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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 18:11:33 UTC
Update Date2019-07-23 07:14:45 UTC
HMDB IDHMDB0060633
Secondary Accession Numbers
  • HMDB60633
Metabolite Identification
Common NameN-Acetyl gemifloxacin
DescriptionN-Acetyl gemifloxacin belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. Naphthyridine carboxylic acids and derivatives are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group. N-Acetyl gemifloxacin is a moderately basic compound (based on its pKa). N-Acetyl gemifloxacin is a metabolite of gemifloxacin. Gemifloxacin mesylate (trade name Factive, Oscient Pharmaceuticals) is an oral broad-spectrum quinolone antibacterial agent used in the treatment of acute bacterial exacerbation of chronic bronchitis and mild-to-moderate pneumonia. Oscient Pharmaceuticals has licensed the active ingredient from LG Life Sciences of Korea.
Structure
Data?1563866085
SynonymsNot Available
Chemical FormulaC19H20FN5O5
Average Molecular Weight417.391
Monoisotopic Molecular Weight417.14484698
IUPAC Name1-cyclopropyl-7-[(4E)-3-acetamido-4-(methoxyimino)pyrrolidin-1-yl]-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Traditional Name1-cyclopropyl-7-[(4E)-3-acetamido-4-(methoxyimino)pyrrolidin-1-yl]-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid
CAS Registry NumberNot Available
SMILES
CO\N=C1/CN(CC1NC(C)=O)C1=NC2=C(C=C1F)C(=O)C(=CN2C1CC1)C(O)=O
InChI Identifier
InChI=1S/C19H20FN5O5/c1-9(26)21-14-7-24(8-15(14)23-30-2)18-13(20)5-11-16(27)12(19(28)29)6-25(10-3-4-10)17(11)22-18/h5-6,10,14H,3-4,7-8H2,1-2H3,(H,21,26)(H,28,29)/b23-15+
InChI KeyZLRGFKRHAFQIIT-HZHRSRAPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. Naphthyridine carboxylic acids and derivatives are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassNaphthyridines
Direct ParentNaphthyridine carboxylic acids and derivatives
Alternative Parents
Substituents
  • Naphthyridine carboxylic acid
  • Fluoroquinolone
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Dialkylarylamine
  • Aminopyridine
  • Aryl fluoride
  • Aryl halide
  • Imidolactam
  • Pyridine
  • Heteroaromatic compound
  • Acetamide
  • Vinylogous amide
  • Pyrrolidine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Oxime ether
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP0.26ALOGPS
logP1.19ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)5.83ChemAxon
pKa (Strongest Basic)2.67ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area124.43 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity104.17 m³·mol⁻¹ChemAxon
Polarizability41.29 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+192.04130932474
DeepCCS[M-H]-189.68430932474
DeepCCS[M-2H]-223.330932474
DeepCCS[M+Na]+198.52930932474
AllCCS[M+H]+193.432859911
AllCCS[M+H-H2O]+191.032859911
AllCCS[M+NH4]+195.532859911
AllCCS[M+Na]+196.232859911
AllCCS[M-H]-194.032859911
AllCCS[M+Na-2H]-194.132859911
AllCCS[M+HCOO]-194.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Acetyl gemifloxacinCO\N=C1/CN(CC1NC(C)=O)C1=NC2=C(C=C1F)C(=O)C(=CN2C1CC1)C(O)=O3868.3Standard polar33892256
N-Acetyl gemifloxacinCO\N=C1/CN(CC1NC(C)=O)C1=NC2=C(C=C1F)C(=O)C(=CN2C1CC1)C(O)=O3226.5Standard non polar33892256
N-Acetyl gemifloxacinCO\N=C1/CN(CC1NC(C)=O)C1=NC2=C(C=C1F)C(=O)C(=CN2C1CC1)C(O)=O3712.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetyl gemifloxacin,1TMS,isomer #1CO/N=C1\CN(C2=NC3=C(C=C2F)C(=O)C(C(=O)O[Si](C)(C)C)=CN3C2CC2)CC1NC(C)=O3586.5Semi standard non polar33892256
