Amoxicillin

C16H19N3O5S — CID 33613

IUPAC(2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILESCC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)C(=O)O)C
InChIInChI=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)/t9-,10-,11+,14-/m1/s1
InChIKeyLSQZJLSUYDQPKJ-NJBDSQKTSA-N
MW365.40 g/mol
LogP-2.00
Rot. Bonds4

About Amoxicillin

Amoxicillin (PubChem CID 33613) has the molecular formula C16H19N3O5S and a molecular weight of 365.40 g/mol. Its IUPAC name is (2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid.

Molecular Properties

Compound NameAmoxicillin
PubChem CID33613
Molecular FormulaC16H19N3O5S
Molecular Weight365.40 g/mol
Exact Mass365.10
IUPAC Name(2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILESCC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)C(=O)O)C
InChIInChI=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)/t9-,10-,11+,14-/m1/s1
InChIKeyLSQZJLSUYDQPKJ-NJBDSQKTSA-N
XLogP-2.00
TPSA158.00 Ų
H-Bond Donors4
H-Bond Acceptors7
Rotatable Bonds4
Heavy Atoms25
Complexity590

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500365.40
LogP ≤ 5-2.00
H-Bond Donors ≤ 54
H-Bond Acceptors ≤ 107

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Related Compounds

Ampicillin
CID 6249
Cefadroxil
CID 47965
Ampicillin Trihydrate
CID 23565
Cefprozil
CID 62977
Amoxicillin Trihydrate
CID 62883
Aspoxicillin
CID 71961
Amoxicillin mixture with Clavulanate
CID 6435924
Cefadroxil Monohydrate
CID 47964
Cefprozil Anhydrous, (Z)-
CID 5284528
Procef
CID 5281006
Amoxicillin, L-
CID 32324
(2S,5R,6R)-6-((2-(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
CID 120720

Frequently Asked Questions

What is the IUPAC name of Amoxicillin?
The IUPAC name of Amoxicillin (CID 33613) is (2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid.
What is the SMILES notation for Amoxicillin?
The canonical SMILES for Amoxicillin is CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)C(=O)O)C.
What is the InChIKey of Amoxicillin?
The InChIKey is LSQZJLSUYDQPKJ-NJBDSQKTSA-N. The full InChI is 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)/t9-,10-,11+,14-/m1/s1.
What are the key properties of Amoxicillin?
Amoxicillin has a molecular weight of 365.40 g/mol, XLogP of -2.00, 4 rotatable bonds, 4 hydrogen bond donors, and 7 hydrogen bond acceptors.
Where does this data come from?
All data for Amoxicillin is sourced from PubChem (CID 33613), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).