Detailed information for compound 169308

Basic information

Technical information
  • TDR Targets ID: 169308
  • Name: sodium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-ph enylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]h eptane-2-carboxylate
  • MW: 356.372 | Formula: C16H17N2NaO4S
  • H donors: 1 H acceptors: 4 LogP: 1.95 Rotable bonds: 5
    Rule of 5 violations (Lipinski): 1
  • SMILES: O=C(Cc1ccccc1)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C.[Na+]
  • InChi: 1S/C16H18N2O4S.Na/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);/q;+1/p-1/t11-,12+,14-;/m1./s1
  • InChiKey: FCPVYOBCFFNJFS-LQDWTQKMSA-M  


Substructure search Similarity search

Network

Hover on a compound node to display the structore

Synonyms

  • sodium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(1-oxo-2-phenylethyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  • sodium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylethanoylamino)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  • sodium (2S,5R,6R)-7-keto-3,3-dimethyl-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  • Penicillin G
  • 8049-60-3
  • 69-57-8
  • 1406-09-3
  • PENNA_SIGMA
  • CAS-69-57-8
  • NCGC00017015-01
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenylacetyl)amino)-, (2S-(2alpha,5alpha,6beta))-, monosodium salt
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-, monosodium salt
  • American penicillin
  • BENZYLPENICILLIN SODIUM SALT
  • Benzylpenicillin sodium
  • Benzylpenicillinic acid sodium salt
  • Crystapen
  • EINECS 200-710-2
  • Kesso-Pen
  • Monosodium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate
  • Monosodium benzylpenicillin
  • Mycofarm
  • NSC 402815
  • Novocillin
  • OK 431
  • Pen-A-Brasive
  • Pencillin G sodium
  • Penicillin G Sodium [USAN]
  • Penicillin G Sodium, Crystalline
  • Penicillin G, sodium
  • Penicillin-G, monosodium salt
  • Penilaryn
  • Sodium (2S-(2alpha,5alpha,6beta))-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate
  • Sodium 6-(phenylacetamido)penicillanate
  • Sodium benzylpenicillin
  • Sodium benzylpenicillin G
  • Sodium benzylpenicillinate
  • Sodium benzylpenicyllinate
  • Sodium penicillin
  • Sodium penicillin G
  • Sodium penicillin II
  • Sugracillin sodium salt
  • Veticillin
  • Penicillin G sodium salt
  • D05408
  • Penicillin G sodium (TN)
  • Penicillin G sodium (USP)
  • P3032_SIGMA

