Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:45 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 It was withdrawn from the market due to the risk of hepatotoxicity.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
Data?1582753224
Synonyms
ValueSource
TVFXHMDB
7-[(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-carboxylateHMDB
TrovafloxacinMeSH
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
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
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.07 g/LNot Available
LogP3.7Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
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]-229.30330932474
DeepCCS[M+Na]+204.72630932474
AllCCS[M+H]+191.232859911
AllCCS[M+H-H2O]+188.732859911
AllCCS[M+NH4]+193.432859911
AllCCS[M+Na]+194.132859911
AllCCS[M-H]-190.532859911
AllCCS[M+Na-2H]-190.032859911
AllCCS[M+HCOO]-189.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Trovafloxacin[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)=O4049.7Standard polar33892256
Trovafloxacin[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)=O2786.2Standard non polar33892256
Trovafloxacin[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)=O3629.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Trovafloxacin,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CN(C2=CC=C(F)C=C2F)C2=NC(N3C[C@H]4C(N)[C@H]4C3)=C(F)C=C2C1=O3292.8Semi standard non polar33892256
Trovafloxacin,1TMS,isomer #2C[Si](C)(C)NC1[C@@H]2CN(C3=NC4=C(C=C3F)C(=O)C(C(=O)O)=CN4C3=CC=C(F)C=C3F)C[C@H]123363.5Semi standard non polar33892256
Trovafloxacin,2TMS,isomer #1C[Si](C)(C)NC1[C@@H]2CN(C3=NC4=C(C=C3F)C(=O)C(C(=O)O[Si](C)(C)C)=CN4C3=CC=C(F)C=C3F)C[C@H]123282.5Semi standard non polar33892256
Trovafloxacin,2TMS,isomer #1C[Si](C)(C)NC1[C@@H]2CN(C3=NC4=C(C=C3F)C(=O)C(C(=O)O[Si](C)(C)C)=CN4C3=CC=C(F)C=C3F)C[C@H]123343.5Standard non polar33892256
Trovafloxacin,2TMS,isomer #1C[Si](C)(C)NC1[C@@H]2CN(C3=NC4=C(C=C3F)C(=O)C(C(=O)O[Si](C)(C)C)=CN4C3=CC=C(F)C=C3F)C[C@H]123997.8Standard polar33892256
Trovafloxacin,2TMS,isomer #2C[Si](C)(C)N(C1[C@@H]2CN(C3=NC4=C(C=C3F)C(=O)C(C(=O)O)=CN4C3=CC=C(F)C=C3F)C[C@H]12)[Si](C)(C)C3344.2Semi standard non polar33892256
Trovafloxacin,2TMS,isomer #2C[Si](C)(C)N(C1[C@@H]2CN(C3=NC4=C(C=C3F)C(=O)C(C(=O)O)=CN4C3=CC=C(F)C=C3F)C[C@H]12)[Si](C)(C)C3394.0Standard non polar33892256
Trovafloxacin,2TMS,isomer #2C[Si](C)(C)N(C1[C@@H]2CN(C3=NC4=C(C=C3F)C(=O)C(C(=O)O)=CN4C3=CC=C(F)C=C3F)C[C@H]12)[Si](C)(C)C4102.5Standard polar33892256
Trovafloxacin,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CN(C2=CC=C(F)C=C2F)C2=NC(N3C[C@H]4C(N([Si](C)(C)C)[Si](C)(C)C)[C@H]4C3)=C(F)C=C2C1=O3313.9Semi standard non polar33892256
Trovafloxacin,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CN(C2=CC=C(F)C=C2F)C2=NC(N3C[C@H]4C(N([Si](C)(C)C)[Si](C)(C)C)[C@H]4C3)=C(F)C=C2C1=O3442.3Standard non polar33892256
Trovafloxacin,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CN(C2=CC=C(F)C=C2F)C2=NC(N3C[C@H]4C(N([Si](C)(C)C)[Si](C)(C)C)[C@H]4C3)=C(F)C=C2C1=O3831.1Standard polar33892256
Trovafloxacin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CN(C2=CC=C(F)C=C2F)C2=NC(N3C[C@H]4C(N)[C@H]4C3)=C(F)C=C2C1=O3497.4Semi standard non polar33892256
Trovafloxacin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1[C@@H]2CN(C3=NC4=C(C=C3F)C(=O)C(C(=O)O)=CN4C3=CC=C(F)C=C3F)C[C@H]123560.8Semi standard non polar33892256
Trovafloxacin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1[C@@H]2CN(C3=NC4=C(C=C3F)C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN4C3=CC=C(F)C=C3F)C[C@H]123643.3Semi standard non polar33892256
