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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (3) Show 4 proteins XML

enzymes (1)transporters (3) Show 4 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015193

Secondary Accession Numbers

HMDB0030500
HMDB15193
HMDB30500

Metabolite Identification

Common Name

Amoxicillin

Description

Amoxicillin (International Nonproprietary Name), or amoxycillin (British Approved Name), is a moderate-spectrum, bacteriolytic, -lactam antibiotic used to treat bacterial infections caused by susceptible microorganisms. It is a broad-spectrum semisynthetic antibiotic similar to ampicillin except that its resistance to gastric acid permits higher serum levels with oral administration (PubChem). Amoxicillin is active against a wide range of Gram-positive and a limited range of Gram-negative organisms. It is susceptible to degradation by beta-lactamase-producing bacteria, and so may be given with clavulanic acid to increase its susceptibility. The incidence of beta-lactamase-producing resistant organisms, including E. coli, appears to be increasing. Amoxicillin binds to penicillin-binding protein 1A (PBP-1A) located inside the bacterial cell wall. Penicillins acylate the penicillin-sensitive transpeptidase C-terminal domain by opening the lactam ring. This inactivation of the enzyme prevents the formation of a cross-link of two linear peptidoglycan strands, inhibiting the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that amoxicillin interferes with an autolysin inhibitor. Amoxicillin is usually the drug of choice within the class because it is better absorbed, following oral administration, than other -lactam antibiotics. Amoxicillin in trihydrate form is available as capsules, chewable and dispersible tablets, syrup and pediatric suspension for oral use, and as the sodium salt for intravenous administration. It is one of the most common antibiotics prescribed for children, and the liquid forms are helpful in cases where the patient might find it difficult to take tablets or capsules. It has three ionizable groups. Amoxicillin as a once-daily dosing form (Moxatag) was approved by the American FDA in January 2008. Amoxicillin is one of the semi-synthetic penicillins discovered by Beecham scientists. The patent for amoxicillin has expired, thus amoxicillin is marketed under many trade names, including Actimoxi, Alphamox, AMK, Amoksibos, Amoxiclav Sandoz, Amoxidal, Amoxil, Amoxin, Amoksiklav, Amoxibiotic, Amoxicilina, Apo-Amoxi, Augmentin, Bactox, Betalaktam, Cilamox, Curam, Dedoxil, Dispermox, Duomox, E-Mox (250mg and 500 mg), Enhancin, Gimalxina, Geramox, Hiconcil, Isimoxin, Klavox, Lamoxy, Moxatag, Moxilen, Moxypen, Moxyvit, Nobactam, Novamoxin, Ospamox, Panklav, Pamoxicillin, Panamox, Polymox, Samthongcillin, Clamoxyl, Senox, Sinacilin, Trimox, Tolodina, Wymox, Yucla, Zerrsox, and Zimox. Amoxicillin is found in milk and milk products. It is a potential contaminant in cow's milk arising from its veterinary use.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652312041821292D          

 26 28  0  0  0  0            999 V2000
10011.579010011.3333    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10011.579010010.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.995110009.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.863510011.7459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10010.149010011.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.434310011.7459    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10009.434310012.5710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10006.573910010.0955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.149010010.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10012.404110012.1585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10008.005010011.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.290610011.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.290610010.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.005010010.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.719510010.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.719510011.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.188710011.5887    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10012.404110011.3336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10012.404110010.5088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10013.188710010.2538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10013.673610010.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.306110010.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.306910011.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.443710009.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.891710008.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10014.250510009.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  1  0  0  0
  2  3  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  2  0  0  0  0
  6  7  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
 13  8  1  0  0  0  0
  6 16  1  0  0  0  0
  2  1  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 18  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 17 21  1  0  0  0  0
 20 21  1  0  0  0  0
 20 24  1  6  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 18 10  1  6  0  0  0
 18  1  1  0  0  0  0
  2 19  1  0  0  0  0
M  END

