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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:48:58 UTC

Update Date

2022-03-07 02:57:14 UTC

HMDB ID

HMDB0041938

Secondary Accession Numbers

HMDB41938

Metabolite Identification

Common Name

Moxonidine

Description

Moxonidine (INN) is a new generation centrally acting antihypertensive drug licensed for the treatment of mild to moderate essential hypertension. It may have a role when thiazides, beta-blockers, ACE inhibitors and calcium channel blockers are not appropriate or have failed to control blood pressure. In addition, it demonstrates favourable effects on parameters of the insulin resistance syndrome, apparently independent of blood pressure reduction. It is manufactured by Solvay Pharmaceuticals under the brand name Physiotens. Moxonidine is a selective agonist at the imidazoline receptor subtype 1 (I1). This receptor subtype is found in both the rostral ventro-lateral pressor and ventromedial depressor areas of the medulla oblongata. Moxonidine therefore causes a decrease in sympathetic nervous system activity and, therefore, a decrease in blood pressure.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 09131211492D          

 16 17  0  0  0  0            999 V2000
    5.0013    5.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309    2.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    2.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.9411    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4760    2.9812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109    2.9812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.9411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.7036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.2911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.4661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  3  1  0  0  0  0
 11  9  2  0  0  0  0
 12  4  1  0  0  0  0
 12  9  1  0  0  0  0
 13  5  2  0  0  0  0
 13  7  1  0  0  0  0
 14  5  1  0  0  0  0
 14  8  2  0  0  0  0
 15  6  1  0  0  0  0
 15  9  1  0  0  0  0
 16  2  1  0  0  0  0
 16  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041938

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=NC(C)=NC(Cl)=C1NC1=NCCN1

> <INCHI_IDENTIFIER>
InChI=1S/C9H12ClN5O/c1-5-13-7(10)6(8(14-5)16-2)15-9-11-3-4-12-9/h3-4H2,1-2H3,(H2,11,12,15)

> <INCHI_KEY>
WPNJAUFVNXKLIM-UHFFFAOYSA-N

> <FORMULA>
C9H12ClN5O

> <MOLECULAR_WEIGHT>
241.677

> <EXACT_MASS>
241.073037738

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
23.56614387041943

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxy-2-methylpyrimidin-5-amine

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
1.5387770663333333

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.2619138509713075

> <JCHEM_POLAR_SURFACE_AREA>
71.43

> <JCHEM_REFRACTIVITY>
63.41069999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
moxonidine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       9.336  11.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   5.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.231   4.100   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.771   4.100   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  10.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   8.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  10.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   8.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   6.470   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0       4.001  11.090   0.000  0.00  0.00          Cl+0
HETATM   11  N   UNK     0       2.755   5.565   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       5.247   5.565   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       6.668  11.090   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       8.002   8.780   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       4.001   8.010   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       6.668   6.470   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   16                                                            
CONECT    3    4   11                                                       
CONECT    4    3   12                                                       
CONECT    5    1   13   14                                                  
CONECT    6    7    8   15                                                  
CONECT    7    6   10   13                                                  
CONECT    8    6   14   16                                                  
CONECT    9   11   12   15                                                  
CONECT   10    7                                                            
CONECT   11    3    9                                                       
CONECT   12    4    9                                                       
CONECT   13    5    7                                                       
CONECT   14    5    8                                                       
CONECT   15    6    9                                                       
CONECT   16    2    8                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0041938
HETATM    1  C1  UNL     1      -1.316   3.090  -0.195  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.691   1.910  -0.608  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.228   0.649  -0.490  1.00  0.00           C  
HETATM    4  N1  UNL     1      -2.449   0.531   0.065  1.00  0.00           N  
HETATM    5  C3  UNL     1      -3.009  -0.678   0.199  1.00  0.00           C  
HETATM    6  C4  UNL     1      -4.377  -0.837   0.818  1.00  0.00           C  
HETATM    7  N2  UNL     1      -2.325  -1.751  -0.230  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.085  -1.665  -0.797  1.00  0.00           C  
HETATM    9 CL1  UNL     1      -0.257  -3.110  -1.332  1.00  0.00          CL  
HETATM   10  C6  UNL     1      -0.508  -0.428  -0.937  1.00  0.00           C  
HETATM   11  N3  UNL     1       0.764  -0.248  -1.509  1.00  0.00           N  
HETATM   12  C7  UNL     1       1.975  -0.253  -0.791  1.00  0.00           C  
HETATM   13  N4  UNL     1       2.898   0.646  -0.886  1.00  0.00           N  
HETATM   14  C8  UNL     1       4.014   0.363  -0.027  1.00  0.00           C  
HETATM   15  C9  UNL     1       3.804  -1.088   0.348  1.00  0.00           C  
HETATM   16  N5  UNL     1       2.378  -1.242   0.146  1.00  0.00           N  
HETATM   17  H1  UNL     1      -1.826   2.975   0.796  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.114   3.436  -0.892  1.00  0.00           H  
HETATM   19  H3  UNL     1      -0.526   3.854  -0.048  1.00  0.00           H  
HETATM   20  H4  UNL     1      -4.550   0.007   1.508  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.401  -1.826   1.304  1.00  0.00           H  
HETATM   22  H6  UNL     1      -5.106  -0.869  -0.018  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.809  -0.096  -2.562  1.00  0.00           H  
HETATM   24  H8  UNL     1       4.986   0.541  -0.528  1.00  0.00           H  
HETATM   25  H9  UNL     1       3.903   1.019   0.886  1.00  0.00           H  
HETATM   26  H10 UNL     1       4.378  -1.690  -0.418  1.00  0.00           H  
HETATM   27  H11 UNL     1       4.125  -1.314   1.377  1.00  0.00           H  
HETATM   28  H12 UNL     1       1.730  -1.926   0.577  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5
CONECT    5    6    7    7
CONECT    6   20   21   22
CONECT    7    8
CONECT    8    9   10   10
CONECT   10   11
CONECT   11   12   23
CONECT   12   13   13   16
CONECT   13   14
CONECT   14   15   24   25
CONECT   15   16   26   27
CONECT   16   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cynt	Kegg
Solvay brand OF moxonidine	HMDB
Moxon	HMDB
Zint	HMDB
4-Chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxy-2-methyl-5-pyrimidinamine	HMDB
Physiotens	HMDB
Lilly brand OF moxonidine	HMDB
Normatens	HMDB
Moxonidin	HMDB

