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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

HMDB0015542

Secondary Accession Numbers

HMDB15542

Metabolite Identification

Common Name

Pivampicillin

Description

Pivampicillin, also known as pondocillin or berocillin, belongs to the class of organic compounds known as phenyl-1,2,4-triazoles. These are organic compounds containing a 1,2,4-triazole substituted by a phenyl group. Based on a literature review a significant number of articles have been published on Pivampicillin.

Structure

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

1604
  Mrv0541 02231215352D          

 33 35  0  0  1  0            999 V2000
    7.6202    2.1383    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215    0.4703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3231   -0.5943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6820   -0.1528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4090    1.4630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0259   -1.9921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0879   -2.9482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8355    1.0583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215    2.4713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572    3.6404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8355    1.8833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1050    1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6202    0.8034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0037    1.8868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0037    1.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7725    1.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7725    0.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8751    0.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6242    2.2594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0420    2.8440    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5780   -1.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2447    2.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7288   -3.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0295    1.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625    3.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2809   -2.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1768   -4.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3420   -3.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1158   -2.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2322    1.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8652    3.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7336    2.5354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  2 15  2  0  0  0  0
  3 18  1  0  0  0  0
  3 21  1  0  0  0  0
  4 18  2  0  0  0  0
  5 19  2  0  0  0  0
  6 21  1  0  0  0  0
  6 26  1  0  0  0  0
  7 26  2  0  0  0  0
  8 11  1  0  0  0  0
  8 13  1  0  0  0  0
  8 15  1  0  0  0  0
 14  9  1  1  0  0  0
  9 19  1  0  0  0  0
 20 10  1  1  0  0  0
 11 14  1  0  0  0  0
 11 33  1  6  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  6  0  0  0
 14 15  1  0  0  0  0
 19 20  1  0  0  0  0
 20 22  1  0  0  0  0
 22 24  2  0  0  0  0
 22 25  1  0  0  0  0
 23 26  1  0  0  0  0
 23 27  1  0  0  0  0
 23 28  1  0  0  0  0
 23 29  1  0  0  0  0
 24 30  1  0  0  0  0
 25 31  2  0  0  0  0
 30 32  2  0  0  0  0
 31 32  1  0  0  0  0
M  END

HMDB0015542
     RDKit          3D
Pivampicillin
 61 63  0  0  0  0  0  0  0  0999 V2000
    5.9728    2.2499    1.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3574    1.5143    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8391    1.2625    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9748    2.3888   -0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6301    0.2295    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2613   -0.8412    0.3295 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2583    0.2274    0.1584 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5878   -1.0235    0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1950   -0.8195    0.0638 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2314   -1.8036    0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6024   -2.9948    0.2068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2156   -1.4001   -0.0724 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2316   -0.0263   -0.4066 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0119    1.0846   -1.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7973    1.5796   -2.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3054    1.6653   -0.6537 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4119    1.2050   -1.2882 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5067    0.7523   -1.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1548    1.3302   -2.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1491   -0.5786   -1.5589 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9645   -1.0657   -2.6599 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1049   -0.2667   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0208   -1.2242   -0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9158   -0.9467    0.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8917    0.2737    1.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9850    1.2379    1.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0733    0.9417    0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8028    0.8796    0.5453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0401   -0.1657    1.3260 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0455   -1.6986    1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3031   -1.9180    2.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214   -2.8301    0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0030    2.7615    1.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8988    1.4710    2.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7728    2.9591    1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0281    0.2738    0.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1390    1.1380   -0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3817    2.0969    0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9940    2.1252   -1.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8912    3.4492   -0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7687    2.3565   -1.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8935   -1.5457   -0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8636   -1.6607    1.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5917   -2.0707   -0.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1022    2.7818   -0.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3918    2.2988   -2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4026   -1.3217   -1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0146   -2.1089   -2.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6719   -0.6561   -3.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0773   -2.2118   -0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6395   -1.7192    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6024    0.5039    2.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9848    2.1845    1.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3605    1.7210   -0.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1027    1.4037    1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0493   -0.9701    2.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9869   -2.4703    3.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5734   -2.5911    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1346   -3.0224   -0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0443   -2.6044    1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6263   -3.7910    1.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  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
  3 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  0
  8 43  1  0
 12 44  1  6
 16 45  1  1
 17 46  1  0
 20 47  1  1
 21 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
 26 53  1  0
 27 54  1  0
 28 55  1  1
 31 56  1  0
 31 57  1  0
 31 58  1  0
 32 59  1  0
 32 60  1  0
 32 61  1  0
M  END

