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Amoxicillin

Athanor · official

C16H19N3O5S · 365.4 g/mol

IUPAC name: 6-[[2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Also called Amoxil, Augmentin, beta-lactam

Drugs
Open in Athanor
The structure of Amoxicillin
Drawn from its SMILES with RDKit

Names and identifiers

IUPAC name
6-[[2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Synonyms
Amoxil, Augmentin, beta-lactam
+ 38 more

DTXSID50860378, 6-(2-Amino(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-[2-Amino(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, RefChem:1073671, DTXCID50196700, 6-[2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, Amoxicillin (trihydrate), Amoxycillin (trihydrate), 6-{[amino(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, Amoxicillin-13C2,15N(MixtureofDiastereomers), Amoxicillin-13C2,15N, SCHEMBL226659, orb1225468, HMS3372L05, HMS5081K04, HEC00299, MFCD00126985, s3015, STL140785, AKOS005715796, .alpha.-Amino-p-hydroxybenzylpenicillin, 6-[[2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, AC-15069, DB-015558, D-(.alpha.-Amino-p-hydroxybenzyl)penicillin, NS00008883, ST50999667, D-(-)-.alpha.-Amino-p-hydroxybenzylpenicillin, EN300-296143, D-(-)-.alpha.-Amino-p-hydroxybenzyl penicillin, WLN: T45 ANV ESTJ CMVYZR DQ& F1 F1 GVQ, 6-[D-(-)-p-Hydroxy-.alpha.-aminobenzyl]penicillin, 6-(p-Hydroxy-.alpha.-aminophenylacetamido)penicillanic acid, 6[D(-).alpha.-Amino-p-hydroxyphenylacetamido]penicillanic acid, 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3-dimethyl-7-oxo- [2S[2.alpha.,5.alpha.,6.beta.(S*)]], 6-(2-amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid, 6-[2-amino-2-(4-hydroxyphenyl)acetylamino]-3,3-dimethyl-7-oxo-4-thia-1-azabicy clo[3.2.0]heptane-2-carboxylic acid, 6-[D-(-)-2-Amino-2-(p-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Molecular formula
C16H19N3O5S
Empirical formula
C16H19N3O5S
Molecular weight
365.4 g/mol
Exact mass
365.10454
CAS number
26787-78-0
PubChem CID
2171
Canonical SMILES
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)C(=O)O)C
Isomeric SMILES
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)C(=O)O)C
InChI
InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)
InChIKey
LSQZJLSUYDQPKJ-UHFFFAOYSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms
25
Rings
3
Aromatic rings
1
Fraction sp³ carbons (Fsp3)
0.44
H-bond donors
4
H-bond acceptors
6 computed here · PubChem 7
Rotatable bonds
4
TPSA (Ų)
133 computed here · PubChem 158
Formal charge
0
XLogP3
-2 PubChem
Complexity
590 PubChem
Stereocenters
0 defined, 4 undefinedCIP: C5: undefined · C6: undefined · C10: undefined · C22: 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

  • C52.59%
  • H5.24%
  • N11.50%
  • O21.89%
  • S8.78%

Isotope pattern

100%365.10420%366.1077.4%367.1041.2%368.106369.106

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
0.02 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-2.03 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
3.66 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 365.41
  • log P ≤ 5 (Crippen): 0.02
  • H-bond donors ≤ 5: 4
  • H-bond acceptors ≤ 10: 6

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: Clearsynth, Amerigo Scientific, Biorbyt.

Always read the supplier’s safety data sheet before working with it.

Spectra

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. [1]NMRShiftDB · Linked only · via PubChem · retrieved 2026-10-14
  2. [2]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  3. [3]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  4. [4]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  5. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  6. ·Literature on PubChem

Data last updated 2026-10-14.