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Showing metabocard for Metronidazole (HMDB0015052)

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enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2023-02-21 17:18:22 UTC
HMDB IDHMDB0015052
Secondary Accession Numbers
  • HMDB15052
Metabolite Identification
Common NameMetronidazole
DescriptionMetronidazole, also known as metrogel-vaginal or flagyl, belongs to the class of organic compounds known as nitroimidazoles. Nitroimidazoles are compounds containing an imidazole ring which bears a nitro group. Metronidazole is a moderately basic compound (based on its pKa). Metronidazole is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.
Structure
Data?1676999902
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015052 (Metronidazole)

916
  Mrv1652305271900212D          

 12 12  0  0  0  0            999 V2000
    2.3876   -1.5382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1674    1.3064    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.7258   -0.0526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1022    0.5244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6897    1.7939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542    0.7543    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.1022   -0.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    1.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7696    1.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3876   -0.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5147    1.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2  6  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  8  2  0  0  0  0
  5 11  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 12  1  0  0  0  0
  9 11  2  0  0  0  0
M  CHG  2   2  -1   6   1
M  END
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3D MOL for HMDB0015052 (Metronidazole)

HMDB0015052
     RDKit          3D
Metronidazole
 21 21  0  0  0  0  0  0  0  0999 V2000
   -1.4378   -1.8268    0.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3297   -0.4085    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2214    0.5233    0.6474 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8183    1.6650    0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5998    1.4094   -0.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449    2.3885   -1.1965 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.2129    2.0892   -1.7368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2942    3.6703   -1.2703 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.3260    0.1080   -0.3418 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8149   -0.5838   -0.8246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9760   -0.5748    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6527   -1.1647    1.3443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0803   -1.8917    1.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9242   -2.5274    0.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5286   -2.1018    0.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3532    2.5983    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1847   -0.2437   -1.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5716   -1.6774   -0.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4317    0.4320    0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7765   -1.2046   -0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -0.6789    2.0632 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  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  9  2  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
 10 17  1  0
 10 18  1  0
 11 19  1  0
 11 20  1  0
 12 21  1  0
M  CHG  2   6   1   8  -1
M  END
Download

3D SDF for HMDB0015052 (Metronidazole)

916
  Mrv1652305271900212D          

 12 12  0  0  0  0            999 V2000
    2.3876   -1.5382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1674    1.3064    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.7258   -0.0526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1022    0.5244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6897    1.7939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542    0.7543    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.1022   -0.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    1.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7696    1.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3876   -0.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5147    1.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2  6  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  8  2  0  0  0  0
  5 11  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 12  1  0  0  0  0
  9 11  2  0  0  0  0
M  CHG  2   2  -1   6   1
M  END
> <DATABASE_ID>
HMDB0015052

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NC=C(N1CCO)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3

> <INCHI_KEY>
VAOCPAMSLUNLGC-UHFFFAOYSA-N

> <FORMULA>
C6H9N3O3

> <MOLECULAR_WEIGHT>
171.154

> <EXACT_MASS>
171.064391169

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.865661408610908

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol

> <ALOGPS_LOGP>
-0.15

> <JCHEM_LOGP>
-0.45931022466666654

> <ALOGPS_LOGS>
-1.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.4232507681049

> <JCHEM_PKA_STRONGEST_BASIC>
2.5709394271776644

> <JCHEM_POLAR_SURFACE_AREA>
81.19

> <JCHEM_REFRACTIVITY>
40.2163

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.92e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
metronidazole

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0015052 (Metronidazole)

