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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:01 UTC

HMDB ID

HMDB0015540

Secondary Accession Numbers

HMDB15540

Metabolite Identification

Common Name

Bacampicillin

Description

Bacampicillin is a prodrug of ampicillin and is microbiologically inactive. It is absorbed following oral administration. During absorption from the gastrointestinal tract, bacampicillin is hydrolyzed by esterases present in the intestinal wall. It is microbiologically active as ampicillin, and exerts a bactericidal action through the inhibition of the biosynthesis of cell wall mucopeptides. It is used to cure infection of upper and lower respiratory tract; skin and soft tissue; urinary tract and acute uncomplicated gonococcal urethritis etc.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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
  5 20  2  0  0  0  0
  6 22  1  0  0  0  0
  6 29  1  0  0  0  0
  7 29  1  0  0  0  0
  7 31  1  0  0  0  0
  8 29  2  0  0  0  0
  9 12  1  0  0  0  0
  9 14  1  0  0  0  0
  9 16  1  0  0  0  0
 15 10  1  1  0  0  0
 10 20  1  0  0  0  0
 21 11  1  1  0  0  0
 12 15  1  0  0  0  0
 12 33  1  6  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 13 18  1  0  0  0  0
 14 19  1  6  0  0  0
 15 16  1  0  0  0  0
 20 21  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 23 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  2  0  0  0  0
 27 30  2  0  0  0  0
 28 30  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

HMDB0015540
     RDKit          3D
Bacampicillin
 59 61  0  0  0  0  0  0  0  0999 V2000
    6.6688    4.3975   -0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2510    3.6996    0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2723    2.8247    1.3006 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7128    1.7612    0.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0806    1.5251   -0.5196 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547    0.9267    1.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2240   -0.1569    0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6262   -1.4897    1.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8455   -0.1589    0.3253 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -0.0750   -0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7537    0.0287   -1.9182 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993   -0.1061   -0.8195 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1938   -0.4926    0.4665 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0017   -0.4262    1.8561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6063    0.1194    2.8180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2109   -1.2635    1.6761 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3756   -0.4525    1.4776 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5559   -0.7505    2.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5014   -1.7512    3.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8289   -0.0061    2.1020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7489   -0.5438    3.1203 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5356   -0.1886    0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9826   -0.7072   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7552   -0.8254   -1.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0565   -0.4219   -1.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6545    0.1038   -0.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8733    0.2147    0.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4586   -1.7863    0.5385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2353   -1.8601   -1.0996 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1766   -1.0253   -1.8797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1991   -2.1103   -2.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2479   -0.3326   -3.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5824    3.6700   -1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6482    4.7984   -0.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3645    5.1969   -0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1253    3.1100    0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5723    4.3812    1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7046   -0.1352   -0.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4160   -1.4890    2.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9248   -2.2416    0.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6310   -1.8141    0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2268    0.9240   -1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3356   -2.0519    2.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3884    0.3542    0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7479    1.0703    2.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1304   -0.7408    3.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0247   -1.5237    2.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9631   -1.0091   -0.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2798   -1.2419   -2.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6735   -0.5127   -2.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7024    0.4133   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3432    0.6274    1.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1857   -2.6291    0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8755   -1.8548   -3.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7064   -2.3176   -1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6251   -3.0154   -2.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2030   -0.7749   -3.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545    0.7341   -2.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4990   -0.5987   -3.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 16 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 30 12  1  0
 28 13  1  0
 27 22  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
  8 41  1  0
 12 42  1  6
 16 43  1  1
 17 44  1  0
 20 45  1  1
 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
 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
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
    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
  5 20  2  0  0  0  0
  6 22  1  0  0  0  0
  6 29  1  0  0  0  0
  7 29  1  0  0  0  0
  7 31  1  0  0  0  0
  8 29  2  0  0  0  0
  9 12  1  0  0  0  0
  9 14  1  0  0  0  0
  9 16  1  0  0  0  0
 15 10  1  1  0  0  0
 10 20  1  0  0  0  0
 21 11  1  1  0  0  0
 12 15  1  0  0  0  0
 12 33  1  6  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 13 18  1  0  0  0  0
 14 19  1  6  0  0  0
 15 16  1  0  0  0  0
 20 21  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 23 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  2  0  0  0  0
 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>
HMDB0015540

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0015540
     RDKit          3D
Bacampicillin
 59 61  0  0  0  0  0  0  0  0999 V2000
    6.6688    4.3975   -0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2510    3.6996    0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2723    2.8247    1.3006 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7128    1.7612    0.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0806    1.5251   -0.5196 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547    0.9267    1.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2240   -0.1569    0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6262   -1.4897    1.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8455   -0.1589    0.3253 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -0.0750   -0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7537    0.0287   -1.9182 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993   -0.1061   -0.8195 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1938   -0.4926    0.4665 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0017   -0.4262    1.8561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6063    0.1194    2.8180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2109   -1.2635    1.6761 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3756   -0.4525    1.4776 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5559   -0.7505    2.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5014   -1.7512    3.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8289   -0.0061    2.1020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7489   -0.5438    3.1203 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5356   -0.1886    0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9826   -0.7072   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7552   -0.8254   -1.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0565   -0.4219   -1.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6545    0.1038   -0.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8733    0.2147    0.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4586   -1.7863    0.5385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2353   -1.8601   -1.0996 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1766   -1.0253   -1.8797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1991   -2.1103   -2.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2479   -0.3326   -3.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5824    3.6700   -1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6482    4.7984   -0.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3645    5.1969   -0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1253    3.1100    0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5723    4.3812    1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7046   -0.1352   -0.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4160   -1.4890    2.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9248   -2.2416    0.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6310   -1.8141    0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2268    0.9240   -1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3356   -2.0519    2.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3884    0.3542    0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7479    1.0703    2.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1304   -0.7408    3.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0247   -1.5237    2.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9631   -1.0091   -0.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2798   -1.2419   -2.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6735   -0.5127   -2.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7024    0.4133   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3432    0.6274    1.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1857   -2.6291    0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8755   -1.8548   -3.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7064   -2.3176   -1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6251   -3.0154   -2.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2030   -0.7749   -3.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545    0.7341   -2.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4990   -0.5987   -3.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 16 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 30 12  1  0
 28 13  1  0
 27 22  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
  8 41  1  0
 12 42  1  6
 16 43  1  1
 17 44  1  0
 20 45  1  1
 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
 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
M  END