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Mycobacterium leprae Probable cysteine:1D-myo-inosityl 2-amino-2-deoxy--D-glucopyranoside ligase MshC Curated by TDR Targets References
Mycobacterium tuberculosis Cysteine:1D-myo-inosityl 2-amino-2-deoxy--D-glucopyranoside ligase MshC Curated by TDR Targets References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Mycobacterium tuberculosis Cysteine:1D-myo-inosityl 2-amino-2-deoxy--D-glucopyranoside ligase MshC Get druggable targets OG5_237682 All targets in OG5_237682
Mycobacterium leprae Probable cysteine:1D-myo-inosityl 2-amino-2-deoxy--D-glucopyranoside ligase MshC Get druggable targets OG5_237682 All targets in OG5_237682
Mycobacterium ulcerans cysteinyl-tRNA synthetase Get druggable targets OG5_237682 All targets in OG5_237682
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Wolbachia endosymbiont of Brugia malayi cysteinyl-tRNA synthetase Probable cysteine:1D-myo-inosityl 2-amino-2-deoxy--D-glucopyranoside ligase MshC 412 aa 353 aa 32.3 %
Wolbachia endosymbiont of Brugia malayi cysteinyl-tRNA synthetase Cysteine:1D-myo-inosityl 2-amino-2-deoxy--D-glucopyranoside ligase MshC 414 aa 378 aa 31.5 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Echinococcus multilocularis cysteinyl tRNA synthetase 0.0048 0.0095 0.0377
Leishmania major mitochondrial DNA polymerase beta 0.0323 0.0933 1
Loa Loa (eye worm) MH2 domain-containing protein 0.0246 0.0699 0.8321
Trypanosoma cruzi DNA polymerase beta thumb, putative 0.0045 0.0087 0.0835
Trypanosoma brucei mitochondrial DNA polymerase beta 0.0323 0.0933 1
Giardia lamblia Cysteinyl-tRNA synthetase 0.0048 0.0095 1
Trichomonas vaginalis glutaminase, putative 0.0292 0.084 1
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0045 0.0085 0.0337
Schistosoma mansoni hypothetical protein 0.0166 0.0455 0.5414
Loa Loa (eye worm) glutaminase 0.0292 0.084 1
Echinococcus granulosus cysteinyl tRNA synthetase 0.0048 0.0095 0.21
Brugia malayi exodeoxyribonuclease III family protein 0.002 0.001 0.0121
Echinococcus multilocularis geminin 0.0166 0.0455 0.1795
Wolbachia endosymbiont of Brugia malayi cysteinyl-tRNA synthetase 0.0048 0.0095 1
Onchocerca volvulus 0.0048 0.0095 0.5
Mycobacterium ulcerans cysteinyl-tRNA synthetase 0.0048 0.0095 0.0085
Toxoplasma gondii cysteine-tRNA synthetase (CysRS) 0.0048 0.0095 0.8751
Brugia malayi MH2 domain containing protein 0.0246 0.0699 0.8321
Echinococcus granulosus DNA apurinic or apyrimidinic site lyase 0.002 0.001 0.0224
Trypanosoma cruzi cysteinyl-tRNA synthetase, putative 0.0048 0.0095 0.0924
Trypanosoma brucei DNA polymerase beta thumb, putative 0.0045 0.0087 0.0835
Trypanosoma cruzi mitochondrial DNA polymerase beta-PAK, putative 0.0153 0.0415 0.4383
Echinococcus multilocularis atpase aaa+ type core atpase aaa type core 0.0847 0.2532 1
Schistosoma mansoni ap endonuclease 0.002 0.001 0.0121
Trypanosoma cruzi mitochondrial DNA polymerase beta, putative 0.0323 0.0933 1
Loa Loa (eye worm) glutaminase 2 0.0292 0.084 1
Plasmodium falciparum cysteine--tRNA ligase 0.0048 0.0095 1