1604
  Mrv0541 02231215352D          

 33 35  0  0  1  0            999 V2000
    7.6202    2.1383    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215    0.4703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3231   -0.5943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6820   -0.1528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4090    1.4630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0259   -1.9921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0879   -2.9482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8355    1.0583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215    2.4713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572    3.6404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8355    1.8833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1050    1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6202    0.8034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0037    1.8868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0037    1.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7725    1.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7725    0.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8751    0.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6242    2.2594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0420    2.8440    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5780   -1.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2447    2.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7288   -3.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0295    1.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625    3.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2809   -2.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1768   -4.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3420   -3.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1158   -2.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2322    1.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8652    3.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7336    2.5354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  2 15  2  0  0  0  0
  3 18  1  0  0  0  0
  3 21  1  0  0  0  0
  4 18  2  0  0  0  0
  5 19  2  0  0  0  0
  6 21  1  0  0  0  0
  6 26  1  0  0  0  0
  7 26  2  0  0  0  0
  8 11  1  0  0  0  0
  8 13  1  0  0  0  0
  8 15  1  0  0  0  0
 14  9  1  1  0  0  0
  9 19  1  0  0  0  0
 20 10  1  1  0  0  0
 11 14  1  0  0  0  0
 11 33  1  6  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  6  0  0  0
 14 15  1  0  0  0  0
 19 20  1  0  0  0  0
 20 22  1  0  0  0  0
 22 24  2  0  0  0  0
 22 25  1  0  0  0  0
 23 26  1  0  0  0  0
 23 27  1  0  0  0  0
 23 28  1  0  0  0  0
 23 29  1  0  0  0  0
 24 30  1  0  0  0  0
 25 31  2  0  0  0  0
 30 32  2  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015542

> <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)OCOC(=O)C(C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H29N3O6S/c1-21(2,3)20(29)31-11-30-19(28)15-22(4,5)32-18-14(17(27)25(15)18)24-16(26)13(23)12-9-7-6-8-10-12/h6-10,13-15,18H,11,23H2,1-5H3,(H,24,26)/t13-,14-,15+,18-/m1/s1

> <INCHI_KEY>
ZEMIJUDPLILVNQ-ZXFNITATSA-N

> <FORMULA>
C22H29N3O6S

> <MOLECULAR_WEIGHT>
463.547

> <EXACT_MASS>
463.177706365

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
47.53968324049653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
2.065192519666666

