NP-MRD: Showing NP-Card for (2r)-2-amino-n-[(2s,5r,6r)-2-({1-[(ethoxycarbonyl)oxy]ethoxy}carbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylethanimidic acid (NP0267401)

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Record Information

Version

2.0

Created at

2022-09-08 12:10:25 UTC

Updated at

2022-09-08 12:10:25 UTC

NP-MRD ID

NP0267401

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-2-amino-n-[(2s,5r,6r)-2-({1-[(ethoxycarbonyl)oxy]ethoxy}carbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylethanimidic acid

Description

Bacampicillin, also known as BAPC or penglobe, belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine. Bacampicillin is a drug which is used for infections at the following sites: Upper and lower respiratory tract; skin and soft tissue; urinary tract and acute uncomplicated gonococcal urethritis, when due to sensitive strains of the following organisms: Gram-positive: Streptococci (including s. Faecalis and s. Pneumoniae) and nonpenicillinase-producing staphylococci; gram-negative: h. Influenzae, n. Gonorrhoeae, e. Coli, p. Mirabilis, salmonellae and shigellae. Bacampicillin is a very strong basic compound (based on its pKa). (2r)-2-amino-n-[(2s,5r,6r)-2-({1-[(ethoxycarbonyl)oxy]ethoxy}carbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylethanimidic acid is found in Apis cerana. (2r)-2-amino-n-[(2s,5r,6r)-2-({1-[(ethoxycarbonyl)oxy]ethoxy}carbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylethanimidic acid was first documented in 1975 (PMID: 1211909). A penicillanic acid ester that is the 1-ethoxycarbonyloxyethyl ester of ampicillin (PMID: 464583) (PMID: 7012993) (PMID: 7012998).

Structure

MOL 3D MOL SDF PDB SMILES InChI

1602
  Mrv0541 02231215352D          

 33 35  0  0  1  0            999 V2000
    7.6202    2.5306    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215    0.8626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3231   -0.2020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6820    0.2396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4090    1.8553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0259   -1.5998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7288   -2.9975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0879   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8355    1.4506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215    2.8637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572    4.0328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8355    2.2756    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1050    1.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6202    1.1957    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0037    2.2791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0037    1.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7725    2.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7725    1.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8751    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6242    2.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0420    3.2363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5780   -0.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2447    3.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3849   -1.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0295    2.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625    3.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2322    2.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8652    3.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2809   -2.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9838   -3.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4317   -4.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7336    2.9278    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  2 16  2  0  0  0  0
  3 19  1  0  0  0  0
  3 22  1  0  0  0  0
  4 19  2  0  0  0  0
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 27 30  2  0  0  0  0
 28 30  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
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    7.8999    1.8876    0.9604 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5162    2.0741    1.0996 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1104   -0.1032    1.7255 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3323    1.3066    1.5971 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3729    0.3637    1.9745 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.1184   -1.1215   -0.6899 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4670    0.1168   -1.0640 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.2826   -1.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4582    1.8954   -2.7427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1374    1.4959   -0.8610 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4060    1.0466   -1.3361 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6036    1.8015   -1.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5351    2.9370   -0.7302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8867    1.3160   -1.7496 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8971    2.3306   -1.5312 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3608    0.0880   -1.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8763    0.2521    0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3553   -0.7821    0.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3082   -2.0542    0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8002   -2.2291   -0.8471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3256   -1.1639   -1.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3886    0.5661    0.0500 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2283   -1.0304    0.3894 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0540   -2.1192   -0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4984   -2.8206   -1.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4842   -3.1630    0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5683   -0.1137    0.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0093    1.1873   -0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2613    0.6165   -0.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3598    2.8555    0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3820    1.5282    1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8286   -0.6282    2.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4044    1.8400    3.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6426    0.2331    3.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1432    0.3794    4.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6533   -1.4922   -1.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2074    2.5047   -0.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4624    0.1007   -1.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8899    1.0979   -2.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0754    2.9008   -2.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5624    2.9883   -0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9244    1.2479    0.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7595   -0.6461    1.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6838   -2.8979    1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7594   -3.2267   -1.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9212   -1.2927   -2.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1344    1.0076    0.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1012   -3.6896   -1.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1635   -2.1171   -2.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3255   -3.2180   -2.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7588   -2.7587    1.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3549   -3.7067    0.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9  7  1  0
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  7  6  1  0
  6  4  1  0
  4  5  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
 13 28  1  0
 27 22  1  0
 16 28  1  0
 28 53  1  1
 31 54  1  0
 31 55  1  0
 31 56  1  0
 32 57  1  0
 32 58  1  0
 32 59  1  0
 12 42  1  6
 16 43  1  1
 17 44  1  0
 20 45  1  6
 21 46  1  0
 21 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
 26 51  1  0
 27 52  1  0
  7 38  1  1
  8 39  1  0
  8 40  1  0
  8 41  1  0
  2 36  1  0
  2 37  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
M  END

