Details of Metabolite

General Information of MET (ID: META00653)
Name Ampicillin
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2S,5R,6R)-6-[[(2R)-2-Amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylIC ACID; (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; (2S,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; (2S,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-(D(-)-alpha-Aminophenylacetamido)penicillanic acid; 6-(D-(2-Amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate; 6-(D-(2-Amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; 6-(a-Aminophenylacetamido)penicillanic acid; 6-D(-)-alpha-Aminophenylacetamido-penicillanic acid; 6-[(Aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 9ci; ABPC; AMP; AMPI; AP; AY 6108; Acillin; Adobacillin; Alpen; Amblosin; Amcill; Amfipen; Amfipen V; Aminobenzyl penicillin; Aminobenzylpenicillin; Amipenix S; Ampen; Ampi-bol; Ampi-co; Ampi-tab; Ampichel; Ampicil; Ampicilina; Ampicillin acid; Ampicillin anhydrate; Ampicillin anhydrous; Ampicillin base; Ampicillin sodium; Ampicillin trihydrate; Ampicillina; Ampicilline; Ampicillinum; Ampifarm; Ampikel; Ampimed; Ampipenin; Ampiscel; Ampisyn; Ampivax; Ampivet; Amplacilina; Amplin; Amplipenyl; Amplisom; Amplital; Anhydrous ampicillin; Antibiotic KS R1; Antibiotic KS-R1; Austrapen; BRL 1341; Bayer 5427; Binotal; Bonapicillin; Britacil; Campicillin; Cimex; Copharcilin; D-(-)-6-(a-Aminophenylacetamido)penicillanate; D-(-)-6-(a-Aminophenylacetamido)penicillanic acid; D-(-)-6-(alpha-Aminophenylacetamido)penicillanic acid; D-(-)-Ampicillin; D-(-)-alpha-Aminobenzylpenicillin; D-(-)-alpha-Aminopenicillin; D-Ampicillin; D-Cillin; D-a-Aminobenzylpenicillin; Delcillin; Deripen; Divercillin; Doktacillin; Duphacillin; Geocillin; Grampenil; Guicitrina; Guicitrine; KS-R1; KS-R1, Antibiotic; Lifeampil; Magnapen; Marcillin; Morepen; NSC 528986; Norobrittin; Novo-ampicillin; Nuvapen; Olin kid; Omnipen; Orbicilina; Pen a; Pen ampil; Penbristol; Penbritin; Penbrock; Penicillin, aminobenzyl; Penicline; Penimic; Pensyn; Pentrex; Pentrexl; Pentrexyl; Pentritin; Pfizerpen a; Polycillin; Ponecil; Princillin; Principen; Qidamp; Racenacillin; Ro-ampen; Rosampline; Roscillin; SK-Ampicillin; Semicillin; Servicillin; Sodium, ampicillin; Sumipanto; Supen; Synpenin; Texcillin; Tokiocillin; Tolomol; Totacillin; Totalciclina; Totapen; Trifacilina; Trihydrate, ampicillin; Ukapen; Ultrabion; Ultrabron; Vampen; Viccillin; Vidocillin; Vidopen; Wypicil; alpha-Aminobenzylpenicillin
Source Aromatic heteropolycyclic compounds
Structure Type   Ethers  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic oxygen compounds
Organooxygen compounds
Ethers
PubChem CID
6249
HMDB ID
HMDB0014559
Formula
C16H19N3O4S
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=6249"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C06574
DrugBank ID
DB00415
ChEBI ID
28971
FooDB ID
FDB020748
ChemSpider ID
6013
Physicochemical Properties Molecular Weight 349.4 Topological Polar Surface Area 138
XlogP -1.1 Complexity 562
Heavy Atom Count 24 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Function
Ampicillin is found in common pea. It is also a potential contaminant of cow's milk arising from its veterinary use. Ampicillin is a semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. It has been used extensively to treat bacterial infections since 1961. It is considered part of the aminopenicillin family and is roughly equivalent to amoxicillin in terms of spectrum and level of activity
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Leukotriene-C4 hydrolase (GGT1) 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 Knockdown (siRNA) of GGT1
                      Induced Change Ampicillin concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Renal cell carcinoma [ICD-11: 2C90]
                      Details It is reported that knockdown of GGT1 leads to the increase of ampicillin levels compared with control group.
      Nitrogen permease regulator (NPR)
            Natriuretic peptide receptor B (NPR2) 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 Deletion of NPR2
                      Induced Change Ampicillin concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that deletion of NPR2 leads to the decrease of ampicillin levels compared with control group.
      Transcription factor (TF)
            Myc proto-oncogene protein (MYC) 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 [3]
                      Introduced Variation Knockdown (siRNA) of MYC
                      Induced Change Ampicillin concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colorectal cancer [ICD-11: 2B91]
                      Details It is reported that knockdown of MYC leads to the decrease of ampicillin levels compared with control group.
      Transferases (EC 2)
            Pyridoxal kinase (PDXK) Click to Show/Hide the Full List of Regulating Pair(s):   2 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair (1) Experim Info click to show the details of experiment for validating this pair [4]
                      Introduced Variation Knockout (CRISPR/Cas9 sgRNA) of Pdxk
                      Induced Change Ampicillin concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Acute myeloid leukaemia [ICD-11: 2A60]
                      Details It is reported that knockout of Pdxk leads to the decrease of ampicillin levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [4]
                      Introduced Variation Knockout (CRISPR/Cas9 sgRNA) of PDXK
                      Induced Change Ampicillin concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Acute myeloid leukaemia [ICD-11: 2A60]
                      Details It is reported that knockout of PDXK leads to the decrease of ampicillin levels compared with control group.
            Transaldolase (TALDO1) 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 [5]
                      Introduced Variation Knockout of Taldo1
                      Induced Change Ampicillin concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Taldo1 leads to the decrease of ampicillin levels compared with control group.
References
1 Impairment of gamma-glutamyl transferase 1 activity in the metabolic pathogenesis of chromophobe renal cell carcinoma. Proc Natl Acad Sci U S A. 2018 Jul 3;115(27):E6274-E6282.
2 Npr2 inhibits TORC1 to prevent inappropriate utilization of glutamine for biosynthesis of nitrogen-containing metabolites. Sci Signal. 2014 Dec 16;7(356):ra120.
3 Global metabolic reprogramming of colorectal cancer occurs at adenoma stage and is induced by MYC. Proc Natl Acad Sci U S A. 2017 Sep 12;114(37):E7697-E7706.
4 Vitamin B6 Addiction in Acute Myeloid Leukemia. Cancer Cell. 2020 Jan 13;37(1):71-84.e7.
5 Two isoforms of TALDO1 generated by alternative translational initiation show differential nucleocytoplasmic distribution to regulate the global metabolic network. Sci Rep. 2016 Oct 5;6:34648.

If you find any error in data or bug in web service, please kindly report it to Dr. Zhang and Dr. Mou.