Chemical Formula

C₉H₁₂ClN₅O

Average Molecular Weight

241.677

Monoisotopic Molecular Weight

241.073037738

IUPAC Name

4-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxy-2-methylpyrimidin-5-amine

Traditional Name

moxonidine

CAS Registry Number

75438-57-2

SMILES

COC1=NC(C)=NC(Cl)=C1NC1=NCCN1

InChI Identifier

InChI=1S/C9H12ClN5O/c1-5-13-7(10)6(8(14-5)16-2)15-9-11-3-4-12-9/h3-4H2,1-2H3,(H2,11,12,15)

InChI Key

WPNJAUFVNXKLIM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Halopyrimidines

Alternative Parents

Substituents

Alkyl aryl ether
Aminopyrimidine
Halopyrimidine
Aryl chloride
Aryl halide
Heteroaromatic compound
2-imidazoline
Guanidine
Ether
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrimidines (CHEBI:7009 )
organohalogen compound (CHEBI:7009 )

Ontology

Not Available

Not Available

Not Available

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
Water Solubility	0.11 g/L	ALOGPS
logP	1.01	ALOGPS
logP	1.54	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	7.26	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	71.43 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.41 m³·mol⁻¹	ChemAxon
Polarizability	23.57 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	149.17	30932474
DeepCCS	[M-H]-	146.812	30932474
DeepCCS	[M-2H]-	180.491	30932474
DeepCCS	[M+Na]+	155.316	30932474
AllCCS	[M+H]+	152.5	32859911
AllCCS	[M+H-H2O]+	148.7	32859911
AllCCS	[M+NH4]+	156.1	32859911
AllCCS	[M+Na]+	157.1	32859911
AllCCS	[M-H]-	152.4	32859911
AllCCS	[M+Na-2H]-	152.7	32859911
AllCCS	[M+HCOO]-	153.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Moxonidine	COC1=NC(C)=NC(Cl)=C1NC1=NCCN1	2897.2	Standard polar	33892256
Moxonidine	COC1=NC(C)=NC(Cl)=C1NC1=NCCN1	2047.4	Standard non polar	33892256
Moxonidine	COC1=NC(C)=NC(Cl)=C1NC1=NCCN1	2193.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Moxonidine,1TMS,isomer #1	COC1=NC(C)=NC(Cl)=C1N(C1=NCCN1)[Si](C)(C)C	2232.7	Semi standard non polar	33892256
Moxonidine,1TMS,isomer #1	COC1=NC(C)=NC(Cl)=C1N(C1=NCCN1)[Si](C)(C)C	2026.0	Standard non polar	33892256
Moxonidine,1TMS,isomer #2	COC1=NC(C)=NC(Cl)=C1NC1=NCCN1[Si](C)(C)C	2246.8	Semi standard non polar	33892256
Moxonidine,1TMS,isomer #2	COC1=NC(C)=NC(Cl)=C1NC1=NCCN1[Si](C)(C)C	2087.6	Standard non polar	33892256
Moxonidine,2TMS,isomer #1	COC1=NC(C)=NC(Cl)=C1N(C1=NCCN1[Si](C)(C)C)[Si](C)(C)C	2184.3	Semi standard non polar	33892256
Moxonidine,2TMS,isomer #1	COC1=NC(C)=NC(Cl)=C1N(C1=NCCN1[Si](C)(C)C)[Si](C)(C)C	2070.2	Standard non polar	33892256
Moxonidine,1TBDMS,isomer #1	COC1=NC(C)=NC(Cl)=C1N(C1=NCCN1)[Si](C)(C)C(C)(C)C	2415.3	Semi standard non polar	33892256
Moxonidine,1TBDMS,isomer #1	COC1=NC(C)=NC(Cl)=C1N(C1=NCCN1)[Si](C)(C)C(C)(C)C	2244.8	Standard non polar	33892256
Moxonidine,1TBDMS,isomer #2	COC1=NC(C)=NC(Cl)=C1NC1=NCCN1[Si](C)(C)C(C)(C)C	2488.8	Semi standard non polar	33892256
Moxonidine,1TBDMS,isomer #2	COC1=NC(C)=NC(Cl)=C1NC1=NCCN1[Si](C)(C)C(C)(C)C	2283.2	Standard non polar	33892256
Moxonidine,2TBDMS,isomer #1	COC1=NC(C)=NC(Cl)=C1N(C1=NCCN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2556.8	Semi standard non polar	33892256
Moxonidine,2TBDMS,isomer #1	COC1=NC(C)=NC(Cl)=C1N(C1=NCCN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2498.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Moxonidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01tc-5690000000-3b7abb53c5cb294edc13	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Moxonidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Moxonidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Moxonidine 35V, Positive-QTOF	splash10-0006-2390000000-80a3566b22396c07f5ef	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxonidine 10V, Positive-QTOF	splash10-0006-1190000000-041e81075a96626657ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxonidine 20V, Positive-QTOF	splash10-0006-3290000000-990323a69f256853945e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxonidine 40V, Positive-QTOF	splash10-014i-9400000000-5ddc520ccccf0f9bd5eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxonidine 10V, Negative-QTOF	splash10-0006-0190000000-605f75c37ceed4779ec3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxonidine 20V, Negative-QTOF	splash10-0lz0-9000000000-4f58efc26acea81dec40	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxonidine 40V, Negative-QTOF	splash10-08fr-5900000000-18fe1208405fe3f7f2dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxonidine 10V, Negative-QTOF	splash10-0006-0090000000-1a78e7e2eb750fe17c07	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxonidine 20V, Negative-QTOF	splash10-000y-9670000000-6b8cfc2f72e215593d1d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxonidine 40V, Negative-QTOF	splash10-00yi-9800000000-c825e291815059712c45	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxonidine 10V, Positive-QTOF	splash10-0006-0090000000-a95b289884284a22eb6e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxonidine 20V, Positive-QTOF	splash10-0006-0190000000-be5edad9a207b7a66fa5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxonidine 40V, Positive-QTOF	splash10-0006-8920000000-e3324ac8f4500e9046e0	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB09242

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4645

KEGG Compound ID

C07451

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Moxonidine

METLIN ID

Not Available

PubChem Compound

4810

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for Moxonidine (HMDB0041938)

MOL for HMDB0041938 (Moxonidine)

3D MOL for HMDB0041938 (Moxonidine)

3D SDF for HMDB0041938 (Moxonidine)

3D-SDF for HMDB0041938 (Moxonidine)

PDB for HMDB0041938 (Moxonidine)

3D PDB for HMDB0041938 (Moxonidine)

SMILES for HMDB0041938 (Moxonidine)

INCHI for HMDB0041938 (Moxonidine)

Structure for HMDB0041938 (Moxonidine)

3D Structure for HMDB0041938 (Moxonidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra