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Ampicillin

C16H19N3O4S — CID 6249

💊View drug profile → ampicillin

Data last refreshed: (MolForge compound catalog, from PubChem)

IUPAC(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
SMILESCC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O
InChIInChI=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
InChIKeyAVKUERGKIZMTKX-NJBDSQKTSA-N
MW349.41 g/mol
LogP0.32
Rot. Bonds4

About Ampicillin

Ampicillin (PubChem CID 6249) has the molecular formula C16H19N3O4S and a molecular weight of 349.41 g/mol. Its IUPAC name is (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.

Molecular Properties

Compound NameAmpicillin
PubChem CID6249
Molecular FormulaC16H19N3O4S
Molecular Weight349.41 g/mol
Exact Mass349.11
IUPAC Name(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
SMILESCC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O
InChIInChI=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
InChIKeyAVKUERGKIZMTKX-NJBDSQKTSA-N
XLogP0.32
TPSA112.73 Ų
H-Bond Donors3
H-Bond Acceptors5
Rotatable Bonds4
Heavy Atoms24
Complexity—

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500349.41
LogP ≤ 50.32
H-Bond Donors ≤ 53
H-Bond Acceptors ≤ 105

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Related Compounds

Cephalexin
CID 27447
Penicillin G
CID 5904
Penicillins
CID 2349
Carbenicillin
CID 20824
Mezlocillin
CID 656511
Ampicillin Trihydrate
CID 23565
Penicillin G Potassium
CID 23664709
Penicillin G Sodium
CID 23668834
Azlocillin
CID 6479523

Frequently Asked Questions

What is the IUPAC name of Ampicillin?
The IUPAC name of Ampicillin (CID 6249) is (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.
What is the SMILES notation for Ampicillin?
The canonical SMILES for Ampicillin is CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O.
What is the InChIKey of Ampicillin?
The InChIKey is AVKUERGKIZMTKX-NJBDSQKTSA-N. The full InChI is 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.
What are the key properties of Ampicillin?
Ampicillin has a molecular weight of 349.41 g/mol, XLogP of 0.32, 4 rotatable bonds, 3 hydrogen bond donors, and 5 hydrogen bond acceptors.
Where does this data come from?
All data for Ampicillin is sourced from PubChem (CID 6249), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).

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