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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:41:15 UTC
Update Date2022-03-07 02:57:12 UTC
HMDB IDHMDB0041826
Secondary Accession Numbers
  • HMDB41826
Metabolite Identification
Common NameAmifloxacin
DescriptionAmifloxacin, also known as WIN 49, belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Based on a literature review very few articles have been published on Amifloxacin.
Structure
Data?1563863706
Synonyms
ValueSource
WIN 49HMDB
6-Fluoro-1-methylamino-7-(4-methylpiperazin-1-yl)-1,4-dihydroquinolin-4-one-3-carboxylic acidHMDB
6-Fluoro-1-(methylamino)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylateGenerator
Chemical FormulaC16H19FN4O3
Average Molecular Weight334.3455
Monoisotopic Molecular Weight334.144118699
IUPAC Name6-fluoro-1-(methylamino)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Traditional Nameamifloxacin
CAS Registry Number86393-37-5
SMILES
CNN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N1CCN(C)CC1
InChI Identifier
InChI=1S/C16H19FN4O3/c1-18-21-9-11(16(23)24)15(22)10-7-12(17)14(8-13(10)21)20-5-3-19(2)4-6-20/h7-9,18H,3-6H2,1-2H3,(H,23,24)
InChI KeyRUXPNBWPIRDVTH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Macrolide
  • Dihydroxybenzoic acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Vinylogous acid
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Polyol
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.23Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.34 g/LALOGPS
logP-0.95ALOGPS
logP0.003ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)5.75ChemAxon
pKa (Strongest Basic)6.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area76.12 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity109.43 m³·mol⁻¹ChemAxon
Polarizability33.63 ųChemAxon
Number of Rings3ChemAxon
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-2H]-207.21330932474
DeepCCS[M+Na]+182.44130932474
AllCCS[M+H]+176.732859911
AllCCS[M+H-H2O]+173.532859911
AllCCS[M+NH4]+179.632859911
AllCCS[M+Na]+180.432859911
AllCCS[M-H]-180.332859911
AllCCS[M+Na-2H]-180.132859911
AllCCS[M+HCOO]-180.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AmifloxacinCNN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N1CCN(C)CC13713.4Standard polar33892256
AmifloxacinCNN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N1CCN(C)CC12691.0Standard non polar33892256
AmifloxacinCNN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N1CCN(C)CC13421.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Amifloxacin,1TMS,isomer #1CNN1C=C(C(=O)O[Si](C)(C)C)C(=O)C2=CC(F)=C(N3CCN(C)CC3)C=C213075.6Semi standard non polar33892256
Amifloxacin,1TMS,isomer #2CN1CCN(C2=CC3=C(C=C2F)C(=O)C(C(=O)O)=CN3N(C)[Si](C)(C)C)CC13020.4Semi standard non polar33892256
Amifloxacin,2TMS,isomer #1CN1CCN(C2=CC3=C(C=C2F)C(=O)C(C(=O)O[Si](C)(C)C)=CN3N(C)[Si](C)(C)C)CC12934.0Semi standard non polar33892256
Amifloxacin,2TMS,isomer #1CN1CCN(C2=CC3=C(C=C2F)C(=O)C(C(=O)O[Si](C)(C)C)=CN3N(C)[Si](C)(C)C)CC12847.4Standard non polar33892256
Amifloxacin,1TBDMS,isomer #1CNN1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CC(F)=C(N3CCN(C)CC3)C=C213294.6Semi standard non polar33892256
Amifloxacin,1TBDMS,isomer #2CN1CCN(C2=CC3=C(C=C2F)C(=O)C(C(=O)O)=CN3N(C)[Si](C)(C)C(C)(C)C)CC13227.8Semi standard non polar33892256
Amifloxacin,2TBDMS,isomer #1CN1CCN(C2=CC3=C(C=C2F)C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN3N(C)[Si](C)(C)C(C)(C)C)CC13341.7Semi standard non polar33892256
Amifloxacin,2TBDMS,isomer #1CN1CCN(C2=CC3=C(C=C2F)C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN3N(C)[Si](C)(C)C(C)(C)C)CC13244.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Amifloxacin GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1196000000-c099b7a45383fca98d882017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Amifloxacin GC-MS (1 TMS) - 70eV, Positivesplash10-0006-3019000000-90f7e83f8f87dca06adc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Amifloxacin 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 - Amifloxacin 10V, Positive-QTOFsplash10-00kr-0019000000-501310eec86d857ab7562017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amifloxacin 20V, Positive-QTOFsplash10-014r-0096000000-61989dd579c8fabf3d132017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amifloxacin 40V, Positive-QTOFsplash10-054x-2190000000-106d13fdca26738136092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amifloxacin 10V, Negative-QTOFsplash10-0019-0097000000-a6e164ac88ea3b386afb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amifloxacin 20V, Negative-QTOFsplash10-03di-1090000000-f62eaddef151127bb7e72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amifloxacin 40V, Negative-QTOFsplash10-08fr-2190000000-5c95ea74edded1217d062017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amifloxacin 10V, Positive-QTOFsplash10-00kr-0009000000-0077aeae67e44a1dc50e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amifloxacin 20V, Positive-QTOFsplash10-014r-0079000000-6bbff33dcecfbcde2a192021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amifloxacin 40V, Positive-QTOFsplash10-000i-2190000000-9edaa3ad6bfaeca4f7762021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amifloxacin 10V, Negative-QTOFsplash10-053r-0069000000-cd4c0937adc61d49f3ae2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amifloxacin 20V, Negative-QTOFsplash10-014i-0090000000-ddfc3f330c154b7ddca82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amifloxacin 40V, Negative-QTOFsplash10-0a59-0090000000-3ec71226f935a4d8c0022021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 ID50111
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmifloxacin
METLIN IDNot Available
PubChem Compound55492
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