Ertapenem (CED0002587)

Record Information

Version

1.0

Creation Date

2016-05-25 18:19:36 UTC

Update Date

2026-08-21 22:21:46 UTC

Accession Number

CHEM022086

Identification

Common Name

Ertapenem

Class

Small Molecule

Description

Ertapenem is an organic compound with the chemical formula C22H25N3O7S and an average molecular weight of 475.51 g/mol. Ertapenem belongs to the beta lactams, a subclass of lactams within the organic compounds. It is further categorized under the superclass of organoheterocyclic compounds. The compound is found in or released from seven recorded sources. These include healthcare, pharmaceuticals and veterinary products specifically as beta-lactam antibacterials, as well as food, food processing and cookware involving the processing of meats. Additionally, it is associated with household cleaning and consumer products, including other smoking requisites and non electric simulated smoking devices, and electrical and electronic equipment such as television systems, video games, superconducting coils, and superconducting magnets. Recorded routes of exposure for the compound include intravenous and intramuscular administration. Ertapenem acts on six recorded protein targets. It functions as an inhibitor of Penicillin-binding protein 1A (mrcA), Peptidoglycan D,D-transpeptidase FtsI (ftsI), Peptidoglycan D,D-transpeptidase MrdA (mrdA), and D-alanyl-D-alanine carboxypeptidase DacC (dacC), along with two other proteins.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1R,5S,6S,8R,2's,4's)-2-(2-(3-Carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid	ChEBI
(4R,5S,6S)-3-((3S,5S)-5-((3-Carboxyphenyl)carbamoyl)pyrrolidin-3-ylthio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid	ChEBI
Invanz	Kegg
(1R,5S,6S,8R,2's,4's)-2-(2-(3-Carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylate	Generator
(4R,5S,6S)-3-((3S,5S)-5-((3-Carboxyphenyl)carbamoyl)pyrrolidin-3-ylthio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate	Generator
Invanoz	HMDB
Ertapenem sodium	HMDB

Chemical Formula

C₂₂H₂₅N₃O₇S

Average Molecular Mass

475.515 g/mol

Monoisotopic Mass

475.141 g/mol

CAS Registry Number

153832-46-3

IUPAC Name

(4R,5S,6S)-3-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Traditional Name

ertapenem

SMILES

[H][C@]12[C@@H](C)C(S[C@]3([H])CN[C@@]([H])(C3)C(=O)NC3=CC=CC(=C3)C(O)=O)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(O)=O

InChI Identifier

InChI=1S/C22H25N3O7S/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32)/t9-,10-,13+,14+,15-,16-/m1/s1

InChI Key

JUZNIMUFDBIJCM-ANEDZVCMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Thienamycins

Alternative Parents

Substituents

Thienamycin
Acylaminobenzoic acid or derivatives
Proline or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Benzoic acid or derivatives
Benzoic acid
Anilide
Benzoyl
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
Pyrroline carboxylic acid
Pyrroline carboxylic acid or derivatives
N-arylamide
Azepine
Vinylogous thioester
Benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Tertiary carboxylic acid amide
Pyrroline
Pyrrolidine
Amino acid
Thioenolether
Secondary carboxylic acid amide
Secondary alcohol
Amino acid or derivatives
Azetidine
Carboxamide group
Azacycle
Secondary amine
Sulfenyl compound
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Alcohol
Organic oxide
Organopnictogen compound
Organosulfur compound
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Organooxygen compound
Amine
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyrrolidinecarboxamide (CHEBI:404903 )
carbapenemcarboxylic acid (CHEBI:404903 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.29 g/L	ALOGPS
logP	-0.2	ALOGPS
logP	-3.2	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	9.03	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	156.27 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	121.8 m³·mol⁻¹	ChemAxon
Polarizability	48.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-052s-9534600000-4519573496014739b64d	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-004i-1330109000-3e4c64387677650a4868	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-08fr-0671900000-9c71265b6eb31d52d925	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0btc-2594700000-77fee4b13a6be5eda787	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0i03-7940000000-5180d6afb461bc02edcc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0112900000-eb2b3b9bec00b61e40d8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-9522100000-19d44a1137bf99ec22b4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000b-0910000000-bfbef538a800a2a9369a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0000900000-67f3080f19375e1e5b65	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01x0-2669800000-1a104b6137295f16315b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-9551700000-d98a80ce480eb11e6736	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0000900000-0ac8f3f9ea1bb5092d3a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-06vi-0242900000-80846507b55d0a05e004	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0v5c-1910100000-22f085e058edecc88ecd	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
3058.0	Log mg/kg	[1700:5400]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
341	Beta-lactam antibacterials	Healthcare, pharmaceuticals & veterinary products	Not Available
535	Superconducting Magnets And Superconducting Coils	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
552	Processing Meats	Food, food processing & cookware	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available

Pathways

1 pathway

Ertapenem Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Beta-lactamase OXA-48	Q6XEC0	Klebsiella pneumoniae	Predicted (SEA)	0.0778492
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	112.336
Click to view 3D structure	Polymerase acidic protein	Q9QLI9	Influenza B virus (strain B/Lee/1940)	Predicted (SEA)	5.0602
Click to view 3D structure	S-sulfocysteine synthase	Q79FV4	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Predicted (SEA)	29.7384
Click to view 3D structure	O-phosphoserine sulfhydrylase	P9WP53	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Predicted (SEA)	30.1276
Click to view 3D structure	Gastrin/cholecystokinin type B receptor	P30553	Rattus norvegicus	Predicted (SEA)	203.809
Click to view 3D structure	O-acetylserine sulfhydrylase	P9WP55	Mycobacterium tuberculosis	Predicted (SEA)	15.5698
Click to view 3D structure	Gastrin/cholecystokinin type B receptor	P56481	Mus musculus	Predicted (SEA)	234.793
Click to view 3D structure	Poly [ADP-ribose] polymerase 1	P09874	Humans	Predicted (SEA)	495.043
Click to view 3D structure	Gastrin/cholecystokinin type B receptor	P32239	Humans	Predicted (SEA)	435.8
Click to view 3D structure	Cholecystokinin receptor type A	Q63931	Cavia porcellus	Predicted (SEA)	256.435
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 7	P35236	Humans	Predicted (SEA)	619.446
Click to view 3D structure	Cholecystokinin receptor type A	P32238	Humans	Predicted (SEA)	363.167
Click to view 3D structure	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820	Humans	Predicted (SEA)	1351.85
Click to view 3D structure	Gastrin/cholecystokinin type B receptor	P30552	Canis lupus familiaris	Predicted (SEA)	11.9888
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	5765.82
Click to view 3D structure	Protein mono-ADP-ribosyltransferase PARP14	Q460N5	Humans	Predicted (SEA)	246.782
Click to view 3D structure	Potassium channel subfamily K member 3	O14649	Humans	Predicted (SEA)	331.716
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	5905.17
Click to view 3D structure	Peroxisome proliferator-activated receptor alpha	Q07869	Humans	Predicted (SEA)	1216.55
Click to view 3D structure	Protein mono-ADP-ribosyltransferase PARP15	Q460N3	Humans	Predicted (SEA)	196.414
Click to view 3D structure	Apoptotic protease-activating factor 1	O14727	Humans	Predicted (SEA)	603.954
Click to view 3D structure	Prothrombin	P00734	Humans	Predicted (SEA)	2397.13
Click to view 3D structure	Heat shock protein HSP 90-alpha	P07900	Humans	Predicted (SEA)	735.597
Click to view 3D structure	Hexokinase HKDC1	Q2TB90	Humans	Predicted (SEA)	396.097