HMDB0015193
     RDKit          3D
Amoxicillin
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.8532    1.8523    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5251    0.5666    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8194    0.8049    1.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4811   -0.4774    1.5827 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1180   -1.7905    0.3582 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7099   -1.8236   -0.1263 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0646   -0.6134    0.1637 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4022   -0.7947    0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8950   -1.9255    0.6401 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2137    0.3969    0.8510 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4466    1.6263    0.6854 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4887    0.4382    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211   -0.0129    0.7738 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8705   -0.0158    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0095    0.4537   -1.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2697    0.4620   -1.7312 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8830    0.9078   -1.7583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6429    0.9029   -1.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3315   -1.6670   -1.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9193   -1.9452   -2.6265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4964   -1.1077   -0.8601 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7099   -0.3630   -0.6864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8319   -1.2868   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9917   -0.8591   -0.3712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6175   -2.6443   -0.5550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6124    2.6616    0.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1861    1.7629   -0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2301    2.1714    1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2047   -0.1155    1.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6102    1.2453    0.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6876    1.5457    2.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5674   -2.7527    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578   -2.7555   -0.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906    0.3270    0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4388    0.3401    1.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638    1.6717    1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0658    2.4417    0.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5665   -0.3903    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7536   -0.3726    0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8044    1.3089   -1.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0005    1.2733   -2.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7558    1.2578   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8683    0.2990   -1.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0367   -3.0046   -1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22  2  1  0
 21  5  1  0
 18 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  5 32  1  1
  6 33  1  6
  7 34  1  0
 10 35  1  1
 11 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 22 43  1  6
 25 44  1  0
M  END


  Mrv1652312041821292D          

 26 28  0  0  0  0            999 V2000
10011.579010011.3333    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10011.579010010.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.995110009.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.863510011.7459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10010.149010011.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.434310011.7459    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10009.434310012.5710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10006.573910010.0955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.149010010.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10012.404110012.1585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10008.005010011.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.290610011.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.290610010.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.005010010.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.719510010.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.719510011.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.188710011.5887    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10012.404110011.3336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10012.404110010.5088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10013.188710010.2538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10013.673610010.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.306110010.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.306910011.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.443710009.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.891710008.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10014.250510009.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  1  0  0  0
  2  3  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  2  0  0  0  0
  6  7  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
 13  8  1  0  0  0  0
  6 16  1  0  0  0  0
  2  1  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 18  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 17 21  1  0  0  0  0
 20 21  1  0  0  0  0
 20 24  1  6  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 18 10  1  6  0  0  0
 18  1  1  0  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015193

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
LSQZJLSUYDQPKJ-NJBDSQKTSA-N

> <FORMULA>
C16H19N3O5S

> <MOLECULAR_WEIGHT>
365.404

> <EXACT_MASS>
365.104541423

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.51793952702992

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5R,6R)-6-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

> <ALOGPS_LOGP>
0.75

> <JCHEM_LOGP>
-2.30806990991309

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.478061495336634

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2314435491785125

> <JCHEM_PKA_STRONGEST_BASIC>
7.221617864505141

> <JCHEM_POLAR_SURFACE_AREA>
132.96

> <JCHEM_REFRACTIVITY>
89.50440000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
amoxicillin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015193
     RDKit          3D
Amoxicillin
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.8532    1.8523    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5251    0.5666    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8194    0.8049    1.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4811   -0.4774    1.5827 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1180   -1.7905    0.3582 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7099   -1.8236   -0.1263 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0646   -0.6134    0.1637 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4022   -0.7947    0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8950   -1.9255    0.6401 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2137    0.3969    0.8510 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4466    1.6263    0.6854 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4887    0.4382    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211   -0.0129    0.7738 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8705   -0.0158    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0095    0.4537   -1.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2697    0.4620   -1.7312 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8830    0.9078   -1.7583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6429    0.9029   -1.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3315   -1.6670   -1.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9193   -1.9452   -2.6265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4964   -1.1077   -0.8601 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7099   -0.3630   -0.6864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8319   -1.2868   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9917   -0.8591   -0.3712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6175   -2.6443   -0.5550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6124    2.6616    0.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1861    1.7629   -0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2301    2.1714    1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2047   -0.1155    1.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6102    1.2453    0.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6876    1.5457    2.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5674   -2.7527    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578   -2.7555   -0.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906    0.3270    0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4388    0.3401    1.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638    1.6717    1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0658    2.4417    0.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5665   -0.3903    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7536   -0.3726    0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8044    1.3089   -1.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0005    1.2733   -2.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7558    1.2578   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8683    0.2990   -1.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0367   -3.0046   -1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22  2  1  0
 21  5  1  0
 18 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  5 32  1  1
  6 33  1  6
  7 34  1  0
 10 35  1  1
 11 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 22 43  1  6
 25 44  1  0
M  END