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

COMPND    HMDB0015540
HETATM    1  C1  UNL     1       6.669   4.398  -0.421  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.251   3.700   0.780  1.00  0.00           C  
HETATM    3  O1  UNL     1       6.272   2.825   1.301  1.00  0.00           O  
HETATM    4  C3  UNL     1       5.713   1.761   0.641  1.00  0.00           C  
HETATM    5  O2  UNL     1       6.081   1.525  -0.520  1.00  0.00           O  
HETATM    6  O3  UNL     1       4.755   0.927   1.201  1.00  0.00           O  
HETATM    7  C4  UNL     1       4.224  -0.157   0.474  1.00  0.00           C  
HETATM    8  C5  UNL     1       4.626  -1.490   1.098  1.00  0.00           C  
HETATM    9  O4  UNL     1       2.846  -0.159   0.325  1.00  0.00           O  
HETATM   10  C6  UNL     1       2.117  -0.075  -0.838  1.00  0.00           C  
HETATM   11  O5  UNL     1       2.754   0.029  -1.918  1.00  0.00           O  
HETATM   12  C7  UNL     1       0.599  -0.106  -0.820  1.00  0.00           C  
HETATM   13  N1  UNL     1       0.194  -0.493   0.466  1.00  0.00           N  
HETATM   14  C8  UNL     1      -0.002  -0.426   1.856  1.00  0.00           C  
HETATM   15  O6  UNL     1       0.606   0.119   2.818  1.00  0.00           O  
HETATM   16  C9  UNL     1      -1.211  -1.264   1.676  1.00  0.00           C  
HETATM   17  N2  UNL     1      -2.376  -0.453   1.478  1.00  0.00           N  
HETATM   18  C10 UNL     1      -3.556  -0.751   2.201  1.00  0.00           C  
HETATM   19  O7  UNL     1      -3.501  -1.751   3.006  1.00  0.00           O  
HETATM   20  C11 UNL     1      -4.829  -0.006   2.102  1.00  0.00           C  
HETATM   21  N3  UNL     1      -5.749  -0.544   3.120  1.00  0.00           N  
HETATM   22  C12 UNL     1      -5.536  -0.189   0.814  1.00  0.00           C  
HETATM   23  C13 UNL     1      -4.983  -0.707  -0.330  1.00  0.00           C  
HETATM   24  C14 UNL     1      -5.755  -0.825  -1.474  1.00  0.00           C  
HETATM   25  C15 UNL     1      -7.057  -0.422  -1.439  1.00  0.00           C  
HETATM   26  C16 UNL     1      -7.655   0.104  -0.314  1.00  0.00           C  
HETATM   27  C17 UNL     1      -6.873   0.215   0.814  1.00  0.00           C  
HETATM   28  C18 UNL     1      -0.459  -1.786   0.538  1.00  0.00           C  
HETATM   29  S1  UNL     1      -1.235  -1.860  -1.100  1.00  0.00           S  
HETATM   30  C19 UNL     1       0.177  -1.025  -1.880  1.00  0.00           C  
HETATM   31  C20 UNL     1       1.199  -2.110  -2.173  1.00  0.00           C  
HETATM   32  C21 UNL     1      -0.248  -0.333  -3.156  1.00  0.00           C  
HETATM   33  H1  UNL     1       6.582   3.670  -1.235  1.00  0.00           H  
HETATM   34  H2  UNL     1       5.648   4.798  -0.219  1.00  0.00           H  
HETATM   35  H3  UNL     1       7.364   5.197  -0.806  1.00  0.00           H  
HETATM   36  H4  UNL     1       8.125   3.110   0.399  1.00  0.00           H  
HETATM   37  H5  UNL     1       7.572   4.381   1.580  1.00  0.00           H  
HETATM   38  H6  UNL     1       4.705  -0.135  -0.524  1.00  0.00           H  
HETATM   39  H7  UNL     1       4.416  -1.489   2.204  1.00  0.00           H  
HETATM   40  H8  UNL     1       3.925  -2.242   0.687  1.00  0.00           H  
HETATM   41  H9  UNL     1       5.631  -1.814   0.836  1.00  0.00           H  
HETATM   42  H10 UNL     1       0.227   0.924  -1.129  1.00  0.00           H  
HETATM   43  H11 UNL     1      -1.336  -2.052   2.466  1.00  0.00           H  
HETATM   44  H12 UNL     1      -2.388   0.354   0.826  1.00  0.00           H  
HETATM   45  H13 UNL     1      -4.748   1.070   2.310  1.00  0.00           H  
HETATM   46  H14 UNL     1      -5.130  -0.741   3.967  1.00  0.00           H  
HETATM   47  H15 UNL     1      -6.025  -1.524   2.811  1.00  0.00           H  
HETATM   48  H16 UNL     1      -3.963  -1.009  -0.299  1.00  0.00           H  
HETATM   49  H17 UNL     1      -5.280  -1.242  -2.355  1.00  0.00           H  
HETATM   50  H18 UNL     1      -7.674  -0.513  -2.339  1.00  0.00           H  
HETATM   51  H19 UNL     1      -8.702   0.413  -0.331  1.00  0.00           H  
HETATM   52  H20 UNL     1      -7.343   0.627   1.706  1.00  0.00           H  
HETATM   53  H21 UNL     1       0.186  -2.629   0.784  1.00  0.00           H  
HETATM   54  H22 UNL     1       1.875  -1.855  -3.002  1.00  0.00           H  
HETATM   55  H23 UNL     1       1.706  -2.318  -1.216  1.00  0.00           H  
HETATM   56  H24 UNL     1       0.625  -3.015  -2.471  1.00  0.00           H  
HETATM   57  H25 UNL     1      -1.203  -0.775  -3.485  1.00  0.00           H  
HETATM   58  H26 UNL     1      -0.355   0.734  -2.965  1.00  0.00           H  
HETATM   59  H27 UNL     1       0.499  -0.599  -3.922  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3   36   37
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8    9   38
CONECT    8   39   40   41
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   30   42
CONECT   13   14   28
CONECT   14   15   15   16
CONECT   16   17   28   43
CONECT   17   18   44
CONECT   18   19   19   20
CONECT   20   21   22   45
CONECT   21   46   47
CONECT   22   23   23   27
CONECT   23   24   48
CONECT   24   25   25   49
CONECT   25   26   50
CONECT   26   27   27   51
CONECT   27   52
CONECT   28   29   53
CONECT   29   30
CONECT   30   31   32
CONECT   31   54   55   56
CONECT   32   57   58   59
END

HMDB0015540
     RDKit          3D
Bacampicillin
 59 61  0  0  0  0  0  0  0  0999 V2000
    6.6688    4.3975   -0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2510    3.6996    0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2723    2.8247    1.3006 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7128    1.7612    0.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0806    1.5251   -0.5196 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547    0.9267    1.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2240   -0.1569    0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6262   -1.4897    1.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8455   -0.1589    0.3253 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -0.0750   -0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7537    0.0287   -1.9182 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993   -0.1061   -0.8195 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1938   -0.4926    0.4665 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0017   -0.4262    1.8561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6063    0.1194    2.8180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2109   -1.2635    1.6761 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3756   -0.4525    1.4776 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5559   -0.7505    2.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5014   -1.7512    3.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8289   -0.0061    2.1020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7489   -0.5438    3.1203 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5356   -0.1886    0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9826   -0.7072   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7552   -0.8254   -1.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0565   -0.4219   -1.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6545    0.1038   -0.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8733    0.2147    0.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4586   -1.7863    0.5385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2353   -1.8601   -1.0996 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1766   -1.0253   -1.8797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1991   -2.1103   -2.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2479   -0.3326   -3.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5824    3.6700   -1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6482    4.7984   -0.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3645    5.1969   -0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1253    3.1100    0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5723    4.3812    1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7046   -0.1352   -0.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4160   -1.4890    2.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9248   -2.2416    0.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6310   -1.8141    0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2268    0.9240   -1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3356   -2.0519    2.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3884    0.3542    0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7479    1.0703    2.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1304   -0.7408    3.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0247   -1.5237    2.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9631   -1.0091   -0.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2798   -1.2419   -2.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6735   -0.5127   -2.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7024    0.4133   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3432    0.6274    1.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1857   -2.6291    0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8755   -1.8548   -3.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7064   -2.3176   -1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6251   -3.0154   -2.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2030   -0.7749   -3.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545    0.7341   -2.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4990   -0.5987   -3.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 16 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 30 12  1  0
 28 13  1  0
 27 22  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
  8 41  1  0
 12 42  1  6
 16 43  1  1
 17 44  1  0
 20 45  1  1
 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
 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
M  END

View in JSmol View Stereo Labels

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
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
BAPC	HMDB
Bacampicillin hydrochloride	HMDB
Bacampicillin monohydrochloride	HMDB
Ethoxycarbonyloxyethyl ester OF ampicillin	HMDB
Bacampicine	HMDB
Carampicillin	HMDB

Chemical Formula

C₂₁H₂₇N₃O₇S

Average Molecular Weight

465.52

Monoisotopic Molecular Weight

465.156970923

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

50972-17-3

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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillanic acid ester (CHEBI:2968 )

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

Cytoplasm (HMDB: HMDB0015540)

