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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:53 UTC
HMDB IDHMDB0014559
Secondary Accession Numbers
  • HMDB0030484
  • HMDB14559
  • HMDB30484
Metabolite Identification
Common NameAmpicillin
DescriptionAmpicillin, also known as AMP or acillin, belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Ampicillin interferes with an autolysin inhibitor. Ampicillin is a drug which is used for treatment of infection (respiratory, gi, uti and meningitis) due to e. coli, p. mirabilis, enterococci, shigella, s. typhosa and other salmonella, nonpenicillinase-producing n. gononhoeae, h. influenzae, staphylococci, streptococci including streptoc. Ampicillin is a very strong basic compound (based on its pKa). The bactericidal activity of Ampicillin results from the inhibition of cell wall synthesis and is mediated through Ampicillin binding to penicillin binding proteins (PBPs). The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Ampicillin inhibits the third and last stage of bacterial cell wall synthesis. Ampicillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. Ampicillin is a semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. Ampicillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases. Ampicillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria.
Structure
Data?1582753193
Synonyms
ValueSource
(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 acidChEBI
(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 ACIDChEBI
(2S,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
6-(D-(2-Amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acidChEBI
ABPCChEBI
AminobenzylpenicillinChEBI
AMPChEBI
AmpicilinaChEBI
Ampicillin acidChEBI
Ampicillin anhydrousChEBI
AmpicillineChEBI
AmpicillinumChEBI
Anhydrous ampicillinChEBI
APChEBI
D-(-)-6-(alpha-Aminophenylacetamido)penicillanic acidChEBI
D-(-)-AmpicillinChEBI
OmnipenKegg
(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
(2S,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
6-(D-(2-Amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylateGenerator
D-(-)-6-(a-Aminophenylacetamido)penicillanateGenerator
D-(-)-6-(a-Aminophenylacetamido)penicillanic acidGenerator
D-(-)-6-(alpha-Aminophenylacetamido)penicillanateGenerator
D-(-)-6-(Α-aminophenylacetamido)penicillanateGenerator
D-(-)-6-(Α-aminophenylacetamido)penicillanic acidGenerator
(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 acidHMDB
6-(a-Aminophenylacetamido)penicillanic acidHMDB
6-(D(-)-alpha-Aminophenylacetamido)penicillanic acidHMDB
6-D(-)-alpha-Aminophenylacetamido-penicillanic acidHMDB
6-[(Aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 9ciHMDB
AcillinHMDB
AdobacillinHMDB
AlpenHMDB
alpha-AminobenzylpenicillinHMDB
AmblosinHMDB
AmcillHMDB
AmfipenHMDB
Amfipen VHMDB
Amipenix SHMDB
AmpenHMDB
AMPIHMDB
Ampi-bolHMDB
Ampi-coHMDB
Ampi-tabHMDB
AmpichelHMDB
AmpicilHMDB
Ampicillin anhydrateHMDB
Ampicillin baseHMDB
Ampicillin sodiumHMDB
Ampicillin trihydrateHMDB
AmpicillinaHMDB
AmpifarmHMDB
AmpikelHMDB
AmpimedHMDB
AmpipeninHMDB
AmpiscelHMDB
AmpisynHMDB
AmpivaxHMDB
AmpivetHMDB
AmplacilinaHMDB
AmplinHMDB
AmplipenylHMDB
AmplisomHMDB
AmplitalHMDB
AustrapenHMDB
AY 6108HMDB
Bayer 5427HMDB
BinotalHMDB
BonapicillinHMDB
BritacilHMDB
BRL 1341HMDB
CampicillinHMDB
CimexHMDB
CopharcilinHMDB
D-(-)-alpha-AminobenzylpenicillinHMDB
D-(-)-alpha-AminopenicillinHMDB
D-a-AminobenzylpenicillinHMDB
D-AmpicillinHMDB
D-CillinHMDB
DelcillinHMDB
DeripenHMDB
DivercillinHMDB
DoktacillinHMDB
DuphacillinHMDB
GeocillinHMDB
GrampenilHMDB
GuicitrinaHMDB
GuicitrineHMDB
KS-R1HMDB
LifeampilHMDB
MagnapenHMDB
MarcillinHMDB
MorepenHMDB
NorobrittinHMDB
Novo-ampicillinHMDB
NSC 528986HMDB
NuvapenHMDB
Olin kidHMDB
OrbicilinaHMDB
Pen aHMDB
Pen ampilHMDB
PenbristolHMDB
PenbritinHMDB
PenbrockHMDB
PeniclineHMDB
PenimicHMDB
PensynHMDB
PentrexHMDB
PentrexlHMDB
PentrexylHMDB
PentritinHMDB
Pfizerpen aHMDB
PolycillinHMDB
PonecilHMDB
PrincillinHMDB
PrincipenHMDB
QidampHMDB
RacenacillinHMDB
Ro-ampenHMDB
RosamplineHMDB
RoscillinHMDB
SemicillinHMDB
ServicillinHMDB
SK-AmpicillinHMDB
SumipantoHMDB
SupenHMDB
SynpeninHMDB
TexcillinHMDB
TokiocillinHMDB
TolomolHMDB
TotacillinHMDB
TotalciclinaHMDB
TotapenHMDB
TrifacilinaHMDB
UkapenHMDB
UltrabionHMDB
UltrabronHMDB
VampenHMDB
ViccillinHMDB
VidocillinHMDB
VidopenHMDB
WypicilHMDB
Aminobenzyl penicillinHMDB
Antibiotic KS R1HMDB
KS-R1, AntibioticHMDB
Sodium, ampicillinHMDB
Antibiotic KS-R1HMDB
