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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:14:20 UTC

Update Date

2022-09-22 18:35:01 UTC

HMDB ID

HMDB0341130

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Amiloride hydrochloride (Midamor)

Description

amiloride hydrochloride, also known as amiloride HCL, belongs to the class of organic compounds known as aminopyrazines. These are organic compounds containing an amino group attached to a pyrazine ring. amiloride hydrochloride is a drug. A hydrochloride obtained by combining amiloride with one molar equivalent of hydrochloric acid. amiloride hydrochloride is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

  Mrv1572004011623172D          

 16 15  0  0  0  0            999 V2000
   -1.0717    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3571   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    1.2374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3571    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3571    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8063   -0.7728    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1  9  2  0  0  0  0
  7  3  2  0  0  0  0
  3  2  1  0  0  0  0
  2  5  2  0  0  0  0
  5  9  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  9 14  1  0  0  0  0
 14 10  1  0  0  0  0
 10 12  1  0  0  0  0
 12 11  1  0  0  0  0
 12 13  2  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341130

> <DATABASE_NAME>
hmdb

> <SMILES>
Cl.NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N

> <INCHI_IDENTIFIER>
InChI=1S/C6H8ClN7O.ClH/c7-2-4(9)13-3(8)1(12-2)5(15)14-6(10)11;/h(H4,8,9,13)(H4,10,11,14,15);1H

> <INCHI_KEY>
ACHKKGDWZVCSNH-UHFFFAOYSA-N

> <FORMULA>
C6H9Cl2N7O

> <MOLECULAR_WEIGHT>
266.09

> <EXACT_MASS>
265.0245633

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
20.00873206622474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,5-diamino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide hydrochloride

> <ALOGPS_LOGP>
-0.48

> <JCHEM_LOGP>
-0.4954324606666666

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.813677301389493

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.426254300962716

> <JCHEM_PKA_STRONGEST_BASIC>
7.3459099700062565

> <JCHEM_POLAR_SURFACE_AREA>
156.79

> <JCHEM_REFRACTIVITY>
67.18119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
amilorida hydrochloride

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-APR-16         0                                  
HETATM    1  N   UNK     0      -2.001   0.770   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0      -2.001  -2.310   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -3.334  -1.540   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -4.668  -2.310   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -0.667  -1.540   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.667  -2.310   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -3.334   0.000   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0      -4.668   0.770   0.000  0.00  0.00          Cl+0
HETATM    9  C   UNK     0      -0.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.000   0.000   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       4.668   0.000   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.334   0.770   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.334   2.310   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       0.667   0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.667   2.310   0.000  0.00  0.00           O+0
HETATM   16 Cl   UNK     0       3.372  -1.443   0.000  0.00  0.00          Cl+0
CONECT    1    7    9                                                       
CONECT    2    3    5                                                       
CONECT    3    7    2    4                                                  
CONECT    4    3                                                            
CONECT    5    2    9    6                                                  
CONECT    6    5                                                            
CONECT    7    1    3    8                                                  
CONECT    8    7                                                            
CONECT    9    1    5   14                                                  
CONECT   10   14   12                                                       
CONECT   11   12                                                            
CONECT   12   10   11   13                                                  
CONECT   13   12                                                            
CONECT   14    9   10   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Amiloride chloride	ChEBI
Amiloride HCL	ChEBI
Amiloride hydrochloride anhydrous	ChEBI
Amiloride monohydrochloride	ChEBI
N-Amidino-3,5-diamino-6-chloropyrazinecarboxamide monohydrochloride	ChEBI
Amiloride hydrochloride	MeSH
Berolina brand OF amiloride hydrochloride	MeSH
Kaluril	MeSH
Merck sharp and dohme brand OF amiloride hydrochloride	MeSH
Amiloride hydrochloride, anhydrous	MeSH
Cahill may roberts brand OF amiloride hydrochloride	MeSH
Amiloberag	MeSH
Merck brand OF amiloride hydrochloride	MeSH
Trommsdorff brand OF amiloride hydrochloride	MeSH
Alphapharm brand OF amiloride hydrochloride	MeSH
Amiduret trom	MeSH
Douglas brand OF amiloride hydrochloride	MeSH
Hydrochloride, amiloride	MeSH
Amidal	MeSH
Trom, amiduret	MeSH
Anhydrous amiloride hydrochloride	MeSH
Hydrochloride, anhydrous amiloride	MeSH
Modamide	MeSH
Amiloride	MeSH
Amrad brand OF amiloride hydrochloride	MeSH
Midamor	MeSH
Midoride	MeSH

