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Showing metabocard for Clavulanate (HMDB0014904)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:33 UTC
HMDB IDHMDB0014904
Secondary Accession Numbers
  • HMDB14904
Metabolite Identification
Common NameClavulanate
DescriptionClavulanate, also known as acido clavulanico or clavulansaeure, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Seizures may also occur in a case of overdose, or in a patient with renal failure. Clavulanate is an extremely weak basic (essentially neutral) compound (based on its pKa). Clavulanate has demonstrated low oral acute toxicity in adult rodents, having an LD50 of more than 2000 mg/kg. Gastrointestinal disturbance and mortality occurred, even at lower Clavulanate doses of 125 mg/kg. Offer symptomatic treatment or gastrointestinal disturbances, while considering the importance of fluid and electrolyte balance. When it is combined with amoxicillin, Clavulanate is frequently known as Augmentin, Co-Amoxiclav, or Clavulin. This helps to treat a variety of bacterial infections which would otherwise be resistant to antibiotics without the addition of clavulanic acid.
Structure
Data?1582753233
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R,3Z,5R)-3-(2-HYDROXYETHYLIDENE)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylIC ACIDChEBI
(Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acidChEBI
Acide clavulaniqueChEBI
Acido clavulanicoChEBI
Acidum clavulanicumChEBI
Antibiotic MM 14151ChEBI
ClavulansaeureChEBI
Clavulonic acidChEBI
MM 14151ChEBI
CVAKegg
ClavuloxKegg
(2R,3Z,5R)-3-(2-HYDROXYETHYLIDENE)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
(Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylateGenerator
ClavulonateGenerator
Clavulanic acidGenerator
Clavulanate potassiumHMDB
Clavulanic acid, monopotassium saltHMDB
Clavulanic acid, monosodium saltHMDB
Potassium clavulanateHMDB
Potassium, clavulanateHMDB
Clavulanate, potassiumHMDB
Clavulanate, sodiumHMDB
Sodium clavulanateHMDB
ClavulanateChEBI
Chemical FormulaC8H9NO5
Average Molecular Weight199.1608
Monoisotopic Molecular Weight199.048072403
IUPAC Name(2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Nameclavulanate
CAS Registry Number58001-44-8
SMILES
[H][C@@]12CC(=O)N1[C@@H](C(O)=O)\C(O2)=C\CO
InChI Identifier
InChI=1S/C8H9NO5/c10-2-1-4-7(8(12)13)9-5(11)3-6(9)14-4/h1,6-7,10H,2-3H2,(H,12,13)/b4-1-/t6-,7-/m1/s1
InChI KeyHZZVJAQRINQKSD-PBFISZAISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Clavam
  • Para-oxazepine
  • Beta-lactam
  • Tertiary carboxylic acid amide
  • Oxazolidine
  • Azetidine
  • Carboxamide group
  • Lactam
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Role

Indirect biological role:

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point117.5 - 118 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility337 g/LNot Available
LogP-1.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility337 g/LALOGPS
logP-1.2ALOGPS
logP-1.5ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.25 m³·mol⁻¹ChemAxon
Polarizability18.13 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9600000000-6fdd26b47c56a74e9833Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fdo-9332000000-43d295827ceaa5d9eb8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-1950000000-d5686d38b594be5d2075Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0910000000-f0aa4be27dc58b289a46Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-c2baab863dddf5c7700cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-2900000000-8ae04a4401d4027a239fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-3900000000-d2ecee5934bb69d2c571Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-5900000000-f87d4c4d0c435b47a1a1Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00766 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00766 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00766
Phenol Explorer Compound IDNot Available
FoodDB IDFDB009356
KNApSAcK IDC00018091
Chemspider ID4444466
KEGG Compound IDC06662
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkClavulanic_Acid
METLIN IDNot Available
PubChem Compound5280980
PDB IDJ01
ChEBI ID48947
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available