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0087338 (Pi-Methylimidazoleacetic acid)
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SMILES for NP0087338 (Pi-Methylimidazoleacetic acid)
CN1C=NC=C1CC(O)=O
Download
INCHI for NP0087338 (Pi-Methylimidazoleacetic acid)
InChI=1S/C6H8N2O2/c1-8-4-7-3-5(8)2-6(9)10/h3-4H,2H2,1H3,(H,9,10)
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Synonyms
ValueSource
1-Methyl-imidazole-5-acetic acidChEBI
pros-Methylimidazoleacetic acidChEBI
1-Methyl-imidazole-5-acetateGenerator
pros-MethylimidazoleacetateGenerator
Pi-methylimidazoleacetateGenerator
1-Methyl-5-imidazoleacetateHMDB
p-MIAAHMDB
1-Methyl-5-imidazoleacetic acidHMDB
Pi-methylimidazoleacetic acidChEBI
Chemical FormulaC6H8N2O2
Average Mass140.1399 Da
Monoisotopic Mass140.05858 Da
IUPAC Name2-(1-methyl-1H-imidazol-5-yl)acetic acid
Traditional NameP-miaa
CAS Registry NumberNot Available
SMILES
CN1C=NC=C1CC(O)=O
InChI Identifier
InChI=1S/C6H8N2O2/c1-8-4-7-3-5(8)2-6(9)10/h3-4H,2H2,1H3,(H,9,10)
InChI KeyUJCGYTCAMOHYCG-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
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassAzoles  
Sub ClassImidazoles  
Direct ParentImidazolyl carboxylic acids and derivatives  
Alternative Parents
Substituents
  • Imidazolyl carboxylic acid derivative
    • 

  • N-substituted imidazole
    • 

  • Heteroaromatic compound
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Azacycle
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic 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-0.39ALOGPS
logP-1.2ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.81ChemAxon
pKa (Strongest Basic)6.63ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.12 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity35.09 m³·mol⁻¹ChemAxon
Polarizability13.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004988  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023572  
KNApSAcK IDNot Available
Chemspider ID4954265  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7239  
PubChem Compound6451814  
PDB IDNot Available
ChEBI ID70966  
Good Scents IDNot Available
References
General References
  1. Tsuruta Y, Tomida H, Kohashi K, Ohkura Y: Simultaneous determination of imidazoleacetic acid and N tau- and N pi-methylimidazoleacetic acids in human urine by high-performance liquid chromatography with fluorescence detection. J Chromatogr. 1987 Apr 24;416(1):63-9. [PubMed:3597642  ] 
  2. Khandelwal JK, Hough LB, Pazhenchevsky B, Morrishow AM, Green JP: Presence and measurement of methylimidazoleacetic acids in brain and body fluids. J Biol Chem. 1982 Nov 10;257(21):12815-9. [PubMed:7130180  ] 
  3. Yocum MW, Butterfield JH, Gharib H: Increased plasma calcitonin levels in systemic mast cell disease. Mayo Clin Proc. 1994 Oct;69(10):987-90. [PubMed:7934197  ] 
  4. Prell GD, Green JP, Kaufmann CA, Khandelwal JK, Morrishow AM, Kirch DG, Linnoila M, Wyatt RJ: Histamine metabolites in cerebrospinal fluid of patients with chronic schizophrenia: their relationships to levels of other aminergic transmitters and ratings of symptoms. Schizophr Res. 1995 Jan;14(2):93-104. [PubMed:7711000  ] 
  5. Granerus G, Roupe G, Swanbeck G: Decreased urinary histamine metabolite after successful PUVA treatment of urticaria pigmentosa. J Invest Dermatol. 1981 Jan;76(1):1-3. [PubMed:7462662  ]