Chemical Formula

C₆H₉Cl₂N₇O

Average Molecular Weight

266.09

Monoisotopic Molecular Weight

265.0245633

IUPAC Name

3,5-diamino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide hydrochloride

Traditional Name

amilorida hydrochloride

CAS Registry Number

Not Available

SMILES

Cl.NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N

InChI Identifier

InChI=1S/C6H8ClN7O.ClH/c7-2-4(9)13-3(8)1(12-2)5(15)14-6(10)11;/h(H4,8,9,13)(H4,10,11,14,15);1H

InChI Key

ACHKKGDWZVCSNH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminopyrazines. These are organic compounds containing an amino group attached to a pyrazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Aminopyrazines

Alternative Parents

Substituents

Aminopyrazine
Aryl chloride
Aryl halide
Imidolactam
Heteroaromatic compound
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Organic nitrogen compound
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Imine
Organopnictogen compound
Hydrocarbon derivative
Hydrochloride
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

hydrochloride (CHEBI:84743 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.48	ALOGPS
logP	-0.5	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	11.43	ChemAxon
pKa (Strongest Basic)	7.35	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	156.79 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.18 m³·mol⁻¹	ChemAxon
Polarizability	20.01 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiloride hydrochloride (Midamor) LC-ESI-qTof , Positive-QTOF	splash10-0v4i-1691000000-c4842fe2c3070d6e90dd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiloride hydrochloride (Midamor) LC-ESI-qTof , Positive-QTOF	splash10-01b9-3900000000-3004ed4fd46223c9127f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiloride hydrochloride (Midamor) , positive-QTOF	splash10-001i-2980000000-0d961d121ac6e883cffc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amiloride hydrochloride (Midamor) , positive-QTOF	splash10-01b9-3900000000-3004ed4fd46223c9127f	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amiloride hydrochloride (Midamor) 10V, Positive-QTOF	splash10-014i-0090000000-0ceac3546ad8fd318e3f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amiloride hydrochloride (Midamor) 20V, Positive-QTOF	splash10-014i-0090000000-0ceac3546ad8fd318e3f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amiloride hydrochloride (Midamor) 40V, Positive-QTOF	splash10-014i-0090000000-0ceac3546ad8fd318e3f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amiloride hydrochloride (Midamor) 10V, Negative-QTOF	splash10-03di-0090000000-7c56c7caf3112080b618	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amiloride hydrochloride (Midamor) 20V, Negative-QTOF	splash10-03di-0090000000-7c56c7caf3112080b618	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amiloride hydrochloride (Midamor) 40V, Negative-QTOF	splash10-03di-0090000000-7c56c7caf3112080b618	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DBSALT001807

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amiloride

METLIN ID

Not Available

PubChem Compound

16230

PDB ID

Not Available

ChEBI ID

84743

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Neto FC, Raftery D: Expanding Urinary Metabolite Annotation through Integrated Mass Spectral Similarity Networking. Anal Chem. 2021 Sep 7;93(35):12001-12010. doi: 10.1021/acs.analchem.1c02041. Epub 2021 Aug 26. [PubMed:34436864 ]

Showing metabocard for Amiloride hydrochloride (Midamor) (HMDB0341130)

MOL for HMDB0341130 (Amiloride hydrochloride (Midamor))

3D MOL for HMDB0341130 (Amiloride hydrochloride (Midamor))

3D SDF for HMDB0341130 (Amiloride hydrochloride (Midamor))

3D-SDF for HMDB0341130 (Amiloride hydrochloride (Midamor))

PDB for HMDB0341130 (Amiloride hydrochloride (Midamor))

3D PDB for HMDB0341130 (Amiloride hydrochloride (Midamor))

SMILES for HMDB0341130 (Amiloride hydrochloride (Midamor))

INCHI for HMDB0341130 (Amiloride hydrochloride (Midamor))

Structure for HMDB0341130 (Amiloride hydrochloride (Midamor))

3D Structure for HMDB0341130 (Amiloride hydrochloride (Midamor))

Predicted Kovats Retention Indices

MS/MS Spectra