HEADER    PROTEIN                                 04-DEC-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-DEC-18         0                                  
HETATM    1  C   UNK     0    8688.2818687.822   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8688.2818686.284   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8687.1918685.194   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0    8686.9458688.592   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8685.6118687.822   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8684.2778688.592   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8684.2778690.133   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    8678.9388685.512   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8685.6118686.284   0.000  0.00  0.00           O+0
HETATM   10  H   UNK     0    8689.8218689.363   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0    8681.6098688.593   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8680.2768687.823   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8680.2768686.283   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8681.6098685.513   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8682.9438686.283   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8682.9438687.823   0.000  0.00  0.00           C+0
HETATM   17  S   UNK     0    8691.2868688.299   0.000  0.00  0.00           S+0
HETATM   18  C   UNK     0    8689.8218687.823   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0    8689.8218686.283   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0    8691.2868685.807   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8692.1918687.053   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8693.3718686.064   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8693.3738688.046   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8691.7628684.343   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0    8690.7318683.198   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0    8693.2688684.022   0.000  0.00  0.00           O+0
CONECT    1    4    2   18                                                  
CONECT    2    3    1   19                                                  
CONECT    3    2                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6                                                            
CONECT    8   13                                                            
CONECT    9    5                                                            
CONECT   10   18                                                            
CONECT   11   12   16                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14    8                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11    6                                                  
CONECT   17   18   21                                                       
CONECT   18   19   17   10    1                                             
CONECT   19   18   20    2                                                  
CONECT   20   19   21   24                                                  
CONECT   21   22   23   17   20                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0015193
HETATM    1  C1  UNL     1      -2.853   1.852   0.137  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.525   0.567   0.489  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.819   0.805   1.230  1.00  0.00           C  
HETATM    4  S1  UNL     1      -2.481  -0.477   1.583  1.00  0.00           S  
HETATM    5  C4  UNL     1      -2.118  -1.791   0.358  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.710  -1.824  -0.126  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.065  -0.613   0.164  1.00  0.00           N  
HETATM    8  C6  UNL     1       1.402  -0.795   0.551  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.895  -1.925   0.640  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.214   0.397   0.851  1.00  0.00           C  
HETATM   11  N2  UNL     1       1.447   1.626   0.685  1.00  0.00           N  
HETATM   12  C8  UNL     1       3.489   0.438   0.135  1.00  0.00           C  
HETATM   13  C9  UNL     1       4.621  -0.013   0.774  1.00  0.00           C  
HETATM   14  C10 UNL     1       5.871  -0.016   0.185  1.00  0.00           C  
HETATM   15  C11 UNL     1       6.009   0.454  -1.108  1.00  0.00           C  
HETATM   16  O2  UNL     1       7.270   0.462  -1.731  1.00  0.00           O  
HETATM   17  C12 UNL     1       4.883   0.908  -1.758  1.00  0.00           C  
HETATM   18  C13 UNL     1       3.643   0.903  -1.154  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.332  -1.667  -1.468  1.00  0.00           C  
HETATM   20  O3  UNL     1      -0.919  -1.945  -2.627  1.00  0.00           O  
HETATM   21  N3  UNL     1      -2.496  -1.108  -0.860  1.00  0.00           N  
HETATM   22  C15 UNL     1      -3.710  -0.363  -0.686  1.00  0.00           C  
HETATM   23  C16 UNL     1      -4.832  -1.287  -0.529  1.00  0.00           C  
HETATM   24  O4  UNL     1      -5.992  -0.859  -0.371  1.00  0.00           O  
HETATM   25  O5  UNL     1      -4.617  -2.644  -0.555  1.00  0.00           O  
HETATM   26  H1  UNL     1      -3.612   2.662   0.003  1.00  0.00           H  
HETATM   27  H2  UNL     1      -2.186   1.763  -0.751  1.00  0.00           H  
HETATM   28  H3  UNL     1      -2.230   2.171   1.018  1.00  0.00           H  
HETATM   29  H4  UNL     1      -5.205  -0.116   1.697  1.00  0.00           H  
HETATM   30  H5  UNL     1      -5.610   1.245   0.562  1.00  0.00           H  
HETATM   31  H6  UNL     1      -4.688   1.546   2.039  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.567  -2.753   0.559  1.00  0.00           H  
HETATM   33  H8  UNL     1      -0.158  -2.756  -0.011  1.00  0.00           H  
HETATM   34  H9  UNL     1      -0.391   0.327   0.076  1.00  0.00           H  
HETATM   35  H10 UNL     1       2.439   0.340   1.954  1.00  0.00           H  
HETATM   36  H11 UNL     1       0.764   1.672   1.495  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.066   2.442   0.761  1.00  0.00           H  
HETATM   38  H13 UNL     1       4.567  -0.390   1.787  1.00  0.00           H  
HETATM   39  H14 UNL     1       6.754  -0.373   0.697  1.00  0.00           H  
HETATM   40  H15 UNL     1       7.804   1.309  -1.596  1.00  0.00           H  
HETATM   41  H16 UNL     1       5.000   1.273  -2.770  1.00  0.00           H  
HETATM   42  H17 UNL     1       2.756   1.258  -1.659  1.00  0.00           H  
HETATM   43  H18 UNL     1      -3.868   0.299  -1.563  1.00  0.00           H  
HETATM   44  H19 UNL     1      -4.037  -3.005  -1.324  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4   22
CONECT    3   29   30   31
CONECT    4    5
CONECT    5    6   21   32
CONECT    6    7   19   33
CONECT    7    8   34
CONECT    8    9    9   10
CONECT   10   11   12   35
CONECT   11   36   37
CONECT   12   13   13   18
CONECT   13   14   38
CONECT   14   15   15   39
CONECT   15   16   17
CONECT   16   40
CONECT   17   18   18   41
CONECT   18   42
CONECT   19   20   20   21
CONECT   21   22
CONECT   22   23   43
CONECT   23   24   24   25
CONECT   25   44
END