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.348867428920723

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.707929021475366

> <JCHEM_PKA_STRONGEST_BASIC>
7.438306945693415

> <JCHEM_POLAR_SURFACE_AREA>
128.03

> <JCHEM_REFRACTIVITY>
116.24830000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pivampicillin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015542
     RDKit          3D
Pivampicillin
 61 63  0  0  0  0  0  0  0  0999 V2000
    5.9728    2.2499    1.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3574    1.5143    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8391    1.2625    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9748    2.3888   -0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6301    0.2295    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2613   -0.8412    0.3295 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2583    0.2274    0.1584 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5878   -1.0235    0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1950   -0.8195    0.0638 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2314   -1.8036    0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6024   -2.9948    0.2068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2156   -1.4001   -0.0724 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2316   -0.0263   -0.4066 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0119    1.0846   -1.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7973    1.5796   -2.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3054    1.6653   -0.6537 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4119    1.2050   -1.2882 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5067    0.7523   -1.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1548    1.3302   -2.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1491   -0.5786   -1.5589 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9645   -1.0657   -2.6599 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1049   -0.2667   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0208   -1.2242   -0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9158   -0.9467    0.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8917    0.2737    1.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9850    1.2379    1.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0733    0.9417    0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8028    0.8796    0.5453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0401   -0.1657    1.3260 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0455   -1.6986    1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3031   -1.9180    2.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214   -2.8301    0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0030    2.7615    1.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8988    1.4710    2.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7728    2.9591    1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0281    0.2738    0.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1390    1.1380   -0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3817    2.0969    0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9940    2.1252   -1.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8912    3.4492   -0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7687    2.3565   -1.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8935   -1.5457   -0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8636   -1.6607    1.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5917   -2.0707   -0.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1022    2.7818   -0.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3918    2.2988   -2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4026   -1.3217   -1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0146   -2.1089   -2.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6719   -0.6561   -3.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0773   -2.2118   -0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6395   -1.7192    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6024    0.5039    2.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9848    2.1845    1.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3605    1.7210   -0.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1027    1.4037    1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0493   -0.9701    2.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9869   -2.4703    3.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5734   -2.5911    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1346   -3.0224   -0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0443   -2.6044    1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6263   -3.7910    1.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  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
  3 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  0
  8 43  1  0
 12 44  1  6
 16 45  1  1
 17 46  1  0
 20 47  1  1
 21 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
 26 53  1  0
 27 54  1  0
 28 55  1  1
 31 56  1  0
 31 57  1  0
 31 58  1  0
 32 59  1  0
 32 60  1  0
 32 61  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1604                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      14.224   3.991   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      10.120   0.878   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.670  -1.109   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      16.206  -0.285   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.230   2.731   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      13.115  -3.719   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      15.097  -5.503   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      12.760   1.975   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      10.120   4.613   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       7.947   6.795   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      12.760   3.515   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.129   2.745   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.224   1.500   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.207   3.522   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.207   1.969   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.375   3.651   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.375   1.840   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.700   0.035   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.632   4.218   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.545   5.309   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.146  -2.574   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.057   4.913   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.560  -6.328   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.655   3.426   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.970   6.005   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.591  -5.183   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.530  -7.472   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.705  -7.358   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.416  -5.297   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.167   3.031   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.482   5.609   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.080   4.122   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0      12.569   4.733   0.000  0.00  0.00           H+0
CONECT    1   11   12                                                       
CONECT    2   15                                                            
CONECT    3   18   21                                                       
CONECT    4   18                                                            
CONECT    5   19                                                            
CONECT    6   21   26                                                       
CONECT    7   26                                                            
CONECT    8   11   13   15                                                  
CONECT    9   14   19                                                       
CONECT   10   20                                                            
CONECT   11    1    8   14   33                                             
CONECT   12    1   13   16   17                                             
CONECT   13    8   12   18                                                  
CONECT   14    9   11   15                                                  
CONECT   15    2    8   14                                                  
CONECT   16   12                                                            
CONECT   17   12                                                            
CONECT   18    3    4   13                                                  
CONECT   19    5    9   20                                                  
CONECT   20   10   19   22                                                  
CONECT   21    3    6                                                       
CONECT   22   20   24   25                                                  
CONECT   23   26   27   28   29                                             
CONECT   24   22   30                                                       
CONECT   25   22   31                                                       
CONECT   26    6    7   23                                                  
CONECT   27   23                                                            
CONECT   28   23                                                            
CONECT   29   23                                                            
CONECT   30   24   32                                                       
CONECT   31   25   32                                                       
CONECT   32   30   31                                                       
CONECT   33   11                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

