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Showing NP-Card for 1H-Imidazole-4(5)-propanoic acid (NP0086521)

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Record Information
Version2.0
Created at2022-05-11 16:23:11 UTC
Updated at2022-05-11 16:23:11 UTC
NP-MRD IDNP0086521
Secondary Accession NumbersNone
Natural Product Identification
Common Name1H-Imidazole-4(5)-propanoic acid
DescriptionImidazolepropionic acid, also known as deaminohistidine or 4-imidazolylpropionate, 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. Imidazolepropionic acid is a very strong basic compound (based on its pKa). Imidazolepropionic acid exists in all living organisms, ranging from bacteria to humans. 1H-Imidazole-4(5)-propanoic acid is found in Coprinopsis atramentaria. 1H-Imidazole-4(5)-propanoic acid was first documented in 1962 (PMID: 13987921). A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 3 has been replaced by an imidazol-4-yl group (PMID: 6136484) (PMID: 23078170) (PMID: 2547218).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086521 (1H-Imidazole-4(5)-propanoic acid)


  Mrv1652311041919122D          

 10 10  0  0  0  0            999 V2000
 9999.978410000.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6931 9999.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.409210000.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1253 9999.7576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.409210000.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.590710000.2517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9233 9999.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1782 9998.9821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0032 9998.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2581 9999.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  9 10  2  0  0  0  0
  6  7  2  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1 10  1  0  0  0  0
M  END
Download

3D MOL for NP0086521 (1H-Imidazole-4(5)-propanoic acid)

     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
    2.8290   -1.4530    1.0656 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6099   -0.2559    0.7712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7078    0.5215    0.4546 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2073    0.2171    0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771   -0.2631   -0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8568    0.1892   -0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9606   -0.4815   -0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0456    0.2809   -0.3378 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6549    1.4158   -0.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164    1.3469   -1.0700 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6144    0.3890    0.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036   -0.2623    1.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1444    1.3201    0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1548    0.1558   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5689   -1.3689   -0.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230   -1.4503    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0531    0.0589   -0.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3068    2.2413   -1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
M  END
Download

3D SDF for NP0086521 (1H-Imidazole-4(5)-propanoic acid)


  Mrv1652311041919122D          

 10 10  0  0  0  0            999 V2000
 9999.978410000.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6931 9999.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.409210000.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1253 9999.7576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.409210000.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.590710000.2517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9233 9999.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1782 9998.9821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0032 9998.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2581 9999.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  9 10  2  0  0  0  0
  6  7  2  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086521

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CCC1=CNC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C6H8N2O2/c9-6(10)2-1-5-3-7-4-8-5/h3-4H,1-2H2,(H,7,8)(H,9,10)

> <INCHI_KEY>
ZCKYOWGFRHAZIQ-UHFFFAOYSA-N

> <FORMULA>
C6H8N2O2

> <MOLECULAR_WEIGHT>
140.1399

> <EXACT_MASS>
140.05857751

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
13.59353142060863

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(1H-imidazol-5-yl)propanoic acid

> <ALOGPS_LOGP>
-0.09

> <JCHEM_LOGP>
-1.0927005043754943

> <ALOGPS_LOGS>
-0.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.975907586137506

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.035312219151665

> <JCHEM_PKA_STRONGEST_BASIC>
6.7653984265305445

> <JCHEM_POLAR_SURFACE_AREA>
65.98

> <JCHEM_REFRACTIVITY>
34.9529

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.59e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-imidazolepropionic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0086521 (1H-Imidazole-4(5)-propanoic acid)