Source

Exogenous

Exogenous (HMDB: HMDB0015540)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.12 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	205.513	31661259
DarkChem	[M-H]-	200.419	31661259
DeepCCS	[M-2H]-	243.135	30932474
DeepCCS	[M+Na]+	217.815	30932474
AllCCS	[M+H]+	204.4	32859911
AllCCS	[M+H-H2O]+	202.6	32859911
AllCCS	[M+NH4]+	206.0	32859911
AllCCS	[M+Na]+	206.4	32859911
AllCCS	[M-H]-	201.4	32859911
AllCCS	[M+Na-2H]-	202.5	32859911
AllCCS	[M+HCOO]-	203.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bacampicillin	[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	4127.8	Standard polar	33892256
Bacampicillin	[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	2878.2	Standard non polar	33892256
Bacampicillin	[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	3252.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bacampicillin,1TMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C	3210.3	Semi standard non polar	33892256
Bacampicillin,1TMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C	2989.6	Standard non polar	33892256
Bacampicillin,1TMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C	4666.6	Standard polar	33892256
Bacampicillin,1TMS,isomer #2	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C	3118.8	Semi standard non polar	33892256
Bacampicillin,1TMS,isomer #2	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C	2952.5	Standard non polar	33892256
Bacampicillin,1TMS,isomer #2	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C	4893.0	Standard polar	33892256
Bacampicillin,2TMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C	3177.6	Semi standard non polar	33892256
Bacampicillin,2TMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C	3035.1	Standard non polar	33892256
Bacampicillin,2TMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)[C@H]2SC1(C)C	4185.4	Standard polar	33892256
Bacampicillin,2TMS,isomer #2	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C	3243.9	Semi standard non polar	33892256
Bacampicillin,2TMS,isomer #2	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C	3103.5	Standard non polar	33892256
Bacampicillin,2TMS,isomer #2	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C	4396.4	Standard polar	33892256
Bacampicillin,3TMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C	3266.0	Semi standard non polar	33892256
Bacampicillin,3TMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C	3150.9	Standard non polar	33892256
Bacampicillin,3TMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)[C@H]2SC1(C)C	3963.8	Standard polar	33892256
Bacampicillin,1TBDMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C	3385.4	Semi standard non polar	33892256
Bacampicillin,1TBDMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C	3187.7	Standard non polar	33892256
Bacampicillin,1TBDMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[C@H]2SC1(C)C	4675.3	Standard polar	33892256
Bacampicillin,1TBDMS,isomer #2	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C	3321.8	Semi standard non polar	33892256
Bacampicillin,1TBDMS,isomer #2	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C	3145.6	Standard non polar	33892256
Bacampicillin,1TBDMS,isomer #2	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C	4884.4	Standard polar	33892256
Bacampicillin,2TBDMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C	3510.8	Semi standard non polar	33892256
Bacampicillin,2TBDMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C	3424.6	Standard non polar	33892256
Bacampicillin,2TBDMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C	4323.9	Standard polar	33892256
Bacampicillin,2TBDMS,isomer #2	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C	3640.3	Semi standard non polar	33892256
Bacampicillin,2TBDMS,isomer #2	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C	3455.9	Standard non polar	33892256
Bacampicillin,2TBDMS,isomer #2	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C	4460.3	Standard polar	33892256
Bacampicillin,3TBDMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C	3792.2	Semi standard non polar	33892256
Bacampicillin,3TBDMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C	3692.5	Standard non polar	33892256
Bacampicillin,3TBDMS,isomer #1	CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]2SC1(C)C	4159.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bacampicillin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1900000000-210a80ea99d7d8b19c7c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bacampicillin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bacampicillin 10V, Positive-QTOF	splash10-052f-5914100000-b2bb79f625d3a39bd072	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bacampicillin 20V, Positive-QTOF	splash10-0a4l-7911000000-c5d3cfc8023d3a8d1c16	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bacampicillin 40V, Positive-QTOF	splash10-0a4i-6910000000-bb9f92cfef936fcb5cab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bacampicillin 10V, Negative-QTOF	splash10-0a4i-0391100000-56ef32146ff2caf816af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bacampicillin 20V, Negative-QTOF	splash10-0a4i-8593000000-92004702bfb034e6fad9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bacampicillin 40V, Negative-QTOF	splash10-056r-9510000000-079171b8e9ca83a521cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bacampicillin 10V, Positive-QTOF	splash10-0aos-0417900000-e6199826945c6f15ce9f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bacampicillin 20V, Positive-QTOF	splash10-0adi-2639600000-ef04d08a127b82678b0b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bacampicillin 40V, Positive-QTOF	splash10-0a4i-4910000000-ff0f3c2bb5b4f7c58350	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bacampicillin 10V, Negative-QTOF	splash10-0079-9015000000-d06a5bb09c37d08d5b91	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bacampicillin 20V, Negative-QTOF	splash10-03dj-9310000000-e4b469c81aee8f9b372c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bacampicillin 40V, Negative-QTOF	splash10-0006-9120000000-b9b13300295f6383c378	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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 DB01602	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01602	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01602

Phenol Explorer Compound ID

Not Available

FooDB 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

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

Not Available

Showing metabocard for Bacampicillin (HMDB0015540)

MOL for HMDB0015540 (Bacampicillin)

3D MOL for HMDB0015540 (Bacampicillin)

3D SDF for HMDB0015540 (Bacampicillin)

3D-SDF for HMDB0015540 (Bacampicillin)

PDB for HMDB0015540 (Bacampicillin)

3D PDB for HMDB0015540 (Bacampicillin)

SMILES for HMDB0015540 (Bacampicillin)

INCHI for HMDB0015540 (Bacampicillin)

Structure for HMDB0015540 (Bacampicillin)

3D Structure for HMDB0015540 (Bacampicillin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra