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Showing metabocard for Clavulanate (HMDB0014904)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2019-01-11 19:34:34 UTC
HMDB IDHMDB0014904
Secondary Accession Numbers
  • HMDB14904
Metabolite Identification
Common NameClavulanate
DescriptionClavulanic acid and its salts and esters. The acid is a suicide inhibitor of bacterial beta-lactamase enzymes from Streptomyces clavuligerus. Administered alone, it has only weak antibacterial activity against most organisms, but given in combination with beta-lactam antibiotics prevents antibiotic inactivation by microbial lactamase. [PubChem].
Structure
Data?1547235274
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
(2R,3Z,5R)-3-(2-HYDROXYETHYLIDENE)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
Clavulanic acidGenerator
(Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylateGenerator
ClavulonateGenerator
Clavulanate potassiumMeSH
Clavulanic acid, monopotassium saltMeSH
Clavulanic acid, monosodium saltMeSH
Potassium clavulanateMeSH
Potassium, clavulanateMeSH
Clavulanate, potassiumMeSH
Clavulanate, sodiumMeSH
Sodium clavulanateMeSH
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
DescriptionThis compound 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9600000000-6fdd26b47c56a74e9833View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fdo-9332000000-43d295827ceaa5d9eb8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-1950000000-d5686d38b594be5d2075View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0910000000-f0aa4be27dc58b289a46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-c2baab863dddf5c7700cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-2900000000-8ae04a4401d4027a239fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-3900000000-d2ecee5934bb69d2c571View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-5900000000-f87d4c4d0c435b47a1a1View in MoNA
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available