NP-MRD: Showing NP-Card for (2s,5r,6r)-6-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (NP0241885)

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Record Information

Version

2.0

Created at

2022-09-07 02:04:26 UTC

Updated at

2022-09-07 02:04:27 UTC

NP-MRD ID

NP0241885

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,5r,6r)-6-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Description

Amoxicillin, also known as clamoxyl or amopenixin, 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]. A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group. (2s,5r,6r)-6-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is found in Apis cerana and Arundo donax. (2s,5r,6r)-6-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid was first documented in 1993 (PMID: 8367972). Amoxicillin is a very strong basic compound (based on its pKa) (PMID: 8022465) (PMID: 20065329).

Structure

MOL 3D MOL SDF 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

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
   -4.7595   -0.3575    1.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5506    0.1987    0.9595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0533    1.4265    1.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2777   -1.1118    0.9074 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0570   -1.1422   -0.9102 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6682   -0.7810   -1.3724 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1935   -0.4233   -0.2980 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4446   -1.0600   -0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8045   -1.9423   -0.9658 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665   -0.7121    0.9546 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8376    0.3098    1.8154 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6299   -0.1931    0.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7728   -0.9617    0.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9516   -0.4754   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9640    0.8196   -0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0933    1.3878   -1.3018 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8274    1.5962   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6445    1.0961   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3868    0.3403   -2.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0249    1.0989   -2.9828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5296    0.1945   -1.2086 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7570    0.4632   -0.5188 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8352   -0.3412   -1.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0292   -0.3376   -0.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5637   -1.1663   -2.1803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5391   -0.3598    2.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6582    0.2932    1.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669   -1.4187    1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9267    2.0847    1.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5895    1.2256    2.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566    2.0216    1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5340   -1.9797   -1.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2829   -1.5652   -2.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0937    0.3052    0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5879   -1.6071    1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110    1.0704    2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3319   -0.0426    2.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7583   -1.9616    0.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8505   -1.0741   -0.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2780    1.3123   -2.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7866    2.6232   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7526    1.7059   -0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0293    1.5434   -0.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9175   -2.1026   -2.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  2 22  1  0
 22 21  1  0
 21 19  1  0
 19 20  2  0
 19  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
 22 23  1  0
 23 25  1  0
 23 24  2  0
 21  5  1  0
 18 12  1  0
  6  5  1  0
  5 32  1  6
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
 22 43  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
 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>
NP0241885

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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 Mass

365.4040 Da

Monoisotopic Mass

365.10454 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Arundo donax	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0015193

DrugBank ID

DB01060

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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. doi: 10.1007/BF01103736. [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 ]
LOTUS database [Link]

Showing NP-Card for (2s,5r,6r)-6-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (NP0241885)

MOL for NP0241885 ((2s,5r,6r)-6-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D MOL for NP0241885 ((2s,5r,6r)-6-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D SDF for NP0241885 ((2s,5r,6r)-6-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D-SDF for NP0241885 ((2s,5r,6r)-6-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

PDB for NP0241885 ((2s,5r,6r)-6-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D PDB for NP0241885 ((2s,5r,6r)-6-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

SMILES for NP0241885 ((2s,5r,6r)-6-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

INCHI for NP0241885 ((2s,5r,6r)-6-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

Structure for NP0241885 ((2s,5r,6r)-6-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D Structure for NP0241885 ((2s,5r,6r)-6-{[(2r)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)