HMDB0015052
     RDKit          3D
Metronidazole
 21 21  0  0  0  0  0  0  0  0999 V2000
   -1.4378   -1.8268    0.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3297   -0.4085    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2214    0.5233    0.6474 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8183    1.6650    0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5998    1.4094   -0.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449    2.3885   -1.1965 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.2129    2.0892   -1.7368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2942    3.6703   -1.2703 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.3260    0.1080   -0.3418 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8149   -0.5838   -0.8246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9760   -0.5748    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6527   -1.1647    1.3443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0803   -1.8917    1.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9242   -2.5274    0.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5286   -2.1018    0.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3532    2.5983    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1847   -0.2437   -1.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5716   -1.6774   -0.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4317    0.4320    0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7765   -1.2046   -0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -0.6789    2.0632 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  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  9  2  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
 10 17  1  0
 10 18  1  0
 11 19  1  0
 11 20  1  0
 12 21  1  0
M  CHG  2   6   1   8  -1
M  END
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PDB for HMDB0015052 (Metronidazole)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 916                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       4.457  -2.871   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.646   2.439   0.000  0.00  0.00           O-1
HETATM    3  O   UNK     0       8.821  -0.098   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       5.791   0.979   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       5.021   3.349   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.501   1.408   0.000  0.00  0.00           N+1
HETATM    7  C   UNK     0       5.791  -0.561   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.545   1.884   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.037   1.884   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.457  -1.331   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.561   3.349   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080   1.408   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    6                                                            
CONECT    3    6                                                            
CONECT    4    7    8    9                                                  
CONECT    5    8   11                                                       
CONECT    6    2    3    9                                                  
CONECT    7    4   10                                                       
CONECT    8    4    5   12                                                  
CONECT    9    4    6   11                                                  
CONECT   10    1    7                                                       
CONECT   11    5    9                                                       
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0015052 (Metronidazole)

COMPND    HMDB0015052
HETATM    1  C1  UNL     1      -1.438  -1.827   0.796  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.330  -0.408   0.370  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.221   0.523   0.647  1.00  0.00           N  
HETATM    4  C3  UNL     1      -1.818   1.665   0.123  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.600   1.409  -0.516  1.00  0.00           C  
HETATM    6  N2  UNL     1       0.145   2.388  -1.196  1.00  0.00           N1+
HETATM    7  O1  UNL     1       1.213   2.089  -1.737  1.00  0.00           O  
HETATM    8  O2  UNL     1      -0.294   3.670  -1.270  1.00  0.00           O1-
HETATM    9  N3  UNL     1      -0.326   0.108  -0.342  1.00  0.00           N  
HETATM   10  C5  UNL     1       0.815  -0.584  -0.825  1.00  0.00           C  
HETATM   11  C6  UNL     1       1.976  -0.575   0.146  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.653  -1.165   1.344  1.00  0.00           O  
HETATM   13  H1  UNL     1      -1.080  -1.892   1.841  1.00  0.00           H  
HETATM   14  H2  UNL     1      -0.924  -2.527   0.108  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.529  -2.102   0.729  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.353   2.598   0.193  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.185  -0.244  -1.817  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.572  -1.677  -0.983  1.00  0.00           H  
HETATM   19  H7  UNL     1       2.432   0.432   0.259  1.00  0.00           H  
HETATM   20  H8  UNL     1       2.777  -1.205  -0.327  1.00  0.00           H  
HETATM   21  H9  UNL     1       2.148  -0.679   2.063  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    3    9
CONECT    3    4
CONECT    4    5    5   16
CONECT    5    6    9
CONECT    6    7    7    8
CONECT    9   10
CONECT   10   11   17   18
CONECT   11   12   19   20
CONECT   12   21
END
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SMILES for HMDB0015052 (Metronidazole)

CC1=NC=C(N1CCO)[N+]([O-])=O
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INCHI for HMDB0015052 (Metronidazole)

InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1-(2-Hydroxy-1-ethyl)-2-methyl-5-nitroimidazoleChEBI
1-(2-Hydroxyethyl)-2-methyl-5-nitroimidazoleChEBI
1-(beta-Ethylol)-2-methyl-5-nitro-3-azapyrroleChEBI
1-(beta-Hydroxyethyl)-2-methyl-5-nitroimidazoleChEBI
1-(beta-Oxyethyl)-2-methyl-5-nitroimidazoleChEBI
2-Methyl-1-(2-hydroxyethyl)-5-nitroimidazoleChEBI
2-Methyl-3-(2-hydroxyethyl)-4-nitroimidazoleChEBI
2-Methyl-5-nitroimidazole-1-ethanolChEBI
MetronidazolChEBI
MetronidazolumChEBI
FlagylKegg
Metrogel-vaginalKegg
NoritateKegg
1-(b-Ethylol)-2-methyl-5-nitro-3-azapyrroleGenerator
1-(Β-ethylol)-2-methyl-5-nitro-3-azapyrroleGenerator
1-(b-Hydroxyethyl)-2-methyl-5-nitroimidazoleGenerator
1-(Β-hydroxyethyl)-2-methyl-5-nitroimidazoleGenerator
1-(b-Oxyethyl)-2-methyl-5-nitroimidazoleGenerator
1-(Β-oxyethyl)-2-methyl-5-nitroimidazoleGenerator
Noritic acidGenerator
MethronidazoleHMDB
Metronidazole benzoateHMDB
Metronidazole in plastic containerHMDB
MetronidazoloHMDB
DanizolHMDB
GineflavirHMDB
MetricHMDB
MetrodzhilHMDB
MetrogylHMDB
Metronidazole phosphoesterHMDB
Metronidazole hydrochlorideHMDB
Phosphoester, metronidazoleHMDB
2 Methyl 5 nitroimidazole 1 ethanolHMDB
ClontHMDB
Metronidazole phosphateHMDB
Phosphate, metronidazoleHMDB
TrivazolHMDB
Bayer 5360HMDB
Hydrochloride, metronidazoleHMDB
MetroGelHMDB
Metronidazole monohydrochlorideHMDB
Monohydrochloride, metronidazoleHMDB
SatricHMDB
TrichazolHMDB
TrichopolHMDB
VagilenHMDB
Chemical FormulaC6H9N3O3
Average Molecular Weight171.154
Monoisotopic Molecular Weight171.064391169
IUPAC Name2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol
Traditional Namemetronidazole
CAS Registry Number443-48-1
SMILES
CC1=NC=C(N1CCO)[N+]([O-])=O
InChI Identifier
InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
InChI KeyVAOCPAMSLUNLGC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitroimidazoles. Nitroimidazoles are compounds containing an imidazole ring which bears a nitro group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentNitroimidazoles
Alternative Parents
Substituents
  • 1,2,5-trisubstituted-imidazole
  • Nitroaromatic compound
  • Nitroimidazole
  • Trisubstituted imidazole
  • N-substituted imidazole
  • Heteroaromatic compound
  • Organic nitro compound
  • C-nitro compound
  • Alkanolamine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic zwitterion
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point160 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.92 g/LNot Available
LogP-0.1Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM132.430932474
[M+H]+Not Available130.38http://allccs.zhulab.cn/database/detail?ID=AllCCS00000933
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.92 g/LALOGPS
logP-0.15ALOGPS
logP-0.46ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)15.42ChemAxon
pKa (Strongest Basic)2.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area81.19 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity40.22 m³·mol⁻¹ChemAxon
Polarizability15.87 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+135.15831661259
DarkChem[M-H]-132.00231661259
DeepCCS[M+H]+136.20230932474
DeepCCS[M-H]-132.8630932474
DeepCCS[M-2H]-169.81830932474
DeepCCS[M+Na]+144.92430932474
AllCCS[M+H]+136.932859911
AllCCS[M+H-H2O]+132.732859911
AllCCS[M+NH4]+140.732859911
AllCCS[M+Na]+141.932859911
AllCCS[M-H]-133.532859911
AllCCS[M+Na-2H]-134.832859911
AllCCS[M+HCOO]-136.232859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.82 minutes32390414
Predicted by Siyang on May 30, 20229.6356 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.16 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid51.6 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1044.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid300.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid78.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid170.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid48.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid251.0 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid287.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)297.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid640.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid136.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1056.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid199.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid180.6 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate483.1 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA222.7 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water273.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MetronidazoleCC1=NC=C(N1CCO)[N+]([O-])=O2440.2Standard polar33892256
MetronidazoleCC1=NC=C(N1CCO)[N+]([O-])=O1557.9Standard non polar33892256
MetronidazoleCC1=NC=C(N1CCO)[N+]([O-])=O1666.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Metronidazole,1TMS,isomer #1CC1=NC=C([N+](=O)[O-])N1CCO[Si](C)(C)C1613.2Semi standard non polar33892256
