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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2018-05-20 20:11:09 UTC
HMDB IDHMDB0014823
Secondary Accession Numbers
  • HMDB14823
Metabolite Identification
Common NameTrovafloxacin
DescriptionTrovafloxacin (sold as Trovan by Pfizer) is a broad spectrum antibiotic that inhibits the uncoiling of supercoiled DNA in various bacteria by blocking the activity of DNA gyrase and topoisomerase IV. It was withdrawn from the market due to the risk of hepatotoxicity. It had better gram-positive bacterial coverage and less gram-negative coverage than the previous fluoroquinolones. [Wikipedia]
Structure
Thumb
Synonyms
ValueSource
TVFXHMDB
Chemical FormulaC20H15F3N4O3
Average Molecular Weight416.3533
Monoisotopic Molecular Weight416.109624981
IUPAC Name7-[(1R,5S)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Traditional Nametrovafloxacin
CAS Registry Number147059-72-1
SMILES
[H][C@@]12CN(C[C@]1([H])C2N)C1=C(F)C=C2C(=O)C(=CN(C3=C(F)C=C(F)C=C3)C2=N1)C(O)=O
InChI Identifier
InChI=1S/C20H15F3N4O3/c21-8-1-2-15(13(22)3-8)27-7-12(20(29)30)17(28)9-4-14(23)19(25-18(9)27)26-5-10-11(6-26)16(10)24/h1-4,7,10-11,16H,5-6,24H2,(H,29,30)/t10-,11+,16?
InChI KeyWVPSKSLAZQPAKQ-SOSAQKQKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. These 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
  • 4-aminopiperidine
  • Aminopyridine
  • Halobenzene
  • Fluorobenzene
  • Aryl fluoride
  • Piperidine
  • Aryl halide
  • Monocyclic benzene moiety
  • Pyridine
  • Imidolactam
  • Benzenoid
  • Pyrrolidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Amino acid
  • Amino acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organofluoride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.07 g/LNot Available
LogP3.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.07 g/LALOGPS
logP0.86ALOGPS
logP0.14ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)5.41ChemAxon
pKa (Strongest Basic)9.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity101.04 m³·mol⁻¹ChemAxon
Polarizability38.34 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000b-2119000000-91742a1b93c82cf212d5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7003900000-4818baa2c2a4f74b2220View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0006900000-2710bf3a67a56277c91aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fyk-0009200000-09205f5639aced9d56b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2109000000-c9470417cb99415a7647View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gi0-0009300000-889348bd48600cb6c1a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0019000000-74abce38948c12f68820View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kdi-0269000000-576e128582edeb4bb363View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00685 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00685 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID56670
KEGG Compound IDC07664
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrovafloxacin
METLIN IDNot Available
PubChem Compound62959
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:
TOP2A
Uniprot ID:
P11388
Molecular weight:
174383.9
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]