HMDB0015193
     RDKit          3D
Amoxicillin
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.8532    1.8523    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5251    0.5666    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8194    0.8049    1.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4811   -0.4774    1.5827 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1180   -1.7905    0.3582 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7099   -1.8236   -0.1263 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0646   -0.6134    0.1637 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4022   -0.7947    0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8950   -1.9255    0.6401 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2137    0.3969    0.8510 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4466    1.6263    0.6854 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4887    0.4382    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211   -0.0129    0.7738 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8705   -0.0158    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0095    0.4537   -1.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2697    0.4620   -1.7312 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8830    0.9078   -1.7583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6429    0.9029   -1.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3315   -1.6670   -1.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9193   -1.9452   -2.6265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4964   -1.1077   -0.8601 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7099   -0.3630   -0.6864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8319   -1.2868   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9917   -0.8591   -0.3712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6175   -2.6443   -0.5550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6124    2.6616    0.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1861    1.7629   -0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2301    2.1714    1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2047   -0.1155    1.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6102    1.2453    0.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6876    1.5457    2.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5674   -2.7527    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578   -2.7555   -0.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906    0.3270    0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4388    0.3401    1.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638    1.6717    1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0658    2.4417    0.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5665   -0.3903    1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7536   -0.3726    0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8044    1.3089   -1.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0005    1.2733   -2.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7558    1.2578   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8683    0.2990   -1.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0367   -3.0046   -1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22  2  1  0
 21  5  1  0
 18 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  5 32  1  1
  6 33  1  6
  7 34  1  0
 10 35  1  1
 11 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 22 43  1  6
