Ampicillin
Athanor · official
C16H19N3O4S · 349.4 g/mol
IUPAC name: 6-[(2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Also called Principen, aminopenicillin, beta-lactam
Names and identifiers
- IUPAC name
- 6-[(2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- Synonyms
- Principen, aminopenicillin, beta-lactam
+ 39 more
DTXSID20859077, 6-[(2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-((2-Amino-2-phenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, RefChem:1073645, DTXCID80196632, Alpen, Guicitrine, Ampicin, Wypicil, 6-{[amino(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, Ampen, Semicillin R, MFCD00005175, AB-PC Sol, AB-PC, HI 63, D-(-)-.alpha.-Aminobenzylpenicillin, Ampipenin, nt3, AY 6108, NCGC00018160-02, Pen A Oral, P 50, SQ 17382, .alpha.-Aminobenzylpenicillin, SCHEMBL242460, orb1224219, orb1310268, CHEMBL1617921, D-(-)-.alpha.-Aminopenicillin, CHEBI:94334, BHC17365, BBL016496, STK803647, AKOS000641681, AKOS022060556, 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(2-amino-2-phenyl-acetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, LS-14499, NCI60_004295
- Molecular formula
- C16H19N3O4S
- Empirical formula
- C16H19N3O4S
- Molecular weight
- 349.4 g/mol
- Exact mass
- 349.10963
- CAS number
- 69-53-4
- PubChem CID
- 2174
- Canonical SMILES
- CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
- Isomeric SMILES
- CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
- InChI
- 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)
- InChIKey
- AVKUERGKIZMTKX-UHFFFAOYSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 24
- Rings
- 3
- Aromatic rings
- 1
- Fraction sp³ carbons (Fsp3)
- 0.44
- H-bond donors
- 3
- H-bond acceptors
- 5 computed here · PubChem 6
- Rotatable bonds
- 4
- TPSA (Ų)
- 112.7 computed here · PubChem 138
- Formal charge
- 0
- XLogP3
- -1.1 PubChem
- Complexity
- 562 PubChem
- Stereocenters
- 0 defined, 4 undefinedCIP: C5: undefined · C6: undefined · C10: undefined · C21: undefined
- Double-bond geometry
- None specified
- Point group
- C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C55.00%
- H5.48%
- N12.03%
- O18.32%
- S9.18%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- 0.32 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -2.13 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 3.53 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 349.41
- log P ≤ 5 (Crippen): 0.32
- H-bond donors ≤ 5: 3
- H-bond acceptors ≤ 10: 5
Passes all four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
No GHS hazard classification was found in the sources.
Safety data sheets on the supplier’s page: ChemoSapiens, Clearsynth, AKos Consulting & Solutions.
Always read the supplier’s safety data sheet before working with it.
Spectra
- 13C NMRSpectraBase (Jeol FX-90)
- LC-MSMassBank Europe (Q Exactive Plus Orbitrap Thermo Scientific · LC-ESI-QFT · POSITIVE) · MassBank Europe (Q Exactive Plus Orbitrap Thermo Scientific · LC-ESI-QFT · POSITIVE) · MassBank Europe (Q Exactive Plus Orbitrap Thermo Scientific · LC-ESI-QFT · POSITIVE) · MassBank Europe (Q Exactive Plus Orbitrap Thermo Scientific · LC-ESI-QFT · POSITIVE) · MassBank Europe (Q Exactive Plus Orbitrap Thermo Scientific · LC-ESI-QFT · POSITIVE) · MassBank Europe (Q Exactive Plus Orbitrap Thermo Scientific · LC-ESI-QFT · POSITIVE)
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
- [2]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- [3]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.