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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2021-09-14 15:19:49 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. Clavulanate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Clavulanate.
Structure
Data?1582753233
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
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 potassiumMeSH, HMDB
Clavulanic acid, monopotassium saltMeSH, HMDB
Clavulanic acid, monosodium saltMeSH, HMDB
Potassium clavulanateMeSH, HMDB
Potassium, clavulanateMeSH, HMDB
Clavulanate, potassiumMeSH, HMDB
Clavulanate, sodiumMeSH, HMDB
Sodium clavulanateMeSH, HMDB
ClavulanateChEBI
CVAKEGG
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point117.5 - 118 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility337 g/LNot Available
LogP-1.5Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility337 g/LALOGPS
logP10(-1.2) g/LALOGPS
logP10(-1.5) g/LChemAxon
logS10(0.23) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+143.97931661259
DarkChem[M-H]-138.51631661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Clavulanate[H][C@@]12CC(=O)N1[C@@H](C(O)=O)\C(O2)=C\CO3224.5Standard polar33892256
Clavulanate[H][C@@]12CC(=O)N1[C@@H](C(O)=O)\C(O2)=C\CO1849.7Standard non polar33892256
Clavulanate[H][C@@]12CC(=O)N1[C@@H](C(O)=O)\C(O2)=C\CO1901.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Clavulanate,1TMS,isomer #1C[Si](C)(C)OC(=O)[C@H]1/C(=C/CO)O[C@@H]2CC(=O)N211868.8Semi standard non polar33892256
Clavulanate,1TMS,isomer #2C[Si](C)(C)OC/C=C1\O[C@@H]2CC(=O)N2[C@H]1C(=O)O1914.2Semi standard non polar33892256
Clavulanate,2TMS,isomer #1C[Si](C)(C)OC/C=C1\O[C@@H]2CC(=O)N2[C@H]1C(=O)O[Si](C)(C)C1935.8Semi standard non polar33892256
Clavulanate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H]1/C(=C/CO)O[C@@H]2CC(=O)N212097.6Semi standard non polar33892256
Clavulanate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC/C=C1\O[C@@H]2CC(=O)N2[C@H]1C(=O)O2153.5Semi standard non polar33892256
Clavulanate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC/C=C1\O[C@@H]2CC(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C2370.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Clavulanate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9600000000-6fdd26b47c56a74e98332017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clavulanate GC-MS (2 TMS) - 70eV, Positivesplash10-0fdo-9332000000-43d295827ceaa5d9eb8a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clavulanate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clavulanate 10V, Positive-QTOFsplash10-0f89-1950000000-d5686d38b594be5d20752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clavulanate 20V, Positive-QTOFsplash10-0f89-0910000000-f0aa4be27dc58b289a462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clavulanate 40V, Positive-QTOFsplash10-00di-9000000000-c2baab863dddf5c7700c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clavulanate 10V, Negative-QTOFsplash10-0udj-2900000000-8ae04a4401d4027a239f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clavulanate 20V, Negative-QTOFsplash10-0fk9-3900000000-d2ecee5934bb69d2c5712016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clavulanate 40V, Negative-QTOFsplash10-03di-5900000000-f87d4c4d0c435b47a1a12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clavulanate 10V, Positive-QTOFsplash10-0udi-0390000000-daf29ac93fc88782f4e22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clavulanate 20V, Positive-QTOFsplash10-0umr-2900000000-b620a2bdca14749389272021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clavulanate 40V, Positive-QTOFsplash10-006x-9700000000-12eecdbc970384d5c4e12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clavulanate 10V, Negative-QTOFsplash10-0uka-0900000000-9a7387dd008ab82f80392021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clavulanate 20V, Negative-QTOFsplash10-01w0-2900000000-32e74f2ada87a1118cad2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clavulanate 40V, Negative-QTOFsplash10-0006-9400000000-ff80ae29ba99ef876d412021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00766 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB 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
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available