 25 44  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(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	ChEBI
6-(p-Hydroxy-alpha-aminophenylacetamido)penicillanic acid	ChEBI
alpha-Amino-p-hydroxybenzylpenicillin	ChEBI
Amolin	ChEBI
Amopenixin	ChEBI
Amoxicilina	ChEBI
Amoxicillin anhydrous	ChEBI
Amoxicilline	ChEBI
Amoxicillinum	ChEBI
Amoxycilin	ChEBI
Amoxycillin	ChEBI
AMPC	ChEBI
AX	ChEBI
Clamoxyl	ChEBI
Moxal	ChEBI
p-Hydroxyampicillin	ChEBI
(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-carboxylate	Generator
6-(p-Hydroxy-a-aminophenylacetamido)penicillanate	Generator
6-(p-Hydroxy-a-aminophenylacetamido)penicillanic acid	Generator
6-(p-Hydroxy-alpha-aminophenylacetamido)penicillanate	Generator
6-(p-Hydroxy-α-aminophenylacetamido)penicillanate	Generator
6-(p-Hydroxy-α-aminophenylacetamido)penicillanic acid	Generator
a-Amino-p-hydroxybenzylpenicillin	Generator
Α-amino-p-hydroxybenzylpenicillin	Generator
Amoxicillin trihydrate	HMDB
Amoxycillin trihydrate	HMDB
D-Amoxicillin	HMDB
Actimoxi	HMDB
Amoxicillin monopotassium salt	HMDB
Amoxicillin monosodium salt	HMDB
Clariana brand OF amoxicillin	HMDB
Polymox	HMDB
Amoxicillin sodium	HMDB
Clamoxyl parenteral	HMDB
Trihydrate, amoxicillin	HMDB
Anhydrous, amoxicillin	HMDB
Clamoxyl g.a.	HMDB
Hydroxyampicillin	HMDB
Pfizer brand OF amoxicillin sodium salt	HMDB
Trimox	HMDB
Wymox	HMDB
Amoxicillin clariana brand	HMDB
Amoxicillin, (r*)-isomer	HMDB
Amoxil	HMDB
G.A., clamoxyl	HMDB
Penamox	HMDB
SmithKline beecham brand OF amoxicillin sodium salt	HMDB
Sodium, amoxicillin	HMDB
Parenteral, clamoxyl	HMDB
6-(a-Amino-4-hydroxyphenylacetamido)penicillanic acid	HMDB
6-(D-(-)-p-Hydroxy-alpha-aminobenzyl)penicillin	HMDB
6-[[Amino(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 9ci	HMDB
Almodan	HMDB
Amix	HMDB
Amoclen	HMDB
Amopen	HMDB
Amoram	HMDB
Amox 250 cap 250MG	HMDB
Amox 500 cap 500MG	HMDB
Amox S 125 sus 125mg/5ML	HMDB
Amox S 250 sus 250mg/5ML	HMDB
Amoxi	HMDB
Amoxi-mast	HMDB
Amoxicaps	HMDB
Amoxicillin (anhydrous)	HMDB
Amoxicillin and clavulanate potassium	HMDB
Amoxicillin pediatric	HMDB
Amoxicillin(usan)	HMDB
Amoxid	HMDB
Amoxiden	HMDB
Amoxivet	HMDB
Amoxycillin, ban	HMDB
Amoxymed	HMDB
Amrit	HMDB
Anemolin	HMDB
Apo-amoxi	HMDB
Apo-amoxi cap 250MG	HMDB
Apo-amoxi cap 500MG	HMDB
Apo-amoxi PWR for susp 125mg/5ML	HMDB
Apo-amoxi PWR for susp 250mg/5ML	HMDB
Apo-amoxi sugar free	HMDB
Aspenil	HMDB
AUGMENTIN '125'	HMDB
AUGMENTIN '200'	HMDB
AUGMENTIN '250'	HMDB
AUGMENTIN '400'	HMDB
AUGMENTIN '500'	HMDB
AUGMENTIN '875'	HMDB
AUGMENTIN es-600	HMDB
Biomox	HMDB
Bristamox	HMDB
BRL 2333	HMDB
Cemoxin	HMDB
Clamoxyl (SKB)	HMDB
D-(-)-alpha-Amino-p-hydroxybenzyl penicillin	HMDB
D-(-)-alpha-Amino-p-hydroxybenzylpenicillin	HMDB
D-(alpha-Amino-p-hydroxybenzyl)penicillin	HMDB
D-2-Amino-2-(4-hydroxyphenyl)acetamidopenicillanic acid	HMDB
Delacillin	HMDB
Dispermox	HMDB
Efpenix	HMDB
Flemoxin	HMDB
Galenamox	HMDB
Gen-amoxicillin 250MG	HMDB
Gen-amoxicillin 500MG	HMDB
Hiconcil	HMDB
Histocillin	HMDB
Ibiamox	HMDB
Imacillin	HMDB
Larotid	HMDB
Metafarma capsules	HMDB
Metifarma capsules	HMDB
Moxacin	HMDB
Moxatag	HMDB
Novamoxin cap 250MG	HMDB
Novamoxin cap 500MG	HMDB
Novamoxin sus 125mg/5ML	HMDB
Novamoxin sus 250mg/5ML	HMDB
Nu-amoxi cap 250MG	HMDB
Nu-amoxi cap 500MG	HMDB
Nu-amoxi sus 125/5ML	HMDB
Nu-amoxi sus 250mg/5ML	HMDB
Ospamox	HMDB
PHL-Amoxicillin	HMDB
Piramox	HMDB
PMS-Amoxicillin	HMDB
Prevpac	HMDB
Pro amox PWR for oral susp 125mg/5ML	HMDB
Pro amox-250 cap 250MG	HMDB
Pro amox-500 cap 500MG	HMDB
Pro-amox-250 orl sus 250mg/5ML	HMDB
R-Hydroxyampicillin	HMDB
Rimoxallin	HMDB
Robamox	HMDB
Sauracillin	HMDB
Sawamox PM	HMDB
Sumox	HMDB
Unicillin	HMDB
Utimox	HMDB
Vetramox	HMDB
Amoxicillin	HMDB