Penicillin, aminobenzylHMDB
Trihydrate, ampicillinHMDB
Chemical FormulaC16H19N3O4S
Average Molecular Weight349.405
Monoisotopic Molecular Weight349.109626801
IUPAC Name(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Nameampicillin
CAS Registry Number69-53-4
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
InChI KeyAVKUERGKIZMTKX-NJBDSQKTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentDiarylethers
Alternative Parents
Substituents
  • Diaryl ether
  • Tetrahydroisoquinoline
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Benzenoid
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic zwitterion
  • Organic salt
  • Organic iodide salt
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point208 °CPhysProp
Boiling PointNot AvailableNot Available
Water Solubility10100 mg/L (at 21 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP1.35SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.6 g/LALOGPS
logP0.88ALOGPS
logP-2ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.73 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity87.52 m³·mol⁻¹ChemAxon
Polarizability34.54 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1900000000-328e5756b2a2047f3401Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-1900000000-49339d5b1f688b0249b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-1349000000-51be76a1d965184221c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9810000000-75530784e97a116633e5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9600000000-0f235a2c675944bd7f8aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-006x-9300000000-766d3a6fea596a3f18a8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9100000000-147bdc3aaa0be3d0b419Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bt9-1912000000-75f97354ed9ba956615bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-2910000000-96d30028da61376db9b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-7900000000-eff889c1fe387a213319Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0291000000-98a4e819f450d352aea4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1591000000-eaed25e7ad3d86ca1564Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05di-9520000000-3b6aedcd44ff9d287dc0Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00415 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00415 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00415
Phenol Explorer Compound IDNot Available
FooDB IDFDB020748
KNApSAcK IDNot Available
Chemspider ID6013
KEGG Compound IDC06574
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmpicillin
METLIN IDNot Available
PubChem Compound6249
PDB IDAIC
ChEBI ID28971
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mo BH: [Clinical analysis of 410 cases of drug eruption]. Di Yi Jun Yi Da Xue Xue Bao. 2003 Feb;23(2):183, 186. [PubMed:12581979 ]
  2. Rodevand E, Sletvold O, Kvande KT: [Side effects off allopurinol]. Tidsskr Nor Laegeforen. 2004 Oct 21;124(20):2618-9. [PubMed:15534635 ]
  3. Kadurugamuwa JL, Hengstler B, Zak O: Cerebrospinal fluid protein profile in experimental pneumococcal meningitis and its alteration by ampicillin and anti-inflammatory agents. J Infect Dis. 1989 Jan;159(1):26-34. [PubMed:2462602 ]
  4. Crivaro V, Bagattini M, Salza MF, Raimondi F, Rossano F, Triassi M, Zarrilli R: Risk factors for extended-spectrum beta-lactamase-producing Serratia marcescens and Klebsiella pneumoniae acquisition in a neonatal intensive care unit. J Hosp Infect. 2007 Oct;67(2):135-41. Epub 2007 Sep 19. [PubMed:17884248 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular weight:
62751.1
References
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865 ]
General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular weight:
78805.3
References
  1. Covitz KM, Amidon GL, Sadee W: Human dipeptide transporter, hPEPT1, stably transfected into Chinese hamster ovary cells. Pharm Res. 1996 Nov;13(11):1631-4. [PubMed:8956326 ]
  2. Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ: Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther. 1999 Apr;289(1):448-54. [PubMed:10087037 ]
  3. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]
  4. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]
General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular weight:
81782.8
References
  1. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]
  2. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]