Human Metabolome Database: Showing metabocard for Clavulanate (HMDB0014904)

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Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2020-02-26 21:40:33 UTC

HMDB ID

HMDB0014904

Secondary Accession Numbers

HMDB14904

Metabolite Identification

Common Name

Clavulanate

Description

Clavulanate, 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R,3Z,5R)-3-(2-HYDROXYETHYLIDENE)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylIC ACID	ChEBI
(Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid	ChEBI
Acide clavulanique	ChEBI
Acido clavulanico	ChEBI
Acidum clavulanicum	ChEBI
Antibiotic MM 14151	ChEBI
Clavulansaeure	ChEBI
Clavulonic acid	ChEBI
MM 14151	ChEBI
CVA	Kegg
Clavulox	Kegg
(2R,3Z,5R)-3-(2-HYDROXYETHYLIDENE)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
(Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylate	Generator
Clavulonate	Generator
Clavulanic acid	Generator
Clavulanate potassium	HMDB
Clavulanic acid, monopotassium salt	HMDB
Clavulanic acid, monosodium salt	HMDB
Potassium clavulanate	HMDB
Potassium, clavulanate	HMDB
Clavulanate, potassium	HMDB
Clavulanate, sodium	HMDB
Sodium clavulanate	HMDB
Clavulanate	ChEBI

Chemical Formula

C₈H₉NO₅

Average Molecular Weight

199.1608

Monoisotopic Molecular Weight

199.048072403

IUPAC Name

(2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

clavulanate

CAS Registry Number

58001-44-8

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 Key

HZZVJAQRINQKSD-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha 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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

oxapenam (CHEBI:48947 )
Clavams (C06662 )

Ontology

Disposition

Route of exposure:

Parenteral:

Dermal

Biological location:

Biofluid and excreta:

Role

Indirect biological role:

Biological role:

Industrial application:

Enzyme inhibitor:

Food and nutrition:

Household products:

Antifungal

Pesticide:

Antimicrobial agent:

Pharmaceutical industry:

Antineoplastic agent:

Neuromuscular agent:

Cardiovascular drug:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	117.5 - 118 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	337 g/L	Not Available
LogP	-1.5	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	337 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.5	ChemAxon
logS	0.23	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.25 m³·mol⁻¹	ChemAxon
Polarizability	18.13 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9600000000-6fdd26b47c56a74e9833	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0fdo-9332000000-43d295827ceaa5d9eb8a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-1950000000-d5686d38b594be5d2075	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-0910000000-f0aa4be27dc58b289a46	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-c2baab863dddf5c7700c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udj-2900000000-8ae04a4401d4027a239f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fk9-3900000000-d2ecee5934bb69d2c571	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-5900000000-f87d4c4d0c435b47a1a1	Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00766	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00766	21059682	details