Piromidic acid (CHEM018311)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:08:57 UTC
Update Date2016-11-09 01:15:46 UTC
Accession NumberCHEM018311
Identification
Common NamePiromidic acid
ClassSmall Molecule
DescriptionA pyridopyrimidine that is 5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid, substituted at position 2 by a pyrrolidin-1-yl group and at position 8 by an ethyl group. A synthetic antibacterial which is used for the treatment of urinary tract and intestinal infections.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
8-Ethyl-5,8-dihydro-5-oxo-2-(1-pyrrolidinyl)pyrido(2,3-D)pyrimidine-6-carboxylic acidChEBI
Acide piromidiqueChEBI
Acido piromidicoChEBI
Acidum piromidicumChEBI
Actrun CChEBI
BactramylChEBI
EnterolChEBI
GastrurolChEBI
PanacidChEBI
Pyromidic acidChEBI
ReelonChEBI
SepturalChEBI
UropirChEBI
8-Ethyl-5,8-dihydro-5-oxo-2-(1-pyrrolidinyl)pyrido(2,3-D)pyrimidine-6-carboxylateGenerator
PyromidateGenerator
PiromidateGenerator
PAKEGG
Acid, piromidicMeSH
Chemical FormulaC14H16N4O3
Average Molecular Mass288.307 g/mol
Monoisotopic Mass288.122 g/mol
CAS Registry Number19562-30-2
IUPAC Name8-ethyl-5-oxo-2-(pyrrolidin-1-yl)-5H,8H-pyrido[2,3-d]pyrimidine-6-carboxylic acid
Traditional Nameenterol
SMILESCCN1C=C(C(O)=O)C(=O)C2=CN=C(N=C12)N1CCCC1
InChI IdentifierInChI=1S/C14H16N4O3/c1-2-17-8-10(13(20)21)11(19)9-7-15-14(16-12(9)17)18-5-3-4-6-18/h7-8H,2-6H2,1H3,(H,20,21)
InChI KeyRCIMBBZXSXFZBV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrido[2,3-d]pyrimidines. Pyrido[2,3-d]pyrimidines are compounds containing the pyrido[2,3-d]pyrimidine ring system, which is a pyridopyrimidine isomer with three ring nitrogen atoms at the 1-, 3-, and 8- position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridopyrimidines
Sub ClassPyrido[2,3-d]pyrimidines
Direct ParentPyrido[2,3-d]pyrimidines
Alternative Parents
Substituents
  • Pyrido[2,3-d]pyrimidine
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Dialkylarylamine
  • Aminopyrimidine
  • Pyrimidine
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Pyrrolidine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility1.21 g/LALOGPS
logP0.42ALOGPS
logP1.59ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)5.61ChemAxon
pKa (Strongest Basic)3.03ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity78.97 m³·mol⁻¹ChemAxon
Polarizability29.78 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, Positivesplash10-006x-0980000000-e0572e12c19b3c4fdc72Spectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-6dac86f0218e62a678daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dv-0090000000-1c0f05e8b35af7223253Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-6790000000-78a7c8439d721f499128Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-0090000000-dc4762fae5c89796d99aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014l-0090000000-69c6b20abe5c1bb4e3e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02ta-4490000000-8348d7b2352fe3679cbfSpectrum
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 IDDB13744
HMDB IDHMDB0256609
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPiromidic_acid
Chemspider ID4689
ChEBI ID32019
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1021250
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1274382
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=3227506
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=346547
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=4939730
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=526354
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=535334
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=5535400
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=589722
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=6222321
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=670126
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=772246
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=975416
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=975418