Trovafloxacin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1[C@@H]2CN(C3=NC4=C(C=C3F)C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN4C3=CC=C(F)C=C3F)C[C@H]123762.7Standard non polar33892256
Trovafloxacin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1[C@@H]2CN(C3=NC4=C(C=C3F)C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN4C3=CC=C(F)C=C3F)C[C@H]124145.2Standard polar33892256
Trovafloxacin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1[C@@H]2CN(C3=NC4=C(C=C3F)C(=O)C(C(=O)O)=CN4C3=CC=C(F)C=C3F)C[C@H]12)[Si](C)(C)C(C)(C)C3803.4Semi standard non polar33892256
Trovafloxacin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1[C@@H]2CN(C3=NC4=C(C=C3F)C(=O)C(C(=O)O)=CN4C3=CC=C(F)C=C3F)C[C@H]12)[Si](C)(C)C(C)(C)C3812.3Standard non polar33892256
Trovafloxacin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1[C@@H]2CN(C3=NC4=C(C=C3F)C(=O)C(C(=O)O)=CN4C3=CC=C(F)C=C3F)C[C@H]12)[Si](C)(C)C(C)(C)C4167.2Standard polar33892256
Trovafloxacin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CN(C2=CC=C(F)C=C2F)C2=NC(N3C[C@H]4C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]4C3)=C(F)C=C2C1=O3885.1Semi standard non polar33892256
Trovafloxacin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CN(C2=CC=C(F)C=C2F)C2=NC(N3C[C@H]4C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]4C3)=C(F)C=C2C1=O4044.1Standard non polar33892256
Trovafloxacin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CN(C2=CC=C(F)C=C2F)C2=NC(N3C[C@H]4C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]4C3)=C(F)C=C2C1=O4006.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Trovafloxacin GC-MS (Non-derivatized) - 70eV, Positivesplash10-000b-2119000000-91742a1b93c82cf212d52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trovafloxacin GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7003900000-4818baa2c2a4f74b22202017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trovafloxacin 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 - Trovafloxacin 10V, Positive-QTOFsplash10-0gb9-0006900000-2710bf3a67a56277c91a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trovafloxacin 20V, Positive-QTOFsplash10-0fyk-0009200000-09205f5639aced9d56b12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trovafloxacin 40V, Positive-QTOFsplash10-0udi-2109000000-c9470417cb99415a76472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trovafloxacin 10V, Negative-QTOFsplash10-0gi0-0009300000-889348bd48600cb6c1a52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trovafloxacin 20V, Negative-QTOFsplash10-0fk9-0019000000-74abce38948c12f688202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trovafloxacin 40V, Negative-QTOFsplash10-0kdi-0269000000-576e128582edeb4bb3632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trovafloxacin 10V, Positive-QTOFsplash10-014i-0000900000-3867ec761451154ce3c82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trovafloxacin 20V, Positive-QTOFsplash10-0002-0009000000-73e5733bc87ce9b57a252021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trovafloxacin 40V, Positive-QTOFsplash10-0v7j-0019000000-0c5ac23c528b63c072a62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trovafloxacin 10V, Negative-QTOFsplash10-0gb9-0008900000-f2e46d3c5f677f4673992021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trovafloxacin 20V, Negative-QTOFsplash10-0udi-0009000000-cecc830cc169437c18612021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trovafloxacin 40V, Negative-QTOFsplash10-0udi-0129000000-26a3bdcab7848d6041402021-10-11Wishart 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 DB00685 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB 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
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

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 ]