GRADE & PURITY Moligand™, 10mM in Water

Synonyms

NCGC00164551-01 | LJC 10627 | Tox21_112180 | (4R,5S,6S)-3-((6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | BIAPENEM [MI] | Cgp 57148 | LJ C10,627 | RPX2003

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Biapenem is a carbepenem that exhibits antibacterial activities against a wide range of gram-positive and gram-negative bacteria.
A carbepenem with antibacterial action

Specifications

Synonyms

NCGC00164551-01 | LJC 10627 | Tox21_112180 | (4R, 5S, 6S)-3-((6, 7-dihydro-5H-pyrazolo[1, 2-a][1, 2, 4]triazol-4-ium-6-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | BIAPENEM [MI] | Cgp 57148 | LJ C10, 627 | RPX2003

Specifications & Purity

Moligand™, 10mM in Water

Biochemical and Physiological Mechanisms

Highly broad spectrum antibiotic agent. Stable against dehydropeptidase I. Shows bactericidal effects against Gram-negative and Gram-positive aerobic and anaerobic bacteria, including β-lactamase producing species in vivo.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Names and Identifiers

• Canonical Smiles: CC1C2C(C(=O)N2C(=C1SC3CN4C=NC=[N+]4C3)C(=O)[O-])C(C)O
• IUPAC Name: (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-carboxylate
• InChIKey: MRMBZHPJVKCOMA-YJFSRANCSA-N
• 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
• Isomeric SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1SC3CN4C=NC=[N+]4C3)C(=O)[O-])[C@@H](C)O
• WGK Germany: 3
• Molecular Weight: 350.39
• Reaxy-Rn: 29458570
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=29458570&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Lactams
      • Subclass Beta lactams
        • Level5 Carbapenems
          • Level6 Thienamycins

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Lactams
• Subclass: Beta lactams
• Intermediate Tree Nodes: Carbapenems
• Direct Parent: Thienamycins
• Alternative Parents: Alpha amino acids and derivatives Pyrroline carboxylic acids Azepines Vinylogous thioesters Triazoles Tertiary carboxylic acid amides Heteroaromatic compounds Thioenol ethers Azetidines Carboxylic acid salts Secondary alcohols Monocarboxylic acids and derivatives Azacyclic compounds Carboxylic acids Sulfenyl compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Organic salts Organic zwitterions Organonitrogen compounds Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• 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
• Description: This compound 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.
• External Descriptors: organic sulfide - carbapenems - pyrazolotriazole

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

F2 Tclin Thrombin (11687 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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DPEP1 Tclin Renal dipeptidase (55 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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Homo sapiens (32628 Activities)

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Associated Targets(non-human)

blaZ Beta-lactamase (285 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Enterobacter cloacae (7976 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Proteus vulgaris (5823 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Klebsiella oxytoca (929 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Enterococcus faecalis (29875 Activities)

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Mus musculus (284745 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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blaVIM-2 Beta-lactamase VIM-2 (381 Activities)

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Plasma (328 Activities)

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pbpX Penicillin-binding protein 2x (156 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Moisture sensitive
• Molecular Weight: 350.400 g/mol
• XLogP3: 1.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 350.105 Da
• Monoisotopic Mass: 350.105 Da
• Topological Polar Surface Area: 128.000 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 609.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xuan Ma, Yue Wang, Wenting Wang, Jake Heinlein, Lisa D. Pfefferle, Xuemeng Tian.  (2023)  Strategic preparation of porous magnetic molecularly imprinted polymers via a simple and green method for high-performance adsorption and removal of meropenem.  TALANTA,      [PMID:36893497] [10.1016/j.talanta.2023.124419]