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Showing NP-Card for Imidazole-4-acetaldehyde (NP0087091)

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Record Information
Version2.0
Created at2022-05-11 16:39:48 UTC
Updated at2022-05-11 16:39:48 UTC
NP-MRD IDNP0087091
Secondary Accession NumbersNone
Natural Product Identification
Common NameImidazole-4-acetaldehyde
DescriptionImidazole-4-acetaldehyde belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms. Imidazole-4-acetaldehyde is a very strong basic compound (based on its pKa). Imidazole-4-acetaldehyde exists in all living organisms, ranging from bacteria to humans. Within humans, imidazole-4-acetaldehyde participates in a number of enzymatic reactions. In particular, imidazole-4-acetaldehyde can be converted into imidazoleacetic acid; which is catalyzed by the enzyme aldehyde dehydrogenase, mitochondrial. In addition, imidazole-4-acetaldehyde can be biosynthesized from histamine; which is mediated by the enzyme amiloride-sensitive amine oxidase [copper-containing]. Imidazole-4-acetaldehyde could have been converted to histidine on the primitive earth by a Strecker synthesis, and several prebiotic reactions could convert imidazole-4-glycol and imidazole-4-ethanol to imidazole-4-acetaldehyde. In humans, imidazole-4-acetaldehyde is involved in histidine metabolism. Outside of the human body, Imidazole-4-acetaldehyde has been detected, but not quantified in, several different foods, such as pears, roselles, new zealand spinachs, calabash, and jew's ears. This could make imidazole-4-acetaldehyde a potential biomarker for the consumption of these foods. NAD-linked dehydrogenation of short chain aliphatic aldehydes has been found in virtually every organ of the mammalian body. Experimentally, the prebiotic formation of histidine has been accomplished by the reaction of erythrose with formamidine followed by a Strecker synthesis. Aldehyde dehydrogenase (EC1.2.1.3) Is the only enzyme in the human liver capable of catalyzing dehydrogenation of aldehydes arising via monoamine, diamine, and plasma amine oxidases. Imidazole-4-acetaldehyde is a good substrate for all aldehyde dehydrogenase isozymes. Imidazole-4-acetaldehyde is a naturally occurring aldehyde metabolite of histamine formed by the action of histaminase (E.C. Imidazole-4-acetaldehyde was first documented in 1987 (PMID: 2957640). 1.4.3.6), And can be synthesized by oxidation of histidine (PMID: 11536478).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0087091 (Imidazole-4-acetaldehyde)


  Mrv0541 02231219482D          

  8  8  0  0  0  0            999 V2000
   24.7207   -9.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7183  -10.9308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3058   -9.6612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1395  -10.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8070  -10.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3858  -10.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0509  -10.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1309   -9.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
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3D MOL for NP0087091 (Imidazole-4-acetaldehyde)

     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
   -1.5286    0.1719    1.7374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0645   -0.1734    0.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -0.2872   -0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1563    0.0750   -0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7328    1.3175   -0.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0311    1.1964   -0.0554 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3150   -0.0858    0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1543   -0.7449    0.0761 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1237   -0.3962    0.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6876    0.3108   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3008   -1.3485   -0.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2319    2.2403   -0.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2856   -0.5073    0.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0652   -1.7686    0.2328 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  7  2  0
  7  8  1  0
  8  4  1  0
  2  9  1  0
  3 10  1  0
  3 11  1  0
  5 12  1  0
  7 13  1  0
  8 14  1  0
M  END
Download

3D SDF for NP0087091 (Imidazole-4-acetaldehyde)


  Mrv0541 02231219482D          

  8  8  0  0  0  0            999 V2000
   24.7207   -9.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7183  -10.9308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3058   -9.6612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1395  -10.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8070  -10.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3858  -10.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0509  -10.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1309   -9.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0087091

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=CCC1=CN=CN1

> <INCHI_IDENTIFIER>
InChI=1S/C5H6N2O/c8-2-1-5-3-6-4-7-5/h2-4H,1H2,(H,6,7)

