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Showing NP-Card for 5-Aminoimidazole (NP0087092)

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Record Information
Version1.0
Created at2022-05-11 16:39:50 UTC
Updated at2022-05-11 16:39:50 UTC
NP-MRD IDNP0087092
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Aminoimidazole
Description5-Aminoimidazole belongs to the class of organic compounds known as aminoimidazoles. These are organic compounds containing an amino group linked to an imidazole ring. 5-Aminoimidazole is a very strong basic compound (based on its pKa). It was first documented in 1986 (PMID: 3740420). In humans, 5-aminoimidazole is involved in the metabolic disorder called the adenosine deaminase deficiency pathway (PMID: 16985054).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0087092 (5-Aminoimidazole)


  Mrv0541 02231219482D          

  6  6  0  0  0  0            999 V2000
   24.7566   -7.2725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3045   -7.5024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8919   -6.2328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9719   -7.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6371   -7.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7171   -6.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  5  2  0  0  0  0
  3  6  1  0  0  0  0
  4  6  2  0  0  0  0
M  END
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3D MOL for NP0087092 (5-Aminoimidazole)

     RDKit          3D

 11 11  0  0  0  0  0  0  0  0999 V2000
   -1.7975   -0.3011    0.1256 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4110    0.0436    0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1301    1.2900   -0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4525    1.1187   -0.1337 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7638   -0.1798   -0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6169   -0.8518   -0.0057 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4516    0.3699    0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0849   -1.2206   -0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3884    2.2185   -0.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7338   -0.6101   -0.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4362   -1.8773    0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  2  1  0
  1  7  1  0
  1  8  1  0
  3  9  1  0
  5 10  1  0
  6 11  1  0
M  END
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3D SDF for NP0087092 (5-Aminoimidazole)


  Mrv0541 02231219482D          

  6  6  0  0  0  0            999 V2000
   24.7566   -7.2725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3045   -7.5024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8919   -6.2328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9719   -7.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6371   -7.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7171   -6.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  5  2  0  0  0  0
  3  6  1  0  0  0  0
  4  6  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0087092

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=CN=CN1

> <INCHI_IDENTIFIER>
InChI=1S/C3H5N3/c4-3-1-5-2-6-3/h1-2H,4H2,(H,5,6)

> <INCHI_KEY>
QRZMXADUXZADTF-UHFFFAOYSA-N

> <FORMULA>
C3H5N3

> <MOLECULAR_WEIGHT>
83.0919

> <EXACT_MASS>
83.048347175

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
7.97001904798279

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H-imidazol-5-amine

> <ALOGPS_LOGP>
-1.08

> <JCHEM_LOGP>
-0.8848591523333333

> <ALOGPS_LOGS>
0.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.837397549237902

> <JCHEM_PKA_STRONGEST_BASIC>
8.35929265195974

> <JCHEM_POLAR_SURFACE_AREA>
54.7

> <JCHEM_REFRACTIVITY>
22.966499999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.19e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-aminoimidazole

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0087092 (5-Aminoimidazole)

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PDB for NP0087092 (5-Aminoimidazole)
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      46.212 -13.575   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0      43.502 -14.004   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      42.732 -11.635   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      44.748 -13.099   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      42.256 -13.099   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      44.272 -11.635   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    4    5                                                       
CONECT    3    5    6                                                       
CONECT    4    1    2    6                                                  
CONECT    5    2    3                                                       
CONECT    6    3    4                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   12    0
END

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3D PDB for NP0087092 (5-Aminoimidazole)
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SMILES for NP0087092 (5-Aminoimidazole)
NC1=CN=CN1
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INCHI for NP0087092 (5-Aminoimidazole)
InChI=1S/C3H5N3/c4-3-1-5-2-6-3/h1-2H,4H2,(H,5,6)
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Synonyms
ValueSource
AminoimidazoleKegg
4-AminoimidazoleKegg
5-AminoimidazoleChEBI
Chemical FormulaC3H5N3
Average Mass83.0919 Da
Monoisotopic Mass83.04835 Da
IUPAC Name1H-imidazol-5-amine
Traditional Name5-aminoimidazole
CAS Registry NumberNot Available
SMILES
NC1=CN=CN1
InChI Identifier
InChI=1S/C3H5N3/c4-3-1-5-2-6-3/h1-2H,4H2,(H,5,6)
InChI KeyQRZMXADUXZADTF-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 aminoimidazoles. These are organic compounds containing an amino group linked to an imidazole ring.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassAzoles  
Sub ClassImidazoles  
Direct ParentAminoimidazoles  
Alternative Parents
Substituents
  • Aminoimidazole
    • 

  • Heteroaromatic compound
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary amine
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • 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-1.1ALOGPS
logP-0.88ChemAxon
logS0.58ALOGPS
pKa (Strongest Acidic)13.84ChemAxon
pKa (Strongest Basic)8.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.7 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.97 m³·mol⁻¹ChemAxon
Polarizability7.97 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003929  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023250  
KNApSAcK IDNot Available
Chemspider ID470  
KEGG Compound IDC05239  
BioCyc IDCPD-54  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6989  
PubChem Compound484  
PDB IDNot Available
ChEBI ID16607  
Good Scents IDNot Available
References
General References
  1. Laikind PK, Seegmiller JE, Gruber HE: Detection of 5'-phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazole in urine by use of the Bratton-Marshall reaction: identification of patients deficient in adenylosuccinate lyase activity. Anal Biochem. 1986 Jul;156(1):81-90. doi: 10.1016/0003-2697(86)90158-2. [PubMed:3740420  ] 
  2. Beckers A, Organe S, Timmermans L, Vanderhoydonc F, Deboel L, Derua R, Waelkens E, Brusselmans K, Verhoeven G, Swinnen JV: Methotrexate enhances the antianabolic and antiproliferative effects of 5-aminoimidazole-4-carboxamide riboside. Mol Cancer Ther. 2006 Sep;5(9):2211-7. doi: 10.1158/1535-7163.MCT-06-0001. [PubMed:16985054  ]