N-Acetyl gemifloxacin,1TMS,isomer #2CO/N=C1\CN(C2=NC3=C(C=C2F)C(=O)C(C(=O)O)=CN3C2CC2)CC1N(C(C)=O)[Si](C)(C)C3474.8Semi standard non polar33892256
N-Acetyl gemifloxacin,2TMS,isomer #1CO/N=C1\CN(C2=NC3=C(C=C2F)C(=O)C(C(=O)O[Si](C)(C)C)=CN3C2CC2)CC1N(C(C)=O)[Si](C)(C)C3346.1Semi standard non polar33892256
N-Acetyl gemifloxacin,2TMS,isomer #1CO/N=C1\CN(C2=NC3=C(C=C2F)C(=O)C(C(=O)O[Si](C)(C)C)=CN3C2CC2)CC1N(C(C)=O)[Si](C)(C)C3260.4Standard non polar33892256
N-Acetyl gemifloxacin,2TMS,isomer #1CO/N=C1\CN(C2=NC3=C(C=C2F)C(=O)C(C(=O)O[Si](C)(C)C)=CN3C2CC2)CC1N(C(C)=O)[Si](C)(C)C4653.4Standard polar33892256
N-Acetyl gemifloxacin,1TBDMS,isomer #1CO/N=C1\CN(C2=NC3=C(C=C2F)C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN3C2CC2)CC1NC(C)=O3783.6Semi standard non polar33892256
N-Acetyl gemifloxacin,1TBDMS,isomer #2CO/N=C1\CN(C2=NC3=C(C=C2F)C(=O)C(C(=O)O)=CN3C2CC2)CC1N(C(C)=O)[Si](C)(C)C(C)(C)C3692.7Semi standard non polar33892256
N-Acetyl gemifloxacin,2TBDMS,isomer #1CO/N=C1\CN(C2=NC3=C(C=C2F)C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN3C2CC2)CC1N(C(C)=O)[Si](C)(C)C(C)(C)C3730.9Semi standard non polar33892256
N-Acetyl gemifloxacin,2TBDMS,isomer #1CO/N=C1\CN(C2=NC3=C(C=C2F)C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN3C2CC2)CC1N(C(C)=O)[Si](C)(C)C(C)(C)C3660.7Standard non polar33892256
N-Acetyl gemifloxacin,2TBDMS,isomer #1CO/N=C1\CN(C2=NC3=C(C=C2F)C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN3C2CC2)CC1N(C(C)=O)[Si](C)(C)C(C)(C)C4628.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl gemifloxacin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-3009100000-94cb3ac698a93b0c53c22017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl gemifloxacin GC-MS (1 TMS) - 70eV, Positivesplash10-00di-3000900000-eb90c35e5a85960c00762017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl gemifloxacin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl gemifloxacin 10V, Positive-QTOFsplash10-0gb9-2007900000-0273034d20f2782a3c612017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl gemifloxacin 20V, Positive-QTOFsplash10-0fk9-1009100000-3e3f83fcdc2d6d97b9d32017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl gemifloxacin 40V, Positive-QTOFsplash10-03di-9305000000-bae6e029a4bafcf0f7e92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl gemifloxacin 10V, Negative-QTOFsplash10-00xr-0009200000-1d4a348ea763d49b5ab22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl gemifloxacin 20V, Negative-QTOFsplash10-0006-0019000000-6c2c03d923496ec76efc2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl gemifloxacin 40V, Negative-QTOFsplash10-00dl-6119000000-c937700cb8756ab490f72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl gemifloxacin 10V, Positive-QTOFsplash10-0690-0009800000-177936f5f6cd47e5b9ca2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl gemifloxacin 20V, Positive-QTOFsplash10-0zfr-0009600000-8c3b66e48fc08775d8f82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl gemifloxacin 40V, Positive-QTOFsplash10-01t9-1059000000-53722baeb1341aae83482021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl gemifloxacin 10V, Negative-QTOFsplash10-00kf-0009200000-4f5966ce403db502b9bc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl gemifloxacin 20V, Negative-QTOFsplash10-0w4i-1009000000-2e0596c3c5e268b4a0002021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl gemifloxacin 40V, Negative-QTOFsplash10-00l6-4019000000-f1627efb34e13760f2982021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131769922
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available