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Showing NP-Card for Imidazoleacetic acid (NP0000427)

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Record Information
Version1.0
Created at2006-05-22 14:17:32 UTC
Updated at2024-04-19 09:28:04 UTC
NP-MRD IDNP0000427
Secondary Accession NumbersNone
Natural Product Identification
Common NameImidazoleacetic acid
DescriptionImidazol-4-ylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by an imidazol-4-yl group. It has a role as a mouse metabolite. It is a monocarboxylic acid and a member of imidazoles. It derives from an acetic acid. It is a conjugate acid of an imidazol-4-ylacetate. It is a tautomer of an imidazol-5-ylacetic acid and a 2H-imidazol-4-ylacetic acid. Imidazoleacetic acid, also known as 4(5)-imidazoleacetate or IAA, 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. Imidazoleacetic acid exists in all living organisms, ranging from bacteria to humans. Imidazoleacetic acid can be biosynthesized from imidazole-4-acetaldehyde through its interaction with the enzyme aldehyde dehydrogenase, mitochondrial. In humans, imidazoleacetic acid is involved in histidine metabolism. Outside of the human body, Imidazoleacetic acid has been detected, but not quantified in several different foods, such as chinese cinnamons, jostaberries, vanilla, butternut squash, and red rices. Imidazoleacetic acid is a potentially toxic compound. Imidazoleacetic acid is a metabolite product of Histamine metabolism.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000427 (Imidazoleacetic acid)


  Mrv1652305271900162D          

  9  9  0  0  0  0            999 V2000
   19.3428   -4.0814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3866   -3.0196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4930   -4.6085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0805   -3.3391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1604   -4.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9451   -4.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9055   -3.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8255   -4.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5581   -3.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  3  5  1  0  0  0  0
  3  8  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  9  1  0  0  0  0
M  END
Download

3D MOL for NP0000427 (Imidazoleacetic acid)

HMDB0002024
     RDKit          3D
Imidazoleacetic acid
 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.1351    0.7461   -1.4990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9127    0.0057   -0.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810   -1.2315   -0.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9874    0.5283    0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4225    0.3208    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0925    1.0180   -0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3360    0.4868   -0.9258 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4186   -0.5171   -0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2626   -0.6398    0.6329 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7052   -1.7410    0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1798   -0.0335    1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1159    1.6203    0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033    1.8358   -1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3145   -1.1320    0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9672   -1.2672    1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  6 13  1  0
  8 14  1  0
  9 15  1  0
M  END
Download

3D SDF for NP0000427 (Imidazoleacetic acid)


  Mrv1652305271900162D          

  9  9  0  0  0  0            999 V2000
   19.3428   -4.0814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3866   -3.0196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4930   -4.6085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0805   -3.3391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1604   -4.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9451   -4.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9055   -3.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8255   -4.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5581   -3.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  3  5  1  0  0  0  0
  3  8  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000427

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC1=CN=CN1

> <INCHI_IDENTIFIER>
InChI=1S/C5H6N2O2/c8-5(9)1-4-2-6-3-7-4/h2-3H,1H2,(H,6,7)(H,8,9)

> <INCHI_KEY>
PRJKNHOMHKJCEJ-UHFFFAOYSA-N

> <FORMULA>
C5H6N2O2

> <MOLECULAR_WEIGHT>
126.1133

> <EXACT_MASS>
126.042927446

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.472699109880597

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.50

> <JCHEM_LOGP>
-1.3990613301983859

> <ALOGPS_LOGS>
-0.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.995890284546483

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6538030747064596

> <JCHEM_PKA_STRONGEST_BASIC>
6.776708441179222

> <JCHEM_POLAR_SURFACE_AREA>
65.97999999999999

> <JCHEM_REFRACTIVITY>
30.197899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.33e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
IMAC

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000427 (Imidazoleacetic acid)

HMDB0002024
     RDKit          3D
Imidazoleacetic acid
 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.1351    0.7461   -1.4990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9127    0.0057   -0.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810   -1.2315   -0.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9874    0.5283    0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4225    0.3208    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0925    1.0180   -0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3360    0.4868   -0.9258 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4186   -0.5171   -0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2626   -0.6398    0.6329 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7052   -1.7410    0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1798   -0.0335    1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1159    1.6203    0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033    1.8358   -1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3145   -1.1320    0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9672   -1.2672    1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  6 13  1  0
  8 14  1  0
  9 15  1  0
M  END
Download

PDB for NP0000427 (Imidazoleacetic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      36.107  -7.619   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      34.322  -5.637   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      30.787  -8.603   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      30.017  -6.233   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      32.033  -7.697   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.498  -8.173   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.557  -6.233   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.541  -7.697   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      34.642  -7.143   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3    5    8                                                       
CONECT    4    7    8                                                       
CONECT    5    3    6    7                                                  
CONECT    6    5    9                                                       
CONECT    7    4    5                                                       
CONECT    8    3    4                                                       
CONECT    9    1    2    6                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for NP0000427 (Imidazoleacetic acid)

