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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:19 UTC
HMDB IDHMDB0015286
Secondary Accession Numbers
  • HMDB15286
Metabolite Identification
Common NameGemifloxacin
DescriptionGemifloxacin, also known as factiv, 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. Gemifloxacin is a drug which is used for the treatment of bacterial infection caused by susceptible strains such as s. pneumoniae, h. influenzae, h. parainfluenzae, or m. catarrhalis, s. pneumoniae (including multi-drug resistant strains [mdrsp]), m. pneumoniae, c. pneumoniae, or k. pneumoniae. Based on a literature review a significant number of articles have been published on Gemifloxacin.
Structure
Data?1582753279
Synonyms
ValueSource
FactivKegg
Gemifloxacin mesilateHMDB
Gemifloxacin mesylateHMDB
7-(3-Aminomethyl-4-methoxyimino-pyrrolidine-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-(1,8)-naphthyridine-3-carboxylic acidHMDB
FactiveHMDB
Chemical FormulaC18H20FN5O4
Average Molecular Weight389.3809
Monoisotopic Molecular Weight389.149932358
IUPAC Name7-[(4Z)-3-(aminomethyl)-4-(methoxyimino)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Traditional Namegemifloxacin
CAS Registry Number175463-14-6
SMILES
CO\N=C1/CN(CC1CN)C1=NC2=C(C=C1F)C(=O)C(=CN2C1CC1)C(O)=O
InChI Identifier
InChI=1S/C18H20FN5O4/c1-28-22-14-8-23(6-9(14)5-20)17-13(19)4-11-15(25)12(18(26)27)7-24(10-2-3-10)16(11)21-17/h4,7,9-10H,2-3,5-6,8,20H2,1H3,(H,26,27)/b22-14+
InChI KeyZRCVYEYHRGVLOC-HYARGMPZSA-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
  • Imidolactam
  • Pyridine
  • Aryl fluoride
  • Aryl halide
  • Heteroaromatic compound
  • Vinylogous amide
  • Pyrrolidine
  • Amino acid
  • Amino acid or derivatives
  • Oxime ether
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organohalogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.21 g/LNot Available
LogP2.3Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP10(-0.82) g/LALOGPS
logP10(-0.92) g/LChemAxon
logS10(-3.3) g/LALOGPS
pKa (Strongest Acidic)5.53ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area121.35 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity99.74 m³·mol⁻¹ChemAxon
Polarizability39.3 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gemifloxacin,1TMS,#1CO/N=C1\CN(C2=NC3=C(C=C2F)C(=O)C(C(=O)O[Si](C)(C)C)=CN3C2CC2)CC1CN3367.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gemifloxacin,1TMS,#2CO/N=C1\CN(C2=NC3=C(C=C2F)C(=O)C(C(=O)O)=CN3C2CC2)CC1CN[Si](C)(C)C3541.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gemifloxacin,1TBDMS,#1CO/N=C1\CN(C2=NC3=C(C=C2F)C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN3C2CC2)CC1CN3582.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gemifloxacin,1TBDMS,#2CO/N=C1\CN(C2=NC3=C(C=C2F)C(=O)C(C(=O)O)=CN3C2CC2)CC1CN[Si](C)(C)C(C)(C)C3715.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra
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 DB01155 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01155 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01155
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7845573
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGemifloxacin
METLIN IDNot Available
PubChem Compound9571107
PDB IDNot Available
ChEBI ID101853
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