Loa Loa (eye worm) hypothetical protein 0.0048 0.0095 0.1137
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0045 0.0085 0.1017
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0045 0.0085 0.0337
Schistosoma mansoni ap endonuclease 0.002 0.001 0.0121
Mycobacterium tuberculosis Cysteine:1D-myo-inosityl 2-amino-2-deoxy--D-glucopyranoside ligase MshC 0.3296 1 1
Echinococcus multilocularis DNA (apurinic or apyrimidinic site) lyase 0.002 0.001 0.004
Brugia malayi GTP-binding regulatory protein Gs alpha-S chain, putative 0.0045 0.0085 0.1017
Mycobacterium tuberculosis Conserved hypothetical protein 0.017 0.0467 0.0458
Chlamydia trachomatis cysteine--tRNA ligase 0.0048 0.0095 0.5
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0045 0.0085 0.1879
Trypanosoma cruzi mitochondrial DNA polymerase beta-PAK, putative 0.0055 0.0118 0.1163
Mycobacterium ulcerans hypothetical protein 0.017 0.0467 0.0458
Schistosoma mansoni cysteinyl-tRNA synthetase 0.0048 0.0095 0.1137
Entamoeba histolytica cysteinyl-tRNA synthetase, putative 0.0048 0.0095 1
Leishmania major mitochondrial DNA polymerase beta-PAK, putative 0.0153 0.0415 0.4383
Toxoplasma gondii hypothetical protein 0.0052 0.0108 1
Treponema pallidum cysteinyl-tRNA synthetase 0.0048 0.0095 1
Trypanosoma cruzi mitochondrial DNA polymerase beta-PAK, putative 0.0045 0.0087 0.0835
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0045 0.0085 0.1017
Schistosoma mansoni cysteinyl-tRNA synthetase 0.0048 0.0095 0.1137
Plasmodium vivax cysteine--tRNA ligase, putative 0.0048 0.0095 1
Echinococcus granulosus geminin 0.0166 0.0455 1
Trichomonas vaginalis cysteinyl-tRNA synthetase, putative 0.0048 0.0095 0.1028
Mycobacterium ulcerans cysteinyl-tRNA synthetase 0.3296 1 1
Loa Loa (eye worm) exodeoxyribonuclease III family protein 0.002 0.001 0.0121
Trypanosoma brucei cysteinyl-tRNA synthetase, putative 0.0048 0.0095 0.0924
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0045 0.0085 0.1017
Loa Loa (eye worm) transcription factor SMAD2 0.0246 0.0699 0.8321
Loa Loa (eye worm) cysteinyl tRNA synthetase 1 0.0048 0.0095 0.1137
Trypanosoma cruzi cysteinyl-tRNA synthetase, putative 0.0048 0.0095 0.0924
Trypanosoma cruzi mitochondrial DNA polymerase beta, putative 0.0323 0.0933 1
Brugia malayi cysteinyl tRNA synthetase protein 1 0.0048 0.0095 0.1137
Mycobacterium ulcerans glutaminase 0.0292 0.084 0.083
Echinococcus granulosus leucyl tRNA synthetase 0.0048 0.0095 0.21
Leishmania major cysteinyl-tRNA synthetase, putative 0.0048 0.0095 0.0924
Loa Loa (eye worm) GTP-binding regulatory protein Gs alpha-S chain 0.0045 0.0085 0.1017
Schistosoma mansoni hypothetical protein 0.0166 0.0455 0.5414
Plasmodium falciparum cysteine--tRNA ligase 0.0048 0.0095 1
Brugia malayi glutaminase DH11.1 0.0292 0.084 1
Trypanosoma cruzi DNA polymerase beta thumb, putative 0.0045 0.0087 0.0835
Schistosoma mansoni glutaminase 0.0292 0.084 1
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0045 0.0085 0.1879
Trypanosoma brucei mitochondrial DNA polymerase beta-PAK 0.0153 0.0415 0.4383