Chemical Formula

C₁₆H₁₉N₃O₅S

Average Molecular Weight

365.404

Monoisotopic Molecular Weight

365.104541423

IUPAC Name

(2S,5R,6R)-6-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

amoxicillin

CAS Registry Number

26787-78-0

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=C(O)C=C1)C(O)=O

InChI Identifier

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

InChI Key

LSQZJLSUYDQPKJ-NJBDSQKTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Penicillins

Alternative Parents

Substituents

Penicillin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Phenylacetamide
Phenol
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Monocyclic benzene moiety
Thiazolidine
Tertiary carboxylic acid amide
Azetidine
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Amino acid
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Dialkylthioether
Hemithioaminal
Thioether
Primary aliphatic amine
Amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:2676 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0015193)

Source

Exogenous

Exogenous (HMDB: HMDB0015193)

Food

Food (HMDB: HMDB0015193)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Milk and milk products (FooDB: FOOD00863)

Endogenous

Endogenous (HMDB: HMDB0015193)

Animal

Animal (HMDB: HMDB0015193)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antimicrobial agent (HMDB: HMDB0015193)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	194 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.96 g/L	Not Available
LogP	0	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	187.388	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000941

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.96 g/L	ALOGPS
logP	0.75	ALOGPS
logP	-2.3	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.23	ChemAxon
pKa (Strongest Basic)	7.22	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.96 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	89.5 m³·mol⁻¹	ChemAxon
Polarizability	35.52 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	182.047	31661259
DarkChem	[M-H]-	174.579	31661259
DeepCCS	[M-2H]-	215.063	30932474
DeepCCS	[M+Na]+	190.473	30932474
AllCCS	[M+H]+	180.4	32859911
AllCCS	[M+H-H2O]+	177.9	32859911
AllCCS	[M+NH4]+	182.7	32859911
AllCCS	[M+Na]+	183.4	32859911
AllCCS	[M-H]-	181.9	32859911
AllCCS	[M+Na-2H]-	181.9	32859911
AllCCS	[M+HCOO]-	182.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.96 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3425 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.04 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	291.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1322.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	188.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	99.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	146.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	56.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	286.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	307.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	524.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	636.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	284.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	976.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	206.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	223.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	324.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	437.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	203.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Amoxicillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=C(O)C=C1)C(O)=O	4424.5	Standard polar	33892256
Amoxicillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=C(O)C=C1)C(O)=O	2614.9	Standard non polar	33892256
Amoxicillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=C(O)C=C1)C(O)=O	3442.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Amoxicillin,1TMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=C(O[Si](C)(C)C)C=C3)C(=O)N2[C@H]1C(=O)O	3139.2	Semi standard non polar	33892256
Amoxicillin,1TMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=C(O)C=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3006.7	Semi standard non polar	33892256
Amoxicillin,1TMS,isomer #3	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=C(O)C=C3)C(=O)N2[C@H]1C(=O)O	3097.3	Semi standard non polar	33892256
Amoxicillin,1TMS,isomer #4	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=C(O)C=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	2969.7	Semi standard non polar	33892256
Amoxicillin,2TMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=C(O[Si](C)(C)C)C=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3106.8	Semi standard non polar	33892256
Amoxicillin,2TMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C3)C(=O)N2[C@H]1C(=O)O	3128.3	Semi standard non polar	33892256
Amoxicillin,2TMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=C(O[Si](C)(C)C)C=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	3053.2	Semi standard non polar	33892256
Amoxicillin,2TMS,isomer #4	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=C(O)C=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3017.5	Semi standard non polar	33892256
Amoxicillin,2TMS,isomer #5	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=C(O)C=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2931.1	Semi standard non polar	33892256
Amoxicillin,2TMS,isomer #6	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=C(O)C=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	3013.0	Semi standard non polar	33892256
Amoxicillin,2TMS,isomer #7	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	3083.1	Semi standard non polar	33892256
Amoxicillin,3TMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3109.6	Semi standard non polar	33892256
Amoxicillin,3TMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2984.3	Standard non polar	33892256
Amoxicillin,3TMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3937.6	Standard polar	33892256
Amoxicillin,3TMS,isomer #2	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=C(O[Si](C)(C)C)C=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3051.4	Semi standard non polar	33892256
Amoxicillin,3TMS,isomer #2	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=C(O[Si](C)(C)C)C=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2984.0	Standard non polar	33892256
Amoxicillin,3TMS,isomer #2	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=C(O[Si](C)(C)C)C=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	4093.9	Standard polar	33892256
Amoxicillin,3TMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	3073.0	Semi standard non polar	33892256
Amoxicillin,3TMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	3031.5	Standard non polar	33892256
Amoxicillin,3TMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	3859.4	Standard polar	33892256
Amoxicillin,3TMS,isomer #4	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	3137.6	Semi standard non polar	33892256
Amoxicillin,3TMS,isomer #4	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	3093.0	Standard non polar	33892256
Amoxicillin,3TMS,isomer #4	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	4012.2	Standard polar	33892256
Amoxicillin,3TMS,isomer #5	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=C(O)C=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2988.6	Semi standard non polar	33892256
Amoxicillin,3TMS,isomer #5	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=C(O)C=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3063.7	Standard non polar	33892256
Amoxicillin,3TMS,isomer #5	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=C(O)C=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3783.8	Standard polar	33892256
