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Showing NP-Card for Betazole (NP0045129)

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Record Information
Version2.0
Created at2022-03-10 18:58:28 UTC
Updated at2022-03-10 22:18:40 UTC
NP-MRD IDNP0045129
Secondary Accession NumbersNone
Natural Product Identification
Common NameBetazole
DescriptionBetazole, also known as histalog or 96791, belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group. Betazole is a histamine H2 agonist, which is used clinically to test gastric secretory function. Gastritis can be diagnosed given late absence of gastric acid which is unresponsive to betazole stimulation. In humans, betazole is involved in betazole action pathway. Betazole can be used as a gastric secretory stimulant instead of histamine with the advantage of not provoking side effects and thus not requiring the use of antihistaminic compounds. Betazole is only found in individuals that have used or taken this drug. Surprisingly, betazole has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045129 (Betazole)

272
  Mrv1652303202019002D          

  8  8  0  0  0  0            999 V2000
    2.3174   -0.3790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.1481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.1059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695   -0.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9849    0.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3826    0.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7299    0.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9049    0.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
M  END
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3D MOL for NP0045129 (Betazole)

     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.8897   -0.1341    0.4300 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5161   -0.5488    0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6466    0.5110   -0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7848    0.1864   -0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8063    0.9688   -0.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9938    0.2975   -0.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6681   -0.8654    0.3147 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3351   -0.9239    0.4574 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0542    0.6533   -0.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5458   -0.8953    0.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.5069   -0.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327   -0.7601    1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0199    0.7098   -1.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8202    1.4474    0.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7344    1.9262   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9746    0.6752   -0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8569   -1.7412    0.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
M  END
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3D SDF for NP0045129 (Betazole)

272
  Mrv1652303202019002D          

  8  8  0  0  0  0            999 V2000
    2.3174   -0.3790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.1481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.1059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695   -0.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9849    0.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3826    0.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7299    0.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9049    0.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045129

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCC1=CC=NN1

> <INCHI_IDENTIFIER>
InChI=1S/C5H9N3/c6-3-1-5-2-4-7-8-5/h2,4H,1,3,6H2,(H,7,8)

> <INCHI_KEY>
JXDFEQONERDKSS-UHFFFAOYSA-N

> <FORMULA>
C5H9N3

> <MOLECULAR_WEIGHT>
111.1451

> <EXACT_MASS>
111.079647303

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
12.051820431587396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(1H-pyrazol-3-yl)ethan-1-amine

> <ALOGPS_LOGP>
-0.64

> <JCHEM_LOGP>
-0.27831712933333336

> <ALOGPS_LOGS>
0.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.157823213864614

> <JCHEM_PKA_STRONGEST_BASIC>
9.557087226236817

> <JCHEM_POLAR_SURFACE_AREA>
54.7

> <JCHEM_REFRACTIVITY>
32.396

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
betazole

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0045129 (Betazole)

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PDB for NP0045129 (Betazole)
HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 272                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  N   UNK     0       4.326  -0.707   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       9.645   0.276   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       3.080   0.198   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.036  -0.278   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.572   0.198   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.181   0.752   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.096   1.662   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.556   1.662   0.000  0.00  0.00           C+0
CONECT    1    3    5                                                       
CONECT    2    6                                                            
CONECT    3    1    8                                                       
CONECT    4    5    6                                                       
CONECT    5    1    4    7                                                  
CONECT    6    2    4                                                       
CONECT    7    5    8                                                       
CONECT    8    3    7                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

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3D PDB for NP0045129 (Betazole)
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SMILES for NP0045129 (Betazole)
NCCC1=CC=NN1
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INCHI for NP0045129 (Betazole)
InChI=1S/C5H9N3/c6-3-1-5-2-4-7-8-5/h2,4H,1,3,6H2,(H,7,8)
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Synonyms
ValueSource
1H-Pyrazole-3-ethanamineChEBI
2-(1H-Pyrazol-5-yl)ethanamineChEBI
2-(3-Pyrazolyl)ethylamineChEBI
3-(2-Aminoethyl)pyrazoleChEBI
3-(beta-Aminoethyl)pyrazoleChEBI
AmetazoleChEBI
BetazolChEBI
BetazolumChEBI
3-(b-Aminoethyl)pyrazoleGenerator
3-(Β-aminoethyl)pyrazoleGenerator
BetazoloHMDB
HistalogHMDB
96791, LillyHMDB
Lilly 96791HMDB
Betazole monohydrochlorideHMDB
Monohydrochloride, betazoleHMDB
Betazole dihydrochlorideHMDB
Dihydrochloride, betazoleHMDB
Chemical FormulaC5H9N3
Average Mass111.1451 Da
Monoisotopic Mass111.07965 Da
IUPAC Name2-(1H-pyrazol-3-yl)ethan-1-amine
Traditional Namebetazole
CAS Registry Number105-20-4
SMILES
NCCC1=CC=NN1
InChI Identifier
InChI=1S/C5H9N3/c6-3-1-5-2-4-7-8-5/h2,4H,1,3,6H2,(H,7,8)
InChI KeyJXDFEQONERDKSS-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
Cannabis sativaNULL
      Not Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group.
KingdomOrganic compounds  
Super ClassOrganic nitrogen compounds  
ClassOrganonitrogen compounds  
Sub ClassAmines  
Direct Parent2-arylethylamines  
Alternative Parents
Substituents
  • 2-arylethylamine
    • 

  • Aralkylamine
    • 

  • Heteroaromatic compound
    • 

  • Pyrazole
    • 

  • Azole
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary aliphatic 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-0.64ALOGPS
logP-0.28ChemAxon
logS0.15ALOGPS
pKa (Strongest Acidic)15.16ChemAxon
pKa (Strongest Basic)9.56ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.7 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.4 m³·mol⁻¹ChemAxon
Polarizability12.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0014417  
DrugBank IDDB00272  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7455  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBetazole  
METLIN IDNot Available
PubChem Compound7741  
PDB IDNot Available
ChEBI ID59170  
Good Scents IDNot Available
References
General References