1602
  Mrv0541 02231215352D          

 33 35  0  0  1  0            999 V2000
    7.6202    2.5306    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215    0.8626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3231   -0.2020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6820    0.2396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4090    1.8553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0259   -1.5998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7288   -2.9975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0879   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8355    1.4506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215    2.8637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572    4.0328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6625    3.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2322    2.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2809   -2.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9838   -3.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4317   -4.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7336    2.9278    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  2 16  2  0  0  0  0
  3 19  1  0  0  0  0
  3 22  1  0  0  0  0
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 23 25  2  0  0  0  0
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 27 30  2  0  0  0  0
 28 30  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0267401

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1

> <INCHI_KEY>
PFOLLRNADZZWEX-FFGRCDKISA-N

> <FORMULA>
C21H27N3O7S

> <MOLECULAR_WEIGHT>
465.52

> <EXACT_MASS>
465.156970923

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
46.804522691634816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
1.471288066666666

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.348872411368657

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.72011839374805

> <JCHEM_PKA_STRONGEST_BASIC>
7.438310344205282

> <JCHEM_POLAR_SURFACE_AREA>
137.26

> <JCHEM_REFRACTIVITY>
113.76040000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bacampicillin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1602                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      14.224   4.724   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      10.120   1.610   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.670  -0.377   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      16.206   0.447   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.230   3.463   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      13.115  -2.986   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      12.560  -5.595   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      15.097  -4.771   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      12.760   2.708   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      10.120   5.346   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       7.947   7.528   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      12.760   4.248   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.129   3.478   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.224   2.232   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.207   4.254   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.207   2.701   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.375   4.383   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.375   2.573   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.700   0.767   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.632   4.950   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.545   6.041   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.146  -1.842   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.057   5.646   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.652  -2.162   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.655   4.159   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.970   6.737   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.167   3.763   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.482   6.341   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.591  -4.451   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.080   4.855   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.036  -7.060   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.006  -8.204   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0      12.569   5.465   0.000  0.00  0.00           H+0
CONECT    1   12   13                                                       
CONECT    2   16                                                            
CONECT    3   19   22                                                       
CONECT    4   19                                                            
CONECT    5   20                                                            
CONECT    6   22   29                                                       
CONECT    7   29   31                                                       
CONECT    8   29                                                            
CONECT    9   12   14   16                                                  
CONECT   10   15   20                                                       
CONECT   11   21                                                            
CONECT   12    1    9   15   33                                             
CONECT   13    1   14   17   18                                             
CONECT   14    9   13   19                                                  
CONECT   15   10   12   16                                                  
CONECT   16    2    9   15                                                  
CONECT   17   13                                                            
CONECT   18   13                                                            
CONECT   19    3    4   14                                                  
CONECT   20    5   10   21                                                  
CONECT   21   11   20   23                                                  
CONECT   22    3    6   24                                                  
CONECT   23   21   25   26                                                  
CONECT   24   22                                                            
CONECT   25   23   27                                                       
CONECT   26   23   28                                                       
CONECT   27   25   30                                                       
CONECT   28   26   30                                                       
CONECT   29    6    7    8                                                  
CONECT   30   27   28                                                       
CONECT   31    7   32                                                       
CONECT   32   31                                                            
CONECT   33   12                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
1'-Ethoxycarbonyloxyethyl-(6-D-alpha-aminophenylacetamido)penicillanate	ChEBI
1-[(Ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	ChEBI
Bacampicilina	ChEBI
Bacampicilline	ChEBI
Bacampicillinum	ChEBI
BAPC	Kegg
Penglobe	Kegg
1'-Ethoxycarbonyloxyethyl-(6-D-a-aminophenylacetamido)penicillanate	Generator
1'-Ethoxycarbonyloxyethyl-(6-D-a-aminophenylacetamido)penicillanic acid	Generator
1'-Ethoxycarbonyloxyethyl-(6-D-alpha-aminophenylacetamido)penicillanic acid	Generator
1'-Ethoxycarbonyloxyethyl-(6-D-α-aminophenylacetamido)penicillanate	Generator
1'-Ethoxycarbonyloxyethyl-(6-D-α-aminophenylacetamido)penicillanic acid	Generator
1-[(Ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	Generator
Bacampicillin hydrochloride	HMDB
Bacampicillin monohydrochloride	HMDB
Ethoxycarbonyloxyethyl ester OF ampicillin	HMDB
Bacampicine	HMDB
Carampicillin	HMDB

Chemical Formula

C₂₁H₂₇N₃O₇S

Average Mass

465.5200 Da

Monoisotopic Mass

465.15697 Da

IUPAC Name

1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Traditional Name

bacampicillin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1

InChI Key

PFOLLRNADZZWEX-FFGRCDKISA-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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Substituents

1,4-benzodiazepine
Alpha-amino acid or derivatives
Nitroaromatic compound
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Ketimine
Lactam
C-nitro compound
Organic nitro compound
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organic oxoazanium
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Imine
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic zwitterion
Organopnictogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

C-nitro compound (CHEBI:7581 )
1,4-benzodiazepinone (CHEBI:7581 )

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	1.17	ALOGPS
logP	1.47	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	11.72	ChemAxon
pKa (Strongest Basic)	7.44	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	137.26 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	113.76 m³·mol⁻¹	ChemAxon
Polarizability	46.8 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0015540

DrugBank ID

DB01602

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

390135

KEGG Compound ID

C08122

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bacampicillin

METLIN ID

Not Available

PubChem Compound

441397

PDB ID

Not Available

ChEBI ID

2968

Good Scents ID

Not Available

References

General References

Bodin NO, Ekstrom B, Forsgren U, Jalar LP, Magni L, Ramsay CH, Sjoberg B: Bacampicillin: a new orally well-absorbed derivative of ampicillin. Antimicrob Agents Chemother. 1975 Nov;8(5):518-25. doi: 10.1128/AAC.8.5.518. [PubMed:1211909 ]
Tan JS, Salstrom SJ: Bacampicillin, Ampicillin, Cephalothin, and Cephapirin levels in human blood and interstitial fluid. Antimicrob Agents Chemother. 1979 Apr;15(4):510-2. doi: 10.1128/AAC.15.4.510. [PubMed:464583 ]
Neu HC: The pharmacokinetics of bacampicillin. Rev Infect Dis. 1981 Jan-Feb;3(1):110-6. doi: 10.1093/clinids/3.1.110. [PubMed:7012993 ]
Craig WA, Gerber AU: Worldwide experience with bacampicillin administered twice a day. Rev Infect Dis. 1981 Jan-Feb;3(1):171-7. doi: 10.1093/clinids/3.1.171. [PubMed:7012998 ]
LOTUS database [Link]

Showing NP-Card for (2r)-2-amino-n-[(2s,5r,6r)-2-({1-[(ethoxycarbonyl)oxy]ethoxy}carbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylethanimidic acid (NP0267401)

MOL for NP0267401 ((2r)-2-amino-n-[(2s,5r,6r)-2-({1-[(ethoxycarbonyl)oxy]ethoxy}carbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylethanimidic acid)

3D MOL for NP0267401 ((2r)-2-amino-n-[(2s,5r,6r)-2-({1-[(ethoxycarbonyl)oxy]ethoxy}carbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylethanimidic acid)

3D SDF for NP0267401 ((2r)-2-amino-n-[(2s,5r,6r)-2-({1-[(ethoxycarbonyl)oxy]ethoxy}carbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylethanimidic acid)

3D-SDF for NP0267401 ((2r)-2-amino-n-[(2s,5r,6r)-2-({1-[(ethoxycarbonyl)oxy]ethoxy}carbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylethanimidic acid)

PDB for NP0267401 ((2r)-2-amino-n-[(2s,5r,6r)-2-({1-[(ethoxycarbonyl)oxy]ethoxy}carbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylethanimidic acid)

3D PDB for NP0267401 ((2r)-2-amino-n-[(2s,5r,6r)-2-({1-[(ethoxycarbonyl)oxy]ethoxy}carbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylethanimidic acid)

SMILES for NP0267401 ((2r)-2-amino-n-[(2s,5r,6r)-2-({1-[(ethoxycarbonyl)oxy]ethoxy}carbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylethanimidic acid)

INCHI for NP0267401 ((2r)-2-amino-n-[(2s,5r,6r)-2-({1-[(ethoxycarbonyl)oxy]ethoxy}carbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylethanimidic acid)

Structure for NP0267401 ((2r)-2-amino-n-[(2s,5r,6r)-2-({1-[(ethoxycarbonyl)oxy]ethoxy}carbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylethanimidic acid)

3D Structure for NP0267401 ((2r)-2-amino-n-[(2s,5r,6r)-2-({1-[(ethoxycarbonyl)oxy]ethoxy}carbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylethanimidic acid)