COMPND    HMDB0002024
HETATM    1  O1  UNL     1      -2.135   0.746  -1.499  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.913   0.006  -0.483  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.481  -1.231  -0.349  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.987   0.528   0.564  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.423   0.321   0.107  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.092   1.018  -0.861  1.00  0.00           C  
HETATM    7  N1  UNL     1       2.336   0.487  -0.926  1.00  0.00           N  
HETATM    8  C5  UNL     1       2.419  -0.517  -0.016  1.00  0.00           C  
HETATM    9  N2  UNL     1       1.263  -0.640   0.633  1.00  0.00           N  
HETATM   10  H1  UNL     1      -2.705  -1.741   0.509  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.180  -0.033   1.488  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.116   1.620   0.744  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.703   1.836  -1.476  1.00  0.00           H  
HETATM   14  H5  UNL     1       3.314  -1.132   0.178  1.00  0.00           H  
HETATM   15  H6  UNL     1       0.967  -1.267   1.387  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   10
CONECT    4    5   11   12
CONECT    5    6    6    9
CONECT    6    7   13
CONECT    7    8    8
CONECT    8    9   14
CONECT    9   15
END
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SMILES for NP0000427 (Imidazoleacetic acid)

OC(=O)CC1=CN=CN1
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INCHI for NP0000427 (Imidazoleacetic acid)

InChI=1S/C5H6N2O2/c8-5(9)1-4-2-6-3-7-4/h2-3H,1H2,(H,6,7)(H,8,9)
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View in JSmol
Synonyms
ValueSource
1H-Imidazole-4-acetic acidChEBI
4(5)-ImidazoleacetateChEBI
4-ImidazoleacetateChEBI
Imidazole-4-acetateChEBI
1H-Imidazole-4-acetateGenerator
4(5)-Imidazoleacetic acidGenerator
4-Imidazoleacetic acidGenerator
Imidazole-4-acetic acidGenerator
ImidazoleacetateGenerator
1H-Imidazol-4-ylacetic acidHMDB
IAAHMDB
IMACHMDB
Imidazol-4-ylacetateHMDB
Imidazol-4-ylacetic acidHMDB
Imidazole acetateHMDB
Imidazolyl-4-acetic acidHMDB
IZCHMDB
Lopac-I-0375HMDB
Imidazole-4-acetic acid, sodium saltHMDB
Imidazole-4-acetic acid hydrochlorideHMDB
Chemical FormulaC5H6N2O2
Average Mass126.1133 Da
Monoisotopic Mass126.04293 Da
IUPAC Name2-(1H-imidazol-5-yl)acetic acid
Traditional NameIMAC
CAS Registry Number645-65-8
SMILES
OC(=O)CC1=CN=CN1
InChI Identifier
InChI=1S/C5H6N2O2/c8-5(9)1-4-2-6-3-7-4/h2-3H,1H2,(H,6,7)(H,8,9)
InChI KeyPRJKNHOMHKJCEJ-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Coprinopsis atramentariaLOTUS Database
Hippospongia communisLOTUS Database
Mus musculusLOTUS 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
  • 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility53.3 g/LALOGPS
logP-0.5ALOGPS
logP-1.4ChemAxon
logS-0.37ALOGPS
pKa (Strongest Acidic)3.65ChemAxon
pKa (Strongest Basic)6.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.98 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity30.2 m³·mol⁻¹ChemAxon
Polarizability11.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002024
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030508
KNApSAcK IDNot Available
Chemspider ID86856
KEGG Compound IDC02835
BioCyc ID4-IMIDAZOLEACETATE
BiGG ID40666
Wikipedia LinkNot Available
METLIN ID6445
PubChem Compound96215
PDB IDNot Available
ChEBI ID16974
Good Scents IDNot Available
References
General References
  1. Khandelwal JK, Prell GD, Morrishow AM, Green JP: Presence and measurement of imidazoleacetic acid, a gamma-aminobutyric acid agonist, in rat brain and human cerebrospinal fluid. J Neurochem. 1989 Apr;52(4):1107-13. [PubMed:2926392 ]
  2. 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 ]
  3. 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 ]
  4. Sondergaard I: Quantitative determination of 1,4-methyl-imidazoleacetic acid in urine by high performance liquid chromatography. Allergy. 1982 Nov;37(8):581-6. [PubMed:7181054 ]
  5. Imamura I, Watanabe T, Hase Y, Sakamoto Y, Fukuda Y, Yamamoto H, Tsuruhara T, Wada H: Histamine metabolism in patients with histidinemia: determination of urinary levels of histamine, N tau-methylhistamine, imidazole acetic acid, and its conjugate(s). J Biochem. 1984 Dec;96(6):1925-9. [PubMed:6530403 ]
  6. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]