MiMeDB: Showing metabocard for (R)-miconazole (MMDBc0054097)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:52:42 UTC

Update Date

2022-09-01 02:27:13 UTC

Metabolite ID

MMDBc0054097

Metabolite Identification

Common Name

(R)-miconazole

Description

(R)-miconazole belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene) (R)-miconazole is a very strong basic compound (based on its pKa). A 1-imidazole that has R configuration.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05041413142D          

 26 28  0  0  1  0            999 V2000
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5357   -2.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3427   -2.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -1.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1232   -1.9275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
 12  1  1  0  0  0  0
 12 10  1  0  0  0  0
 13  2  1  0  0  0  0
 13  7  2  0  0  0  0
 14  3  1  0  0  0  0
 14  8  2  0  0  0  0
 15  4  1  0  0  0  0
 16  7  1  0  0  0  0
 16 12  2  0  0  0  0
 17  8  1  0  0  0  0
 17 15  2  0  0  0  0
 18  9  1  0  0  0  0
 18 15  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23  5  1  0  0  0  0
 23 11  2  0  0  0  0
 24  6  1  0  0  0  0
 24  9  1  0  0  0  0
 24 11  1  0  0  0  0
 25 10  1  0  0  0  0
 18 25  1  6  0  0  0
 18 26  1  6  0  0  0
M  END


  Mrv0541 05041413142D          

 26 28  0  0  1  0            999 V2000
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5357   -2.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3427   -2.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -1.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1232   -1.9275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
 12  1  1  0  0  0  0
 12 10  1  0  0  0  0
 13  2  1  0  0  0  0
 13  7  2  0  0  0  0
 14  3  1  0  0  0  0
 14  8  2  0  0  0  0
 15  4  1  0  0  0  0
 16  7  1  0  0  0  0
 16 12  2  0  0  0  0
 17  8  1  0  0  0  0
 17 15  2  0  0  0  0
 18  9  1  0  0  0  0
 18 15  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23  5  1  0  0  0  0
 23 11  2  0  0  0  0
 24  6  1  0  0  0  0
 24  9  1  0  0  0  0
 24 11  1  0  0  0  0
 25 10  1  0  0  0  0
 18 25  1  6  0  0  0
 18 26  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054097

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](CN1C=CN=C1)(OCC1=C(Cl)C=C(Cl)C=C1)C1=C(Cl)C=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H14Cl4N2O/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22/h1-8,11,18H,9-10H2/t18-/m0/s1

> <INCHI_KEY>
BYBLEWFAAKGYCD-SFHVURJKSA-N

> <FORMULA>
C18H14Cl4N2O

> <MOLECULAR_WEIGHT>
416.129

> <EXACT_MASS>
413.986023908

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
39.72021613790989

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2R)-2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1H-imidazole

> <ALOGPS_LOGP>
5.86

> <JCHEM_LOGP>
5.956368360333332

> <ALOGPS_LOGS>
-5.74

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
6.767291901565906

> <JCHEM_POLAR_SURFACE_AREA>
27.05

> <JCHEM_REFRACTIVITY>
103.06759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.63e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
MCZ

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   20 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   21 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   22 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   23  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2   12                                                       
CONECT    2    1   13                                                       
CONECT    3    4   14                                                       
CONECT    4    3   15                                                       
CONECT    5    6   23                                                       
CONECT    6    5   24                                                       
CONECT    7   13   16                                                       
CONECT    8   14   17                                                       
CONECT    9   18   24                                                       
CONECT   10   12   25                                                       
CONECT   11   23   24                                                       
CONECT   12    1   10   16                                                  
CONECT   13    2    7   19                                                  
CONECT   14    3    8   20                                                  
CONECT   15    4   17   18                                                  
CONECT   16    7   12   21                                                  
CONECT   17    8   15   22                                                  
CONECT   18    9   15   25   26                                             
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23    5   11                                                       
CONECT   24    6    9   11                                                  
CONECT   25   10   18                                                       
CONECT   26   18                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

Synonyms

Not Available

Molecular Formula

C₁₈H₁₄Cl₄N₂O

Average Mass

416.129

Monoisotopic Mass

413.986023908

IUPAC Name

1-[(2R)-2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1H-imidazole

Traditional Name

MCZ

CAS Registry Number

Not Available

SMILES

[H][C@@](CN1C=CN=C1)(OCC1=C(Cl)C=C(Cl)C=C1)C1=C(Cl)C=C(Cl)C=C1

InChI Identifier

InChI=1S/C18H14Cl4N2O/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22/h1-8,11,18H,9-10H2/t18-/m0/s1

InChI Key

BYBLEWFAAKGYCD-SFHVURJKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzylethers

Direct Parent

Benzylethers

Alternative Parents

Substituents

Benzylether
1,3-dichlorobenzene
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
N-substituted imidazole
Imidazole
Azole
Heteroaromatic compound
Ether
Dialkyl ether
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole (CHEBI:82894 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00076 g/L	ALOGPS
logP	5.86	ALOGPS
logP	5.96	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	6.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.05 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	103.07 m³·mol⁻¹	ChemAxon
Polarizability	39.72 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	5

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

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

Not Available

METLIN ID

Not Available

PubChem Compound

1150344

PDB ID

Not Available

ChEBI ID

82894

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (R)-miconazole (MMDBc0054097)

MOL for #<Metabolite:0x00007fecf46fb038>

3D MOL for #<Metabolite:0x00007fecf46fb038>

3D SDF for #<Metabolite:0x00007fecf46fb038>

3D-SDF for #<Metabolite:0x00007fecf46fb038>

PDB for #<Metabolite:0x00007fecf46fb038>

3D PDB for #<Metabolite:0x00007fecf46fb038>

SMILES for #<Metabolite:0x00007fecf46fb038>

INCHI for #<Metabolite:0x00007fecf46fb038>

Structure for #<Metabolite:0x00007fecf46fb038>

3D Structure for #<Metabolite:0x00007fecf46fb038>