ChemFOnt: Showing chemical card for Clavulanate (CFc000009232)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:18 UTC

Chemfont ID

CFc000009232

Molecule Identification

Common Name

Clavulanate

Definition

Clavulanic 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

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
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	MeSH, HMDB
Clavulanic acid, monopotassium salt	MeSH, HMDB
Clavulanic acid, monosodium salt	MeSH, HMDB
Potassium clavulanate	MeSH, HMDB
Potassium, clavulanate	MeSH, HMDB
Clavulanate, potassium	MeSH, HMDB
Clavulanate, sodium	MeSH, HMDB
Sodium clavulanate	MeSH, HMDB
Clavulanate	ChEBI
CVA	KEGG

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 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0014904)

Source

Exogenous

Exogenous (HMDB: HMDB0014904)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Nutritional supplement

Enzyme replacement agent (HMDB: HMDB0014904)

Pharmaceutical industry

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Analgesic (HMDB: HMDB0014904)

Fluid processing agent

Surfactant

Surface-active agent (HMDB: HMDB0014904)

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0014904)

Combustive element

Explosive (HMDB: HMDB0014904)

Agriculture

Pesticide

Acaricide (HMDB: HMDB0014904)

Biological role

Metabolite (HMDB: HMDB0014904)

Modulator

Inhibitor

Enzyme inhibitor

Enzyme Inhibitor (HMDB: HMDB0014904)

Membrane transport modulator

Sodium chloride symporter inhibitor (HMDB: HMDB0014904)

Indirect biological role

Metabotoxin

Teratogen (HMDB: HMDB0014904)

Physical Properties

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