Amoxicillin,3TMS,isomer #6	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3037.6	Semi standard non polar	33892256
Amoxicillin,3TMS,isomer #6	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3119.0	Standard non polar	33892256
Amoxicillin,3TMS,isomer #6	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	4042.7	Standard polar	33892256
Amoxicillin,3TMS,isomer #7	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	3063.2	Semi standard non polar	33892256
Amoxicillin,3TMS,isomer #7	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	3175.4	Standard non polar	33892256
Amoxicillin,3TMS,isomer #7	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	3983.9	Standard polar	33892256
Amoxicillin,4TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3086.8	Semi standard non polar	33892256
Amoxicillin,4TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3045.0	Standard non polar	33892256
Amoxicillin,4TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3500.5	Standard polar	33892256
Amoxicillin,4TMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3143.3	Semi standard non polar	33892256
Amoxicillin,4TMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3105.9	Standard non polar	33892256
Amoxicillin,4TMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3693.2	Standard polar	33892256
Amoxicillin,4TMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	3131.0	Semi standard non polar	33892256
Amoxicillin,4TMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	3168.0	Standard non polar	33892256
Amoxicillin,4TMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	3660.6	Standard polar	33892256
Amoxicillin,4TMS,isomer #4	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3052.0	Semi standard non polar	33892256
Amoxicillin,4TMS,isomer #4	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3196.2	Standard non polar	33892256
Amoxicillin,4TMS,isomer #4	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3576.8	Standard polar	33892256
Amoxicillin,5TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3163.5	Semi standard non polar	33892256
Amoxicillin,5TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3165.7	Standard non polar	33892256
Amoxicillin,5TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3355.7	Standard polar	33892256
Amoxicillin,1TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C(=O)N2[C@H]1C(=O)O	3374.5	Semi standard non polar	33892256
Amoxicillin,1TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=C(O)C=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3289.3	Semi standard non polar	33892256
Amoxicillin,1TBDMS,isomer #3	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C3)C(=O)N2[C@H]1C(=O)O	3317.4	Semi standard non polar	33892256
Amoxicillin,1TBDMS,isomer #4	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=C(O)C=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3240.5	Semi standard non polar	33892256
Amoxicillin,2TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3576.8	Semi standard non polar	33892256
Amoxicillin,2TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C(=O)N2[C@H]1C(=O)O	3581.9	Semi standard non polar	33892256
Amoxicillin,2TBDMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3517.7	Semi standard non polar	33892256
Amoxicillin,2TBDMS,isomer #4	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3481.1	Semi standard non polar	33892256
Amoxicillin,2TBDMS,isomer #5	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=C(O)C=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3418.3	Semi standard non polar	33892256
Amoxicillin,2TBDMS,isomer #6	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3445.4	Semi standard non polar	33892256
Amoxicillin,2TBDMS,isomer #7	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3607.4	Semi standard non polar	33892256
Amoxicillin,3TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3750.3	Semi standard non polar	33892256
Amoxicillin,3TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3621.5	Standard non polar	33892256
Amoxicillin,3TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	4082.9	Standard polar	33892256
Amoxicillin,3TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3688.9	Semi standard non polar	33892256
Amoxicillin,3TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3591.8	Standard non polar	33892256
Amoxicillin,3TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	4230.3	Standard polar	33892256
Amoxicillin,3TBDMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3721.3	Semi standard non polar	33892256
Amoxicillin,3TBDMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3658.8	Standard non polar	33892256
Amoxicillin,3TBDMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	4044.6	Standard polar	33892256
Amoxicillin,3TBDMS,isomer #4	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3862.8	Semi standard non polar	33892256
Amoxicillin,3TBDMS,isomer #4	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3685.6	Standard non polar	33892256
Amoxicillin,3TBDMS,isomer #4	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	4132.4	Standard polar	33892256
Amoxicillin,3TBDMS,isomer #5	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3609.3	Semi standard non polar	33892256
Amoxicillin,3TBDMS,isomer #5	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3700.3	Standard non polar	33892256
Amoxicillin,3TBDMS,isomer #5	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3941.9	Standard polar	33892256
Amoxicillin,3TBDMS,isomer #6	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3754.6	Semi standard non polar	33892256
Amoxicillin,3TBDMS,isomer #6	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3720.6	Standard non polar	33892256
Amoxicillin,3TBDMS,isomer #6	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	4098.1	Standard polar	33892256
Amoxicillin,3TBDMS,isomer #7	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3773.6	Semi standard non polar	33892256
Amoxicillin,3TBDMS,isomer #7	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3760.7	Standard non polar	33892256
Amoxicillin,3TBDMS,isomer #7	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	4082.6	Standard polar	33892256
Amoxicillin,4TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3875.3	Semi standard non polar	33892256
Amoxicillin,4TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3810.3	Standard non polar	33892256
Amoxicillin,4TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3822.3	Standard polar	33892256
Amoxicillin,4TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	4001.8	Semi standard non polar	33892256
Amoxicillin,4TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3844.3	Standard non polar	33892256
Amoxicillin,4TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3911.8	Standard polar	33892256
Amoxicillin,4TBDMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	4005.3	Semi standard non polar	33892256
Amoxicillin,4TBDMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3906.1	Standard non polar	33892256
Amoxicillin,4TBDMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3904.8	Standard polar	33892256
Amoxicillin,4TBDMS,isomer #4	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3915.4	Semi standard non polar	33892256
Amoxicillin,4TBDMS,isomer #4	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3953.7	Standard non polar	33892256
Amoxicillin,4TBDMS,isomer #4	CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=C(O)C=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3814.2	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01060	21059682	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01060	21059682	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01060

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

31006

KEGG Compound ID

C06827

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amoxicillin

METLIN ID

Not Available

PubChem Compound

33613

PDB ID

Not Available

ChEBI ID

2676

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Adams OP, Levett PN, Cruickshank JK, Prussia PR, Garriques SA, Cooper RE: Necrotizing haemorrhagic colitis caused by resistant Shigella flexneri. Report of a case. West Indian Med J. 1993 Jun;42(2):85-6. [PubMed:8367972 ]
Mehta A, Chopra S, Mehta P: Antibiotic inhibition of pectolytic and cellulolytic enzyme activity in two Fusarium species. Mycopathologia. 1993 Dec;124(3):185-8. [PubMed:8022465 ]
Drawz SM, Bonomo RA: Three decades of beta-lactamase inhibitors. Clin Microbiol Rev. 2010 Jan;23(1):160-201. doi: 10.1128/CMR.00037-09. [PubMed:20065329 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. Solute carrier family 15 member 1

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:: SLC15A1
Uniprot ID:: P46059
Molecular weight:: 78805.3

References

Wenzel U, Gebert I, Weintraut H, Weber WM, Clauss W, Daniel H: Transport characteristics of differently charged cephalosporin antibiotics in oocytes expressing the cloned intestinal peptide transporter PepT1 and in human intestinal Caco-2 cells. J Pharmacol Exp Ther. 1996 May;277(2):831-9. [PubMed:8627565 ]
Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]
Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]

Enzyme Details

2. Solute carrier family 15 member 2

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:: SLC15A2
Uniprot ID:: Q16348
Molecular weight:: 81782.8

References

Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]
Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]

Enzyme Details

3. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577 ]

Showing metabocard for Amoxicillin (HMDB0015193)

MOL for HMDB0015193 (Amoxicillin)

3D MOL for HMDB0015193 (Amoxicillin)

3D SDF for HMDB0015193 (Amoxicillin)

3D-SDF for HMDB0015193 (Amoxicillin)

PDB for HMDB0015193 (Amoxicillin)

3D PDB for HMDB0015193 (Amoxicillin)

SMILES for HMDB0015193 (Amoxicillin)

INCHI for HMDB0015193 (Amoxicillin)

Structure for HMDB0015193 (Amoxicillin)

3D Structure for HMDB0015193 (Amoxicillin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

Transporters

References

References

References