Showing metabocard for Oxolinic Acid (BMDB0063613)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-10-03 16:33:30 UTC
Update Date2020-06-04 19:11:09 UTC
MCDB ID BMDB0063613
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
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00l6-0490000000-237ab4e22ca8c87c87f92021-09-24View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0090000000-42a1a31f158e9bef1a7d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0790000000-0196f4b3fe02d848ac042017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0920000000-8df3687ee0c2e91f987f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0090000000-24298432855bfc5236602017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0090000000-0511184317d1b6d18d3f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0090000000-95faf056ba91e8007c9b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03dl-0290000000-db6274d8128c051d14b82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03e9-0960000000-c51deba0c41087d2cab22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03e9-0910000000-bb9589ba074c277409632017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0ho0-4900000000-a825bf27d8d3c0aee71f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-02di-9500000000-bccf49f73f4aeba1dfa32017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-9100000000-55f0b933bb95b8ac1a522017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-03e9-0910000000-3c81458019c3bf0c96922021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-03e9-0960000000-f0f7c0d17b8af04334ce2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-03dl-0290000000-bf8142d91cf36f4709f42021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-0090000000-0511184317d1b6d18d3f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-03di-0090000000-9000f1dd05ac3d9ad6312021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-03di-0920000000-741ae3bcdfd5e8398bf62021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-0790000000-a21c32a280f959c2466b2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-37dc156faa14512ceaab2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0296-0090000000-4381353df0b7e7aeee1d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0wtc-0790000000-e290c90d551c56e1ef772016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02t9-0090000000-8aae635e5bdea056ef122016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0590000000-4a91cc6c672c3b18ada62016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-0920000000-cd83ad14bff62acfdf662016-08-03View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.0356 - 0.0582 uM details
HMDB IDHMDB0255996
DrugBank IDDB13627
Phenol Explorer Compound IDNot Available
FoodDB 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 ]