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Showing metabocard for Imidazole-4-acetaldehyde (HMDB0003905)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (7) Show 7 proteinsXML
enzymes (7) Show 7 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 07:02:23 UTC
Update Date2023-02-21 17:16:50 UTC
HMDB IDHMDB0003905
Secondary Accession Numbers
  • HMDB0006237
  • HMDB03905
  • HMDB06237
Metabolite 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. 1.4.3.6), and can be synthesized by oxidation of histidine.
Structure
Data?1676999810
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003905 (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 HMDB0003905 (Imidazole-4-acetaldehyde)

HMDB0003905
     RDKit          3D
Imidazole-4-acetaldehyde
 14 14  0  0  0  0  0  0  0  0999 V2000
    1.3634    1.8333   -0.3783 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9735    0.7830   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3099   -0.5359   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1717   -0.2985   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0543   -0.2903   -1.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2717   -0.0427   -0.5738 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1944    0.1039    0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9023   -0.0547    1.0715 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0515    0.8338   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5217   -1.1193   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6620   -1.0674    0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7901   -0.4567   -2.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0065    0.3137    1.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4910   -0.0024    2.0314 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
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3D SDF for HMDB0003905 (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>
HMDB0003905

> <DATABASE_NAME>
hmdb

> <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 HMDB0003905 (Imidazole-4-acetaldehyde)

HMDB0003905
     RDKit          3D
Imidazole-4-acetaldehyde
 14 14  0  0  0  0  0  0  0  0999 V2000
    1.3634    1.8333   -0.3783 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9735    0.7830   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3099   -0.5359   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1717   -0.2985   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0543   -0.2903   -1.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2717   -0.0427   -0.5738 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1944    0.1039    0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9023   -0.0547    1.0715 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0515    0.8338   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5217   -1.1193   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6620   -1.0674    0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7901   -0.4567   -2.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0065    0.3137    1.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4910   -0.0024    2.0314 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
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PDB for HMDB0003905 (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 HMDB0003905 (Imidazole-4-acetaldehyde)

COMPND    HMDB0003905
HETATM    1  O1  UNL     1       1.363   1.833  -0.378  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.973   0.783  -0.312  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.310  -0.536  -0.118  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.172  -0.298  -0.028  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.054  -0.290  -1.085  1.00  0.00           C  
HETATM    6  N1  UNL     1      -2.272  -0.043  -0.574  1.00  0.00           N  
HETATM    7  C5  UNL     1      -2.194   0.104   0.747  1.00  0.00           C  
HETATM    8  N2  UNL     1      -0.902  -0.055   1.071  1.00  0.00           N  
HETATM    9  H1  UNL     1       3.051   0.834  -0.401  1.00  0.00           H  
HETATM   10  H2  UNL     1       1.522  -1.119  -1.062  1.00  0.00           H  
HETATM   11  H3  UNL     1       1.662  -1.067   0.784  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.790  -0.457  -2.135  1.00  0.00           H  
HETATM   13  H5  UNL     1      -3.006   0.314   1.460  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.491  -0.002   2.031  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    9
CONECT    3    4   10   11
CONECT    4    5    5    8
CONECT    5    6   12
CONECT    6    7    7
CONECT    7    8   13
CONECT    8   14
END
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SMILES for HMDB0003905 (Imidazole-4-acetaldehyde)

O=CCC1=CN=CN1
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INCHI for HMDB0003905 (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 JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1H-Imidazole-4-acetaldehydeChEBI
Imidazole acetaldehydeChEBI
1H-Imidazole-5-acetaldehydeHMDB
4-ImidazolylacetaldehydeHMDB
Imidazole-4(or 5)-acetaldehydeHMDB
Chemical FormulaC5H6N2O
Average Molecular Weight110.1139
Monoisotopic Molecular Weight110.048012824
IUPAC Name2-(1H-imidazol-5-yl)acetaldehyde
Traditional Name1H-imidazole-5-acetaldehyde
CAS Registry Number645-14-7
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
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
Ontology
Physiological effectNot Available
Disposition
Source
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.388Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility229 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+120.9931661259
DarkChem[M-H]-119.00931661259
DeepCCS[M+H]+121.79230932474
DeepCCS[M-H]-119.55330932474
DeepCCS[M-2H]-155.61330932474
DeepCCS[M+Na]+130.14530932474
AllCCS[M+H]+124.232859911
AllCCS[M+H-H2O]+119.332859911
AllCCS[M+NH4]+128.732859911
AllCCS[M+Na]+130.032859911
AllCCS[M-H]-120.632859911
AllCCS[M+Na-2H]-123.132859911
AllCCS[M+HCOO]-125.932859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.78 minutes32390414
Predicted by Siyang on May 30, 20228.3082 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.91 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid177.8 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid510.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid317.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid76.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid212.7 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid61.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid267.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid255.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)523.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid570.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid36.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid709.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid195.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid276.6 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate560.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA385.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water248.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Imidazole-4-acetaldehydeO=CCC1=CN=CN12199.7Standard polar33892256
Imidazole-4-acetaldehydeO=CCC1=CN=CN11277.6Standard non polar33892256
Imidazole-4-acetaldehydeO=CCC1=CN=CN11346.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Imidazole-4-acetaldehyde,1TMS,isomer #1C[Si](C)(C)OC=CC1=CN=C[NH]11489.8Semi standard non polar33892256
Imidazole-4-acetaldehyde,1TMS,isomer #1C[Si](C)(C)OC=CC1=CN=C[NH]11431.9Standard non polar33892256
Imidazole-4-acetaldehyde,1TMS,isomer #1C[Si](C)(C)OC=CC1=CN=C[NH]11935.4Standard polar33892256
Imidazole-4-acetaldehyde,1TMS,isomer #2C[Si](C)(C)N1C=NC=C1CC=O1401.5Semi standard non polar33892256
Imidazole-4-acetaldehyde,1TMS,isomer #2C[Si](C)(C)N1C=NC=C1CC=O1356.4Standard non polar33892256
Imidazole-4-acetaldehyde,1TMS,isomer #2C[Si](C)(C)N1C=NC=C1CC=O1821.5Standard polar33892256
Imidazole-4-acetaldehyde,2TMS,isomer #1C[Si](C)(C)OC=CC1=CN=CN1[Si](C)(C)C1607.6Semi standard non polar33892256
Imidazole-4-acetaldehyde,2TMS,isomer #1C[Si](C)(C)OC=CC1=CN=CN1[Si](C)(C)C1612.1Standard non polar33892256
Imidazole-4-acetaldehyde,2TMS,isomer #1C[Si](C)(C)OC=CC1=CN=CN1[Si](C)(C)C1828.3Standard polar33892256
Imidazole-4-acetaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CN=C[NH]11729.4Semi standard non polar33892256
Imidazole-4-acetaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CN=C[NH]11662.5Standard non polar33892256
Imidazole-4-acetaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CN=C[NH]12131.6Standard polar33892256
Imidazole-4-acetaldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC=C1CC=O1650.8Semi standard non polar33892256
Imidazole-4-acetaldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC=C1CC=O1579.6Standard non polar33892256
Imidazole-4-acetaldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC=C1CC=O1917.2Standard polar33892256
Imidazole-4-acetaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CN=CN1[Si](C)(C)C(C)(C)C2079.2Semi standard non polar33892256
Imidazole-4-acetaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CN=CN1[Si](C)(C)C(C)(C)C2035.9Standard non polar33892256
Imidazole-4-acetaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CN=CN1[Si](C)(C)C(C)(C)C2053.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Imidazole-4-acetaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9100000000-1efd54ea7ec2b730f5472017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Imidazole-4-acetaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazole-4-acetaldehyde 10V, Positive-QTOFsplash10-03di-3900000000-36122ec0895589b0d0bb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazole-4-acetaldehyde 20V, Positive-QTOFsplash10-03dl-9600000000-97998f328d98886138112017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazole-4-acetaldehyde 40V, Positive-QTOFsplash10-0uxr-9000000000-b240031657ec8c00b5b72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazole-4-acetaldehyde 10V, Negative-QTOFsplash10-0a4i-2900000000-80a13fb75d777746ebc02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazole-4-acetaldehyde 20V, Negative-QTOFsplash10-0a59-7900000000-2474bf70fe2a0a6443be2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazole-4-acetaldehyde 40V, Negative-QTOFsplash10-0006-9000000000-675428a404b9d1b09c692017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazole-4-acetaldehyde 10V, Positive-QTOFsplash10-03di-7900000000-c4f61368cc3619bb77732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazole-4-acetaldehyde 20V, Positive-QTOFsplash10-001i-9200000000-9e8c3dcfaaa09901cae92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazole-4-acetaldehyde 40V, Positive-QTOFsplash10-000x-9000000000-6a5e80237e5580be2b3b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazole-4-acetaldehyde 10V, Negative-QTOFsplash10-0a4i-5900000000-ebd2d5c38315d41944992021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazole-4-acetaldehyde 20V, Negative-QTOFsplash10-0159-9000000000-8c7dbf64d5cb9a0b87c92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imidazole-4-acetaldehyde 40V, Negative-QTOFsplash10-00kf-9000000000-ff96dfd23fb87b7cdc022021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDIM4ACT
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceShen, Chun; Yang, Lily; Miller, Stanley L.; Oro, J. Prebiotic synthesis of imidazole-4-acetaldehyde and histidine. Origins of Life and Evolution of the Biosphere (1987), 17(3-4), 295-305.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ambroziak W, Pietruszko R: Human aldehyde dehydrogenase. Activity with aldehyde metabolites of monoamines, diamines, and polyamines. J Biol Chem. 1991 Jul 15;266(20):13011-8. [PubMed:2071588 ]
  2. 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. [PubMed:2957640 ]
  3. Shen C, Yang L, Miller SL, Oro J: Prebiotic synthesis of histidine. J Mol Evol. 1990 Sep;31(3):167-74. [PubMed:11536478 ]

Enzymes

Enzyme Details
1. 4-trimethylaminobutyraldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Reactions
Imidazole-4-acetaldehyde + NAD + Water → Imidazoleacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
2. Alpha-aminoadipic semialdehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
Imidazole-4-acetaldehyde + NAD + Water → Imidazoleacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
3. Aldehyde dehydrogenase family 1 member A3
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Enzyme Details
4. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
Imidazole-4-acetaldehyde + NAD + Water → Imidazoleacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
5. Fatty aldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
Imidazole-4-acetaldehyde + NAD + Water → Imidazoleacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
6. Aldehyde dehydrogenase X, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
Imidazole-4-acetaldehyde + NAD + Water → Imidazoleacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
7. Amiloride-sensitive amine oxidase [copper-containing]
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
Reactions
Histamine + Water + Oxygen → Imidazole-4-acetaldehyde + Ammonia + Hydrogen peroxidedetails