Metronidazole,1TBDMS,isomer #1CC1=NC=C([N+](=O)[O-])N1CCO[Si](C)(C)C(C)(C)C1859.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Metronidazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udl-9700000000-f1b60dcdd221dbdf9eaa2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Metronidazole GC-MS (1 TMS) - 70eV, Positivesplash10-0fmi-9410000000-3cec2097481329b980542017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Metronidazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0ul0-9300000000-2268b08f47fed3f6d2632014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-QTOF , positive-QTOFsplash10-004i-1900000000-659f2bbb83f8ef5a85d12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOFsplash10-004i-0900000000-50c7cfe79eb17c4440a82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOFsplash10-00di-0900000000-b06d808767cc01c0d4942017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOFsplash10-00fr-0900000000-e9c07cc448b8fb5190222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOFsplash10-004i-0900000000-8ad03b44aa7557127e342017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOFsplash10-004i-0900000000-ed7ba5c872a6309a31d42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOFsplash10-004i-2900000000-e0ead4b0eec72b9c44b62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOFsplash10-004i-5900000000-2da8a7b45537f90632202017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOFsplash10-00di-0900000000-24d94f1704e577b05eb72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOFsplash10-00fr-0900000000-fbb1c4e8457cd3d799b92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOFsplash10-004i-0900000000-fd6166313a17f944f5302017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOFsplash10-004i-0900000000-5ebb32a580e1f5d001702017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOFsplash10-004i-2900000000-811a6e7e45b7ea1a61842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOFsplash10-004i-5900000000-082e6de6c0fa3f382d842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-ITFT , positive-QTOFsplash10-004i-0900000000-baf9e195c01d875e77b52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-QQ , positive-QTOFsplash10-00di-0900000000-ec181c008a10dac8040b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-QQ , positive-QTOFsplash10-004i-1900000000-2a218e19a8fadb9c66d62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-QQ , positive-QTOFsplash10-003r-9500000000-ed02acd36b190c189cc92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metronidazole LC-ESI-QQ , positive-QTOFsplash10-001i-9000000000-71ea79659ccd75c64bef2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metronidazole 10V, Positive-QTOFsplash10-00di-0900000000-b28839ace139ee8a385b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metronidazole 20V, Positive-QTOFsplash10-01ox-0900000000-94e5ccc473c03e521e892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metronidazole 40V, Positive-QTOFsplash10-01po-9500000000-64f688b22d9371ed56c12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metronidazole 10V, Negative-QTOFsplash10-00di-0900000000-5f65f2637682eccd62a22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metronidazole 20V, Negative-QTOFsplash10-05fu-3900000000-dbc213039f9c3a43948e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metronidazole 40V, Negative-QTOFsplash10-0007-9300000000-935f6b6b00b1b6b723b52016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00916 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00916 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00916
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4029
KEGG Compound IDC07203
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMetronidazole
METLIN IDNot Available
PubChem Compound4173
PDB ID2MN
ChEBI ID6909
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Visapaa JP, Tillonen JS, Kaihovaara PS, Salaspuro MP: Lack of disulfiram-like reaction with metronidazole and ethanol. Ann Pharmacother. 2002 Jun;36(6):971-4. [PubMed:12022894 ]
  2. Williams CS, Woodcock KR: Do ethanol and metronidazole interact to produce a disulfiram-like reaction? Ann Pharmacother. 2000 Feb;34(2):255-7. [PubMed:10676835 ]
  3. Lamont RF: Can antibiotics prevent preterm birth--the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. [PubMed:15715599 ]
  4. Shennan A, Crawshaw S, Briley A, Hawken J, Seed P, Jones G, Poston L: A randomised controlled trial of metronidazole for the prevention of preterm birth in women positive for cervicovaginal fetal fibronectin: the PREMET Study. BJOG. 2006 Jan;113(1):65-74. [PubMed:16398774 ]

Enzymes

Enzyme Details
1. Cytochrome P450 3A4
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
2. Cytochrome P450 2C9
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
3. Cytochrome P450 2C8
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]