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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:01 UTC
HMDB IDHMDB0015540
Secondary Accession Numbers
  • HMDB15540
Metabolite Identification
Common NameBacampicillin
DescriptionBacampicillin is a prodrug of ampicillin and is microbiologically inactive. It is absorbed following oral administration. During absorption from the gastrointestinal tract, bacampicillin is hydrolyzed by esterases present in the intestinal wall. It is microbiologically active as ampicillin, and exerts a bactericidal action through the inhibition of the biosynthesis of cell wall mucopeptides. It is used to cure infection of upper and lower respiratory tract; skin and soft tissue; urinary tract and acute uncomplicated gonococcal urethritis etc.
Structure
Data?1582753308
Synonyms
ValueSource
1'-Ethoxycarbonyloxyethyl-(6-D-alpha-aminophenylacetamido)penicillanateChEBI
1-[(Ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateChEBI
BacampicilinaChEBI
BacampicillineChEBI
BacampicillinumChEBI
PenglobeKegg
1'-Ethoxycarbonyloxyethyl-(6-D-a-aminophenylacetamido)penicillanateGenerator
1'-Ethoxycarbonyloxyethyl-(6-D-a-aminophenylacetamido)penicillanic acidGenerator
1'-Ethoxycarbonyloxyethyl-(6-D-alpha-aminophenylacetamido)penicillanic acidGenerator
1'-Ethoxycarbonyloxyethyl-(6-D-α-aminophenylacetamido)penicillanateGenerator
1'-Ethoxycarbonyloxyethyl-(6-D-α-aminophenylacetamido)penicillanic acidGenerator
1-[(Ethoxycarbonyl)oxy]ethyl (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 acidGenerator
BAPCHMDB
Bacampicillin hydrochlorideHMDB
Bacampicillin monohydrochlorideHMDB
Ethoxycarbonyloxyethyl ester OF ampicillinHMDB
BacampicineHMDB
CarampicillinHMDB
Chemical FormulaC21H27N3O7S
Average Molecular Weight465.52
Monoisotopic Molecular Weight465.156970923
IUPAC Name1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Traditional Namebacampicillin
CAS Registry Number50972-17-3
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OC(C)OC(=O)OCC
InChI Identifier
InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1
InChI KeyPFOLLRNADZZWEX-FFGRCDKISA-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
  • Alpha-amino acid ester
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Aralkylamine
  • Monocyclic benzene moiety
  • Carbonic acid diester
  • Benzenoid
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Azetidine
  • Carbonic acid derivative
  • Carboxamide group
  • Carboxylic acid ester
  • Hemithioaminal
  • Thioether
  • Dialkylthioether
  • Azacycle
  • Acetal
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Primary amine
  • Primary aliphatic amine
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.12 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP1.17ALOGPS
logP1.47ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)11.72ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area137.26 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity113.76 m³·mol⁻¹ChemAxon
Polarizability46.8 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+205.51331661259
DarkChem[M-H]-200.41931661259
DeepCCS[M-2H]-243.13530932474
DeepCCS[M+Na]+217.81530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Bacampicillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OC(C)OC(=O)OCC4127.8Standard polar33892256
Bacampicillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OC(C)OC(=O)OCC2878.2Standard non polar33892256
Bacampicillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OC(C)OC(=O)OCC3252.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bacampicillin,1TMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C3210.3Semi standard non polar33892256
Bacampicillin,1TMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C2989.6Standard non polar33892256
Bacampicillin,1TMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C4666.6Standard polar33892256
Bacampicillin,1TMS,isomer #2CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C3118.8Semi standard non polar33892256
Bacampicillin,1TMS,isomer #2CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C2952.5Standard non polar33892256
Bacampicillin,1TMS,isomer #2CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C4893.0Standard polar33892256
Bacampicillin,2TMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C3177.6Semi standard non polar33892256
Bacampicillin,2TMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C3035.1Standard non polar33892256
Bacampicillin,2TMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C4185.4Standard polar33892256
Bacampicillin,2TMS,isomer #2CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C3243.9Semi standard non polar33892256
Bacampicillin,2TMS,isomer #2CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C3103.5Standard non polar33892256
Bacampicillin,2TMS,isomer #2CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C4396.4Standard polar33892256
Bacampicillin,3TMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C3266.0Semi standard non polar33892256
Bacampicillin,3TMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C3150.9Standard non polar33892256
Bacampicillin,3TMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C3963.8Standard polar33892256
Bacampicillin,1TBDMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C3385.4Semi standard non polar33892256
Bacampicillin,1TBDMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C3187.7Standard non polar33892256
Bacampicillin,1TBDMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C4675.3Standard polar33892256
Bacampicillin,1TBDMS,isomer #2CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C3321.8Semi standard non polar33892256
Bacampicillin,1TBDMS,isomer #2CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C3145.6Standard non polar33892256
Bacampicillin,1TBDMS,isomer #2CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C4884.4Standard polar33892256
Bacampicillin,2TBDMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C3510.8Semi standard non polar33892256
Bacampicillin,2TBDMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C3424.6Standard non polar33892256
Bacampicillin,2TBDMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C4323.9Standard polar33892256
Bacampicillin,2TBDMS,isomer #2CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C3640.3Semi standard non polar33892256
Bacampicillin,2TBDMS,isomer #2CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C3455.9Standard non polar33892256
Bacampicillin,2TBDMS,isomer #2CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C4460.3Standard polar33892256
Bacampicillin,3TBDMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C3792.2Semi standard non polar33892256
Bacampicillin,3TBDMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C3692.5Standard non polar33892256
Bacampicillin,3TBDMS,isomer #1CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C4159.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bacampicillin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1900000000-210a80ea99d7d8b19c7c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bacampicillin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bacampicillin 10V, Positive-QTOFsplash10-052f-5914100000-b2bb79f625d3a39bd0722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bacampicillin 20V, Positive-QTOFsplash10-0a4l-7911000000-c5d3cfc8023d3a8d1c162016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bacampicillin 40V, Positive-QTOFsplash10-0a4i-6910000000-bb9f92cfef936fcb5cab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bacampicillin 10V, Negative-QTOFsplash10-0a4i-0391100000-56ef32146ff2caf816af2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bacampicillin 20V, Negative-QTOFsplash10-0a4i-8593000000-92004702bfb034e6fad92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bacampicillin 40V, Negative-QTOFsplash10-056r-9510000000-079171b8e9ca83a521cb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bacampicillin 10V, Positive-QTOFsplash10-0aos-0417900000-e6199826945c6f15ce9f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bacampicillin 20V, Positive-QTOFsplash10-0adi-2639600000-ef04d08a127b82678b0b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bacampicillin 40V, Positive-QTOFsplash10-0a4i-4910000000-ff0f3c2bb5b4f7c583502021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bacampicillin 10V, Negative-QTOFsplash10-0079-9015000000-d06a5bb09c37d08d5b912021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bacampicillin 20V, Negative-QTOFsplash10-03dj-9310000000-e4b469c81aee8f9b372c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bacampicillin 40V, Negative-QTOFsplash10-0006-9120000000-b9b13300295f6383c3782021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01602 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01602 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01602
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID390135
KEGG Compound IDC08122
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBacampicillin
METLIN IDNot Available
PubChem Compound441397
PDB IDNot Available
ChEBI ID2968
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available