Oxolinic acid (CHEM016380)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:29:38 UTC
Update Date2016-11-09 01:15:23 UTC
Accession NumberCHEM016380
Identification
Common NameOxolinic acid
ClassSmall Molecule
DescriptionA 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.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical 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 Mass261.230 g/mol
Monoisotopic Mass261.064 g/mol
CAS Registry Number14698-29-4
IUPAC Name5-ethyl-8-oxo-2H,5H,8H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
Traditional Nameossian
SMILESCCN1C=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.91 g/LALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00l6-0490000000-237ab4e22ca8c87c87f9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0090000000-42a1a31f158e9bef1a7dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0790000000-0196f4b3fe02d848ac04Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0920000000-8df3687ee0c2e91f987fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0090000000-24298432855bfc523660Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0090000000-0511184317d1b6d18d3fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0090000000-95faf056ba91e8007c9bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03dl-0290000000-db6274d8128c051d14b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03e9-0960000000-c51deba0c41087d2cab2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03e9-0910000000-bb9589ba074c27740963Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0ho0-4900000000-a825bf27d8d3c0aee71fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-02di-9500000000-bccf49f73f4aeba1dfa3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-9100000000-55f0b933bb95b8ac1a52Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-03e9-0910000000-3c81458019c3bf0c9692Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-03e9-0960000000-f0f7c0d17b8af04334ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-03dl-0290000000-bf8142d91cf36f4709f4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-0090000000-0511184317d1b6d18d3fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-03di-0090000000-9000f1dd05ac3d9ad631Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-03di-0920000000-741ae3bcdfd5e8398bf6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-0790000000-a21c32a280f959c2466bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-37dc156faa14512ceaabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0296-0090000000-4381353df0b7e7aeee1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0wtc-0790000000-e290c90d551c56e1ef77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02t9-0090000000-8aae635e5bdea056ef12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0590000000-4a91cc6c672c3b18ada6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-0920000000-cd83ad14bff62acfdf66Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB13627
HMDB IDHMDB0255996
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkOxolinic_acid
Chemspider ID4467
ChEBI ID138856
PubChem Compound IDNot Available
Kegg Compound IDC11342
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1245092
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1245092
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1650428
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19596082
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20151406
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22670590
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23353085
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23773949
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23816421
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=26678217
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=26920300
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=29438107
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=4616804