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PDB for NP0086521 (1H-Imidazole-4(5)-propanoic acid)
HEADER    PROTEIN                                 04-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-NOV-19         0                                  
HETATM    1  C   UNK     0    8666.6268666.983   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.9608666.214   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8669.2978666.983   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8670.6348666.214   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8669.2978668.524   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0    8664.0368667.137   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0    8662.7908666.231   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0    8663.2668664.767   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0    8664.8068664.767   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.2828666.231   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    7   10                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9   10    8                                                       
CONECT   10    9    6    1                                                  
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0086521 (1H-Imidazole-4(5)-propanoic acid)
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SMILES for NP0086521 (1H-Imidazole-4(5)-propanoic acid)
OC(=O)CCC1=CNC=N1
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INCHI for NP0086521 (1H-Imidazole-4(5)-propanoic acid)
InChI=1S/C6H8N2O2/c9-6(10)2-1-5-3-7-4-8-5/h3-4H,1-2H2,(H,7,8)(H,9,10)
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View in JSmol
Synonyms
ValueSource
1H-Imidazole-4-propanoic acidChEBI
3-(1H-Imidazol-4-yl)propionic acidChEBI
3-(Imidazol-4-yl)propanoic acidChEBI
3-(Imidazol-4-yl)propionic acidChEBI
4-Imidazolylpropanoic acidChEBI
4-Imidazolylpropionic acidChEBI
DeaminohistidineChEBI
Imidazolylpropionic acidChEBI
3-(1H-Imidazol-4-yl)propanoateKegg
1H-Imidazole-4-propanoateGenerator
3-(1H-Imidazol-4-yl)propionateGenerator
3-(Imidazol-4-yl)propanoateGenerator
3-(Imidazol-4-yl)propionateGenerator
4-ImidazolylpropanoateGenerator
4-ImidazolylpropionateGenerator
ImidazolylpropionateGenerator
3-(1H-Imidazol-4-yl)propanoic acidGenerator
ImidazolepropionateGenerator
DihydrourocanateHMDB
3-(1H-Imidazol-4-yl)-propionateHMDB
3-(1H-Imidazol-4-yl)-propionic acidHMDB
5-ImidazolepropionateHMDB
5-Imidazolepropionic acidHMDB
Deamino-histidineHMDB
UROHMDB
Imidazole propionateHMDB
1H-Imidazole-4(5)-propanoateHMDB
1H-Imidazole-4-propionic acidHMDB
3-(1H-4-Imidazolyl)propanoic acidHMDB
3-(1H-4-Imidazolyl)propionic acidHMDB
3-(4-Imidazolyl)propanoic acidHMDB
3-(4-Imidazolyl)propionic acidHMDB
3-(Imidazol-4(5)-yl)propanoic acidHMDB
3-(Imidazol-4(5)-yl)propionic acidHMDB
5-(2-Carboxyethyl) imidazoleHMDB
Dihydrourocanic acidHMDB
Dihydrourocanoic acidHMDB
Imidazole-4(5)-propanoic acidHMDB
Imidazole-4(5)-propionic acidHMDB
Imidazole-4-propanoic acidHMDB
Imidazole-4-propionic acidHMDB
Imidazolylpropanoic acidHMDB
beta-(5-Imidazolyl)propanoic acidHMDB
beta-(5-Imidazolyl)propionic acidHMDB
beta-Imidazolyl-4(5)-propanoic acidHMDB
beta-Imidazolyl-4(5)-propionic acidHMDB
Β-(5-imidazolyl)propanoic acidHMDB
Β-(5-imidazolyl)propionic acidHMDB
Β-imidazolyl-4(5)-propanoic acidHMDB
Β-imidazolyl-4(5)-propionic acidHMDB
Chemical FormulaC6H8N2O2
Average Mass140.1399 Da
Monoisotopic Mass140.05858 Da
IUPAC Name3-(1H-imidazol-5-yl)propanoic acid
Traditional Name5-imidazolepropionic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CCC1=CNC=N1
InChI Identifier
InChI=1S/C6H8N2O2/c9-6(10)2-1-5-3-7-4-8-5/h3-4H,1-2H2,(H,7,8)(H,9,10)
InChI KeyZCKYOWGFRHAZIQ-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
Coprinopsis atramentariaLOTUS Database
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 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
    • 

  • Heteroaromatic compound
    • 

  • Azacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • 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-0.09ALOGPS
logP-1.1ChemAxon
logS-0.48ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)6.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.98 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.95 m³·mol⁻¹ChemAxon
Polarizability13.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002271  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012461  
KNApSAcK IDNot Available
Chemspider ID63798  
KEGG Compound IDC20522  
BioCyc IDCPD-15171  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6585  
PubChem Compound70630  
PDB IDNot Available
ChEBI ID73087  
Good Scents IDNot Available
References
General References
  1. Antener I, Verwilghen AM, Van Geert C, Mauron J: Biochemical study of malnutrition. Part VI: Histidine and its metabolites. Int J Vitam Nutr Res. 1983;53(2):199-209. [PubMed:6136484  ] 
  2. SEN NP, McGEER PL, PAUL RM: Imidazolepropionic acid as a urinary metabolite of L-histidine. Biochem Biophys Res Commun. 1962 Oct 17;9:257-61. doi: 10.1016/0006-291x(62)90069-4. [PubMed:13987921  ] 
  3. Bogachev AV, Bertsova YV, Bloch DA, Verkhovsky MI: Urocanate reductase: identification of a novel anaerobic respiratory pathway in Shewanella oneidensis MR-1. Mol Microbiol. 2012 Dec;86(6):1452-63. doi: 10.1111/mmi.12067. Epub 2012 Nov 1. [PubMed:23078170  ] 
  4. Norval M, Simpson TJ, Bardshiri E, Howie SE: Urocanic acid analogues and the suppression of the delayed type hypersensitivity response to Herpes simplex virus. Photochem Photobiol. 1989 May;49(5):633-9. doi: 10.1111/j.1751-1097.1989.tb08435.x. [PubMed:2547218  ]