Biapenem (CED0008373)

Record Information

Version

1.0

Creation Date

2016-05-22 05:44:30 UTC

Update Date

2026-05-14 19:28:54 UTC

Accession Number

CHEM018991

Identification

Common Name

Biapenem

Class

Small Molecule

Description

Biapenem is an organic compound with the chemical formula C15H18N4O4S and an average molecular weight of 350.39 g/mol. Biapenem belongs to the beta lactams, a subclass of lactams within the organic compounds. It is further classified within the superclass of organoheterocyclic compounds. The compound is identified in five recorded sources, which include antibiotics within healthcare, pharmaceuticals, and veterinary products, as well as electrical and electronic equipment such as communication cables or conductors, radio transmission systems, line transmission systems, and antennas. Recorded routes of exposure for this substance include oral and inhalation. In terms of biological activity, biapenem interacts with seven recorded protein targets. It acts as an inhibitor of penicillin-binding protein 1A (mrcA), penicillin-binding protein 1B (mrcB), D-alanyl-D-alanine carboxypeptidase DacC (dacC), and peptidoglycan D,D-transpeptidase MrdA (mrdA), in addition to three other proteins.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Omegacin	Kegg
3-((6,7-Dihydro-5H-pyrazolo(1,2-a)(1,2,4)triazol-4-ium-6-yl)thio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3,2,0)hept-2-ene-2-carboxylate	MeSH
(4R,5S,6S)-3-(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]Triazol-4-ium-6-ylthio)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	ChEBI
(4R,5S,6S)-3-(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]Triazol-4-ium-6-ylthio)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid	Generator
(4R,5S,6S)-3-(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]Triazol-4-ium-6-ylsulfanyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid	Generator
(4R,5S,6S)-3-(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]Triazol-4-ium-6-ylsulphanyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	Generator
(4R,5S,6S)-3-(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]Triazol-4-ium-6-ylsulphanyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid	Generator
Biapenem	MeSH
BIPM	ChEBI

Chemical Formula

C₁₅H₁₈N₄O₄S

Average Molecular Mass

350.390 g/mol

Monoisotopic Mass

350.105 g/mol

CAS Registry Number

120410-24-4

IUPAC Name

6-{[(4R,5S,6S)-2-carboxylato-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]sulfanyl}-5H,6H,7H-4λ⁵-pyrazolo[1,2-a][1,2,4]triazol-4-ylium

Traditional Name

biapenem

SMILES

[H][C@](C)(O)[C@@]1([H])C(=O)N2C(C([O-])=O)=C(SC3CN4C=NC=[N+]4C3)[C@]([H])(C)[C@]12[H]

InChI Identifier

InChI=1S/C15H18N4O4S/c1-7-11-10(8(2)20)14(21)19(11)12(15(22)23)13(7)24-9-3-17-5-16-6-18(17)4-9/h5-11,20H,3-4H2,1-2H3/t7-,8-,10-,11-/m1/s1

InChI Key

MRMBZHPJVKCOMA-YJFSRANCSA-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
Alpha-amino acid or derivatives
Pyrroline carboxylic acid
Pyrroline carboxylic acid or derivatives
Azepine
Vinylogous thioester
Azole
Heteroaromatic compound
Pyrroline
1,2,4-triazole
Tertiary carboxylic acid amide
Azetidine
Carboxamide group
Carboxylic acid salt
Thioenolether
Secondary alcohol
Carboxylic acid derivative
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Sulfenyl compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Organosulfur compound
Organic salt
Organic zwitterion
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic sulfide (CHEBI:3089 )
carbapenems (CHEBI:3089 )
pyrazolotriazole (CHEBI:3089 )

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	2.75 g/L	ALOGPS
logP	-2	ALOGPS
logP	-6.1	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.51	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	102.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	120.82 m³·mol⁻¹	ChemAxon
Polarizability	35.06 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	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0109000000-3dbdc56f6a48a27b0191	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01ox-4908000000-6d2221a7edbb6dba8a3a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03dm-4900000000-dae623104f4609bd727e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-1009000000-ca88238d11b4951e03e0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-9200000000-243cade4c45f0a406f4e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00mo-7900000000-3e618cdcb0eff181f6e0	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
8764.0	Log mg/kg	[4900:16000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
306	Antibiotics	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
510	Communication Cables Or Conductors	Electrical & Electronic Equipment	Not Available
525	Line Transmission Systems	Electrical & Electronic Equipment	Not Available
530	Radio Transmission Systems	Electrical & Electronic Equipment	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Sorbitol dehydrogenase	P27867	Rattus norvegicus	Predicted (SEA)	302.444
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	7654.84
Click to view 3D structure	Beta-lactamase	P00807	Staphylococcus aureus	Predicted (SEA)	25.5345
Click to view 3D structure	Rho-associated protein kinase 2	O75116	Humans	Predicted (SEA)	7602.37
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	7528.8
Click to view 3D structure	Synaptic vesicle glycoprotein 2A	Q02563	Rattus norvegicus	Predicted (SEA)	139.039
Click to view 3D structure	Beta-lactamase	P00808	Bacillus licheniformis	Predicted (SEA)	25.6124
Click to view 3D structure	C-C chemokine receptor type 5	P51681	Humans	Predicted (SEA)	6092.87
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	7588.74
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	7672.74
Click to view 3D structure	Prostaglandin E2 receptor EP2 subtype	P43116	Humans	Predicted (SEA)	6192.91
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	7716.73
Click to view 3D structure	Peptidoglycan D,D-transpeptidase MrdA	P0AD65	Escherichia coli (strain K12)	Predicted (SEA)	16.9711
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)	3618.51
Click to view 3D structure	Beta-lactamase class C	Q59401	Enterobacter cloacae	Predicted (SEA)	21.4085
Click to view 3D structure	Beta-lactamase	P05364	Enterobacter cloacae	Predicted (SEA)	35.3435
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	7655.77
Click to view 3D structure	Beta-lactamase TEM	P62593	Escherichia coli	Predicted (SEA)	83.4544
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	7684.65
Click to view 3D structure	Beta-lactamase	P00811	Escherichia coli (strain K12)	Predicted (SEA)	1084.98
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	7736.81
Click to view 3D structure	Beta-lactamase	P24735	Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)	Predicted (SEA)	162.938
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	7716.8
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	7544.6