> <INCHI_KEY>
MQSRGWNVEZRLDK-UHFFFAOYSA-N

> <FORMULA>
C5H6N2O

> <MOLECULAR_WEIGHT>
110.1139

> <EXACT_MASS>
110.048012824

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
10.58134073700403

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.28

> <JCHEM_LOGP>
-0.7460910463333335

> <ALOGPS_LOGS>
0.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.174170924267564

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.789506665065463

> <JCHEM_PKA_STRONGEST_BASIC>
6.693379461750652

> <JCHEM_POLAR_SURFACE_AREA>
45.75

> <JCHEM_REFRACTIVITY>
29.272499999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.29e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1H-imidazole-5-acetaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0087091 (Imidazole-4-acetaldehyde)

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PDB for NP0087091 (Imidazole-4-acetaldehyde)
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      46.145 -17.688   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      42.407 -20.404   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      41.637 -18.034   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      45.060 -20.125   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      46.306 -19.220   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      43.653 -19.499   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      41.162 -19.499   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      43.178 -18.034   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    6    7                                                       
CONECT    3    7    8                                                       
CONECT    4    5    6                                                       
CONECT    5    1    4                                                       
CONECT    6    2    4    8                                                  
CONECT    7    2    3                                                       
CONECT    8    3    6                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

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3D PDB for NP0087091 (Imidazole-4-acetaldehyde)
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SMILES for NP0087091 (Imidazole-4-acetaldehyde)
O=CCC1=CN=CN1
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INCHI for NP0087091 (Imidazole-4-acetaldehyde)
InChI=1S/C5H6N2O/c8-2-1-5-3-6-4-7-5/h2-4H,1H2,(H,6,7)
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View in JSmol
Synonyms
ValueSource
1H-Imidazole-4-acetaldehydeChEBI
Imidazole acetaldehydeChEBI
1H-Imidazole-5-acetaldehydeHMDB
4-ImidazolylacetaldehydeHMDB
Imidazole-4(or 5)-acetaldehydeHMDB
Chemical FormulaC5H6N2O
Average Mass110.1139 Da
Monoisotopic Mass110.04801 Da
IUPAC Name2-(1H-imidazol-5-yl)acetaldehyde
Traditional Name1H-imidazole-5-acetaldehyde
CAS Registry NumberNot Available
SMILES
O=CCC1=CN=CN1
InChI Identifier
InChI=1S/C5H6N2O/c8-2-1-5-3-6-4-7-5/h2-4H,1H2,(H,6,7)
InChI KeyMQSRGWNVEZRLDK-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 imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassAzoles  
Sub ClassImidazoles  
Direct ParentImidazoles  
Alternative Parents
Substituents
  • Heteroaromatic compound
    • 

  • Imidazole
    • 

  • Alpha-hydrogen aldehyde
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Aldehyde
    • 

  • 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-0.28ALOGPS
logP-0.75ChemAxon
logS0.32ALOGPS
pKa (Strongest Acidic)11.79ChemAxon
pKa (Strongest Basic)6.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area45.75 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.27 m³·mol⁻¹ChemAxon
Polarizability10.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003905  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030915  
KNApSAcK IDNot Available
Chemspider ID132948  
KEGG Compound IDC05130  
BioCyc IDNot Available
BiGG ID45184  
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound150841  
PDB IDNot Available
ChEBI ID27398  
Good Scents IDNot Available
References
General References
  1. Shen C, Yang L, Miller SL, Oro J: Prebiotic synthesis of imidazole-4-acetaldehyde and histidine. Orig Life Evol Biosph. 1987;17(3-4):295-305. doi: 10.1007/BF02386469. [PubMed:2957640  ] 
  2. Shen C, Yang L, Miller SL, Oro J: Prebiotic synthesis of histidine. J Mol Evol. 1990 Sep;31(3):167-74. doi: 10.1007/BF02109492. [PubMed:11536478  ]