Activities

Activity type Activity value Assay description Source Reference
AC50 (functional) PUBCHEM_BIOASSAY: Cytochrome panel assay with activity outcomes. (Class of assay: other) Panel member name: p450-cyp2d6 Compounds with AC50 equal or less than 10 uM are considered active ChEMBL. No reference
AC50 (functional) PUBCHEM_BIOASSAY: Cytochrome panel assay with activity outcomes. (Class of assay: other) Panel member name: p450-cyp3a4 Compounds with AC50 equal or less than 10 uM are considered active ChEMBL. No reference
AC50 (functional) PUBCHEM_BIOASSAY: Cytochrome panel assay with activity outcomes. (Class of assay: other) Panel member name: p450-cyp2c19 Compounds with AC50 equal or less than 10 uM are considered active ChEMBL. No reference
AC50 (functional) PUBCHEM_BIOASSAY: Cytochrome panel assay with activity outcomes. (Class of assay: other) Panel member name: p450-cyp1a2 Compounds with AC50 equal or less than 10 uM are considered active ChEMBL. No reference
AC50 (functional) PUBCHEM_BIOASSAY: Cytochrome panel assay with activity outcomes. (Class of assay: other) Panel member name: p450-cyp2c9 Compounds with AC50 equal or less than 10 uM are considered active ChEMBL. No reference
Antibiotic resistance (functional) Compound was tested for photoinhibition of E. coli (CIP 548T); No data ChEMBL. 9873665
Antibiotic resistance (functional) 0 Compound was tested for photoinhibition of E. coli (CIP 548T); No data ChEMBL. 9873665
Antibiotic resistance (functional) 0 Compound was tested for photoinhibition of Staphylococcus aureus(CIP 53156); Sensitive ChEMBL. 9873665
Ki (binding) = 3.34 Inhibition of mouse Oat6-mediated [3H]ES uptake in Xenopus oocytes after 1 hr ChEMBL. 17553798
Ki (binding) = 3.48 Inhibition of mouse Oat1-mediated [3H]PAH uptake in Xenopus oocytes after 1 hr ChEMBL. 17553798
Ki (binding) = 328 uM Inhibition of mouse Oat1-mediated [3H]PAH uptake in Xenopus oocytes after 1 hr ChEMBL. 17553798
Ki (binding) = 452 uM Inhibition of mouse Oat6-mediated [3H]ES uptake in Xenopus oocytes after 1 hr ChEMBL. 17553798
MIC (functional) Antifungal activity against Candida albicans ATCC 10231 after 24 hrs by NCCLS M38-P broth dilution method ChEMBL. 21641699
MIC (functional) = 0.78 ug ml-1 Antibacterial activity against Escherichia coli ATCC 11303 after 24 hrs by NCCLS M7-A6 broth dilution method ChEMBL. 21641699
MIC50 (functional) Antimicrobial activity against Escherichia coli ATCC 8739 by MTT assay ChEMBL. 26404408
MIC80 (functional) = 0.78 ug ml-1 Antibacterial activity against 1 x 10'4 cfu/mL Escherichia coli ATCC 11303 after 24 hrs by NCCLS M7-A6 microtiter broth dilution method ChEMBL. 21570749
MIC80 (functional) = 0.78 ug ml-1 Antibacterial activity against Escherichia coli ATCC 11303 after 24 hrs by microtiter broth dilution method ChEMBL. 22673144
MIC90 (functional) 0 ug ml-1 Minimum inhibitory concentration required for primary screening against in-house strain of Haemophilus influenzae tested in vitro; ND- Not determined ChEMBL. 14684298
MIC90 (functional) 0 ug ml-1 Minimum inhibitory concentration required for primary screening against in-house strain of Moraxella catarrhalis tested in vitro; ND- Not determined ChEMBL. 14684298
MIC90 (functional) = 1 ug ml-1 Minimum inhibitory concentration required for primary screening against in-house strain of Streptococcus pneumoniae tested in vitro; Range-0.008-2 ChEMBL. 14684298

Phenotypes

Whole-cell/tissue/organism interactions

We have no records of whole-cell/tissue assays done with this compound What does this mean?

Many chemical entities in TDR Targets come from high-throughput screenings with whole cells or tissue samples, and not all assayed compounds have been tested against a single a single target protein, probably because they get ruled out during screening process. Even if these compounds may have not been of interest in the original screening, they may come as interesting leads for other screening assays. Furthermore, we may be able to propose drug-target associations using chemical similarities and network patterns.

Annotated phenotypes:

Affected Entity Phenotypic quality Occurs in Occurs at Evidence Observed in Targets
response to drug (GO:0042493) increased sensitivity toward (PATO:0001549) inferred from loss-of-function mutant phenotype (ECO:0000016) Mycobacterium tuberculosis 257260  
Annotator: crowther@u.washington.edu Comment: 2007-12-26 References: 12384335
response to drug (GO:0042493) increased sensitivity toward (PATO:0001549) inferred from loss-of-function mutant phenotype (ECO:0000016) Mycobacterium tuberculosis 6539  
Annotator: crowther@u.washington.edu Comment: 2007-12-26 References: 12384335

In TDR Targets, information about phenotypes that are caused by drugs, or by genetic manipulation of cells (e.g. gene knockouts or knockdowns) is manually curated from the literature. These descriptions help to describe the potential of the target for drug development. If no information is available for this gene or if the information is incomplete, this may mean that i) the papers containing this information either appeared after the curation effort for this organism was carried out or they were inadvertently missed by curators; or that ii) the curation effort for this organism has not yet started.
 
In any case, if you have information about papers containing relevant validation data for this target, please log in using your TDR Targets username and password and send them to us using the corresponding form in this page (only visible to registered users) or contact us.

External resources for this compound

Bibliographic References

43 literature references were collected for this gene.

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