Showing metabocard for Oxolinic Acid (BMDB0063613)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-10-03 16:33:30 UTC
Update Date2020-06-04 19:11:09 UTC
BMDB IDBMDB0063613
Secondary Accession Numbers
  • BMDB63613
Metabolite Identification
Common NameOxolinic Acid
DescriptionOxolinic acid is a quinolinemonocarboxylic acid having the carboxy group at position 7 as well as oxo and ethyl groups at positions 4 and 1 respectively and a dioxolo ring fused at the 5- and 6-positions. A synthetic antibiotic, it is used in veterinary medicine for the treatment of bacterial infections in cattle, pigs and poultry. It has a role as an antiinfective agent, an antibacterial drug, an enzyme inhibitor, an antimicrobial agent and an antifungal agent. It is a quinolinemonocarboxylic acid, an organic heterotricyclic compound, an aromatic carboxylic acid, an oxacycle and a quinolone antibiotic. It is a conjugate acid of an oxolinate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylic acidChEBI
1-Ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylic acidChEBI
5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)quinoline-7-carboxylic acidChEBI
Acide oxoliniqueChEBI
Acido oxolinicoChEBI
Acidum oxolinicumChEBI
OAChEBI
AqualinicKegg
1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylateGenerator
1-Ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylateGenerator
5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)quinoline-7-carboxylateGenerator
OxolinateGenerator
Acid, oxolinicMeSH
GramurinMeSH
Oxolinate, sodiumMeSH
Sodium oxolinateMeSH
Chemical FormulaC13H11NO5
Average Molecular Weight261.2301
Monoisotopic Molecular Weight261.063722467
IUPAC Name5-ethyl-8-oxo-2H,5H,8H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
Traditional Nameossian
CAS Registry Number14698-29-4
SMILES
CCN1C=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12
InChI Identifier
InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)
InChI KeyKYGZCKSPAKDVKC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinoline carboxylic acids
Direct ParentQuinoline carboxylic acids
Alternative Parents
Substituents
  • Quinoline-3-carboxylic acid
  • Dihydroquinolone
  • Dihydroquinoline
  • Benzodioxole
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Pyridine
  • Benzenoid
  • Vinylogous amide
  • Heteroaromatic compound
  • Acetal
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Azacycle
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.86ALOGPS
logP1.35ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)5.58ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.84 m³·mol⁻¹ChemAxon
Polarizability25.52 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-00l6-0490000000-237ab4e22ca8c87c87f9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0090000000-42a1a31f158e9bef1a7dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0790000000-0196f4b3fe02d848ac04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0920000000-8df3687ee0c2e91f987fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0090000000-24298432855bfc523660View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0090000000-0511184317d1b6d18d3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0090000000-95faf056ba91e8007c9bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03dl-0290000000-db6274d8128c051d14b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03e9-0960000000-c51deba0c41087d2cab2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03e9-0910000000-bb9589ba074c27740963View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0ho0-4900000000-a825bf27d8d3c0aee71fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-02di-9500000000-bccf49f73f4aeba1dfa3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-9100000000-55f0b933bb95b8ac1a52View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-03e9-0910000000-3c81458019c3bf0c9692View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-03e9-0960000000-f0f7c0d17b8af04334ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-03dl-0290000000-bf8142d91cf36f4709f4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-0090000000-0511184317d1b6d18d3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-03di-0090000000-9000f1dd05ac3d9ad631View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-03di-0920000000-741ae3bcdfd5e8398bf6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-0790000000-a21c32a280f959c2466bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-37dc156faa14512ceaabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0296-0090000000-4381353df0b7e7aeee1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0wtc-0790000000-e290c90d551c56e1ef77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02t9-0090000000-8aae635e5bdea056ef12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0590000000-4a91cc6c672c3b18ada6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-0920000000-cd83ad14bff62acfdf66View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified0.0356 - 0.0582 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0255996
DrugBank IDDB13627
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4467
KEGG Compound IDC11342
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxolinic_acid
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID138856
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chen D, Yu J, Tao Y, Pan Y, Xie S, Huang L, Peng D, Wang X, Wang Y, Liu Z, Yuan Z: Qualitative screening of veterinary anti-microbial agents in tissues, milk, and eggs of food-producing animals using liquid chromatography coupled with tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Apr 1;1017-1018:82-88. doi: 10.1016/j.jchromb.2016.02.037. Epub 2016 Mar 3. [PubMed:26950031 ]