Details of Metabolite

General Information of MET (ID: META00660)
Name Penicillin G
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-(2-Phenylacetamido)penicillanate; 6-(2-Phenylacetamido)penicillanic acid; Antibioticos brand OF penicillin g sodium; Bencilpenicilina; Benpen; Bensylpenicillin; Benzyl benicillin; Benzylpenicillin; Benzylpenicillin potassium; Benzylpenicillinate; Benzylpenicilline; Benzylpenicillinic acid; Benzylpenicillinum; Bioniche brand OF penicillin g sodium; Britannia brand OF penicillin g sodium; CSL Brand OF penicillin g sodium; Clonmel brand OF penicillin g sodium; Coliriocilina; Crystapen; Ern brand OF penicillin g sodium; Free penicillin II; Jenapharm brand OF penicillin g sodium; Lakeside brand OF penicillin g sodium; Llorente brand OF penicillin g sodium; Medical brand OF penicillin g potassium; Medical brand OF penicillin g sodium; Or-pen; Ortega brand OF penicillin g potassium; PCG; PG; Parcillin; Parmed brand OF penicillin g potassium; Pekamin; Pengesod; Penibiot; Penicilina g llorente; Penicillin g; Penicillin g jenapharm; Penicillin g potassium; Penicillin g sodium; Penilevel; Peniroger; Pfizer brand OF penicillin g potassium; Pfizerpen; Sodiopen; Sodipen; Sodium benzylpenicillin; Sodium penicillin; UCB brand OF penicillin g sodium; Unicilina; Ursopen; Van-pen-g; Vangard brand OF penicillin g potassium
Source Aromatic heteropolycyclic compounds
Structure Type   Amino acids, peptides, and analogues  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Carboxylic acids and derivatives
Amino acids, peptides, and analogues
PubChem CID
5904
HMDB ID
HMDB0015186
Formula
C16H18N2O4S
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C05551
DrugBank ID
DB01053
ChEBI ID
18208
ChemSpider ID
5693
Physicochemical Properties Molecular Weight 334.4 Topological Polar Surface Area 112
XlogP 1.8 Complexity 530
Heavy Atom Count 23 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Function
Penicillin G is narrow spectrum antibiotic used to treat infections caused by susceptible bacteria. It is a natural penicillin antibiotic that is administered intravenously or intramuscularly due to poor oral absorption. Penicillin G may also be used in some cases as prophylaxis against susceptible organisms. Natural penicillins are considered the drugs of choice for several infections caused by susceptible gram positive aerobic organisms, such as <i>Streptococcus pneumoniae</i>, groups A, B, C and G streptococci, nonenterococcal group D streptococci, viridans group streptococci, and non-penicillinase producing staphylococcus. Aminoglycosides may be added for synergy against group B streptococcus (<i>S. agalactiae</i>), <i>S. viridans</i>, and <i>Enterococcus faecalis</i>. The natural penicillins may also be used as first or second line agents against susceptible gram positive aerobic bacilli such as <i>Bacillus anthracis</i>, <i>Corynebacterium diphtheriae</i>, and <i>Erysipelothrix rhusiopathiae</i>. Natural penicillins have limited activity against gram negative organisms; however, they may be used in some cases to treat infections caused by <i>Neisseria meningitidis</i> and <i>Pasteurella</i>. They are not generally used to treat anaerobic infections. Resistance patterns, susceptibility and treatment guidelines vary across regions.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Organo anion transporter (OAT)
            Organic anion transporter D (SLCO3A1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Overexpression of SLCO3A1
                      Induced Change Penicillin G concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLCO3A1 leads to the increase of penicillin G levels compared with control group.
            Organic anion transporter E (SLCO4A1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Overexpression of SLCO4A1
                      Induced Change Penicillin G concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLCO4A1 leads to the increase of penicillin G levels compared with control group.
            Solute carrier SLCO1B1 (OATP-C) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Overexpression of SLCO1B1
                      Induced Change Penicillin G concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLCO1B1 leads to the increase of penicillin G levels compared with control group.
            Solute carrier SLCO2B1 (OATPB) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Overexpression of SLCO2B1
                      Induced Change Penicillin G concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLCO2B1 leads to the increase of penicillin G levels compared with control group.
      Transferases (EC 2)
            Arylamine N-acetyltransferase 1 (NAT1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockout of NAT1
                      Induced Change Penicillin G concentration: increase (FC = 18.2)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Breast cancer [ICD-11: 2C60]
                      Details It is reported that knockout of NAT1 leads to the increase of penicillin G levels compared with control group.
References
1 Molecular identification and characterization of novel members of the human organic anion transporter (OATP) family. Biochem Biophys Res Commun. 2000 Jun 24;273(1):251-60.
2 CRISPR/Cas9 knockout of human arylamine N-acetyltransferase 1 in MDA-MB-231 breast cancer cells suggests a role in cellular metabolism. Sci Rep. 2020 Jun 17;10(1):9804.

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