Ampicillin (CHEM016014)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:10:43 UTC
Update Date2016-11-09 01:15:19 UTC
Accession NumberCHEM016014
Identification
Common NameAmpicillin
ClassSmall Molecule
DescriptionAmpicillin is a semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass349.405 g/mol
Monoisotopic Mass349.110 g/mol
CAS Registry Number69-53-4
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
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 IdentifierInChI=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 penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentPenicillins
Alternative Parents
Substituents
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Azetidine
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Primary aliphatic amine
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Primary amine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-b00e3e20b6b67bd66c27Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2900000000-7b6c3a7162ec9326a246Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-f6004cc4fde6cc54c545Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-3446c37197fd7dc36a63Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2900000000-3160040d30aba5827731Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0901000000-9e9e3230339584136a97Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-b7dcea08c5f689065c5cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0901000000-c9400241d2ecd802485eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-6090000000-e84a46f7b56ca97f6265Spectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-07647be2cf284515b366Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052n-6924000000-83d903205df987b0b699Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-d97c7cfdd5c84d70b493Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0219000000-39936cb3e2a60642fccdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01x0-0914000000-4ad13ad2ef6dba0dd8f7Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00415
HMDB IDHMDB0014559
FooDB IDFDB020748
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDAIC
Wikipedia LinkAmpicillin
Chemspider ID6013
ChEBI ID28971
PubChem Compound ID6249
Kegg Compound IDC06574
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
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.
2. Rodevand E, Sletvold O, Kvande KT: [Side effects off allopurinol]. Tidsskr Nor Laegeforen. 2004 Oct 21;124(20):2618-9.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=10930630
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=12562703
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=12569987
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=12833570
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=14139119
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=14455820
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=15768449
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=16033609
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=18611716
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=19967069
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=2083978
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23568176
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23861268
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=24474427
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=24666465
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=25998949
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=28543395
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=6176550
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=8020088
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=9433938