Amoxicillin, L-

Details

• Internal ID: c6d1cf54-2555-4768-8d46-54f4a8df34d9
• Taxonomy: Organoheterocyclic compounds > Lactams > Beta lactams > Penams > Penicillins
• IUPAC Name: (2S,5R,6R)-6-[[(2S)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• SMILES (Canonical): CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)C(=O)O)C
• SMILES (Isomeric): 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
• 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)/t9-,10+,11-,14+/m0/s1
• InChI Key: LSQZJLSUYDQPKJ-BBGACYKPSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₉N₃O₅S
• Molecular Weight: 365.40 g/mol
• Exact Mass: 365.10454189 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: -2.00

Synonyms

• Amoxicillin, L-
• 26889-93-0
• (2S,5R,6R)-6-((S)-2-amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 623M8I9SZN
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2S)-amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-amino-2-(p-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-, stereoisomer
• (2S,5R,6R)-6-[[(2S)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (L-Amoxicillin)
• UNII-623M8I9SZN
• CAS-26787-78-0
• Amoxicillin trihydrate impurity B [EP]
• Spectrum_000048
• Spectrum2_000145
• Spectrum3_000300
• Spectrum4_000148
• Spectrum5_000810
• BSPBio_001840
• KBioGR_000596
• KBioSS_000428
• DivK1c_000231
• SPECTRUM1500120
• SPBio_000250
• CHEMBL1367635
• Amoxicillin trihydrate impurity B
• CHEBI:95232
• HMS500L13
• KBio1_000231
• KBio2_000428
• KBio2_002996
• KBio2_005564
• KBio3_001340
• DTXSID30181396
• NINDS_000231
• HMS1920C17
• HMS2091I17
• Pharmakon1600-01500120
• CCG-38922
• NSC755870
• AKOS030238945
• NSC-755870
• IDI1_000231
• NCGC00016797-01
• NCGC00178966-01
• (2S,5R,6R)-6-[[(2S)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(R*)))-
• F83935
• AB00051914_02
• SR-05000001561
• AMOXICILLIN SODIUM IMPURITY B [EP IMPURITY]
• SR-05000001561-1
• AMOXICILLIN TRIHYDRATE IMPURITY B [EP IMPURITY]
• Q27167062
• BENZYLPENICILLIN POTASSIUM IMPURITY C [EP IMPURITY]
• 4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-((AMINO(4-HYDROXYPHENYL)ACETYL)AMINO)-3,3-DIMETHYL-7-OXO-, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.(R*)))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	8.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.17%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.64%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.63%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.03%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.63%	95.56%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	87.73%	85.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.43%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	87.31%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.78%	85.14%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	82.82%	88.81%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.74%	93.10%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	82.26%	90.93%
CHEMBL4208	P20618	Proteasome component C5	81.52%	90.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.40%	94.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.01%	99.15%

Plants that contains it

• Podophyllum peltatum

Cross-Links

• PubChem: 32324
• LOTUS: LTS0138069
• wikiData: Q27167062