COMPND    HMDB0015542
HETATM    1  C1  UNL     1       5.973   2.250   1.509  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.357   1.514   0.237  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.839   1.263   0.207  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.975   2.389  -0.963  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.630   0.229   0.244  1.00  0.00           C  
HETATM    6  O1  UNL     1       6.261  -0.841   0.329  1.00  0.00           O  
HETATM    7  O2  UNL     1       4.258   0.227   0.158  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.588  -1.023   0.181  1.00  0.00           C  
HETATM    9  O3  UNL     1       2.195  -0.820   0.064  1.00  0.00           O  
HETATM   10  C7  UNL     1       1.231  -1.804   0.075  1.00  0.00           C  
HETATM   11  O4  UNL     1       1.602  -2.995   0.207  1.00  0.00           O  
HETATM   12  C8  UNL     1      -0.216  -1.400  -0.072  1.00  0.00           C  
HETATM   13  N1  UNL     1      -0.232  -0.026  -0.407  1.00  0.00           N  
HETATM   14  C9  UNL     1       0.012   1.085  -1.217  1.00  0.00           C  
HETATM   15  O5  UNL     1       0.797   1.580  -2.039  1.00  0.00           O  
HETATM   16  C10 UNL     1      -1.305   1.665  -0.654  1.00  0.00           C  
HETATM   17  N2  UNL     1      -2.412   1.205  -1.288  1.00  0.00           N  
HETATM   18  C11 UNL     1      -3.507   0.752  -1.918  1.00  0.00           C  
HETATM   19  O6  UNL     1      -4.155   1.330  -2.868  1.00  0.00           O  
HETATM   20  C12 UNL     1      -4.149  -0.579  -1.559  1.00  0.00           C  
HETATM   21  N3  UNL     1      -4.964  -1.066  -2.660  1.00  0.00           N  
HETATM   22  C13 UNL     1      -5.105  -0.267  -0.449  1.00  0.00           C  
HETATM   23  C14 UNL     1      -6.021  -1.224  -0.102  1.00  0.00           C  
HETATM   24  C15 UNL     1      -6.916  -0.947   0.894  1.00  0.00           C  
HETATM   25  C16 UNL     1      -6.892   0.274   1.534  1.00  0.00           C  
HETATM   26  C17 UNL     1      -5.985   1.238   1.200  1.00  0.00           C  
HETATM   27  C18 UNL     1      -5.073   0.942   0.177  1.00  0.00           C  
HETATM   28  C19 UNL     1      -0.803   0.880   0.545  1.00  0.00           C  
HETATM   29  S1  UNL     1      -2.040  -0.166   1.326  1.00  0.00           S  
HETATM   30  C20 UNL     1      -1.046  -1.699   1.100  1.00  0.00           C  
HETATM   31  C21 UNL     1      -0.303  -1.918   2.380  1.00  0.00           C  
HETATM   32  C22 UNL     1      -2.021  -2.830   0.905  1.00  0.00           C  
HETATM   33  H1  UNL     1       5.003   2.762   1.405  1.00  0.00           H  
HETATM   34  H2  UNL     1       5.899   1.471   2.312  1.00  0.00           H  
HETATM   35  H3  UNL     1       6.773   2.959   1.778  1.00  0.00           H  
HETATM   36  H4  UNL     1       8.028   0.274   0.686  1.00  0.00           H  
HETATM   37  H5  UNL     1       8.139   1.138  -0.871  1.00  0.00           H  
HETATM   38  H6  UNL     1       8.382   2.097   0.675  1.00  0.00           H  
HETATM   39  H7  UNL     1       4.994   2.125  -1.373  1.00  0.00           H  
HETATM   40  H8  UNL     1       5.891   3.449  -0.586  1.00  0.00           H  
HETATM   41  H9  UNL     1       6.769   2.356  -1.742  1.00  0.00           H  
HETATM   42  H10 UNL     1       3.894  -1.546  -0.775  1.00  0.00           H  
HETATM   43  H11 UNL     1       3.864  -1.661   1.020  1.00  0.00           H  
HETATM   44  H12 UNL     1      -0.592  -2.071  -0.906  1.00  0.00           H  
HETATM   45  H13 UNL     1      -1.102   2.782  -0.528  1.00  0.00           H  
HETATM   46  H14 UNL     1      -2.392   2.299  -2.107  1.00  0.00           H  
HETATM   47  H15 UNL     1      -3.403  -1.322  -1.317  1.00  0.00           H  
HETATM   48  H16 UNL     1      -5.015  -2.109  -2.671  1.00  0.00           H  
HETATM   49  H17 UNL     1      -4.672  -0.656  -3.572  1.00  0.00           H  
HETATM   50  H18 UNL     1      -6.077  -2.212  -0.585  1.00  0.00           H  
HETATM   51  H19 UNL     1      -7.639  -1.719   1.152  1.00  0.00           H  
HETATM   52  H20 UNL     1      -7.602   0.504   2.332  1.00  0.00           H  
HETATM   53  H21 UNL     1      -5.985   2.184   1.715  1.00  0.00           H  
HETATM   54  H22 UNL     1      -4.360   1.721  -0.073  1.00  0.00           H  
HETATM   55  H23 UNL     1      -0.103   1.404   1.210  1.00  0.00           H  
HETATM   56  H24 UNL     1      -0.049  -0.970   2.916  1.00  0.00           H  
HETATM   57  H25 UNL     1      -0.987  -2.470   3.079  1.00  0.00           H  
HETATM   58  H26 UNL     1       0.573  -2.591   2.261  1.00  0.00           H  
HETATM   59  H27 UNL     1      -2.135  -3.022  -0.201  1.00  0.00           H  
HETATM   60  H28 UNL     1      -3.044  -2.604   1.257  1.00  0.00           H  
HETATM   61  H29 UNL     1      -1.626  -3.791   1.338  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3    4    5
CONECT    3   36   37   38
CONECT    4   39   40   41
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   42   43
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   30   44
CONECT   13   14   28
CONECT   14   15   15   16
CONECT   16   17   28   45
CONECT   17   18   46
CONECT   18   19   19   20
CONECT   20   21   22   47
CONECT   21   48   49
CONECT   22   23   23   27
CONECT   23   24   50
CONECT   24   25   25   51
CONECT   25   26   52
CONECT   26   27   27   53
CONECT   27   54
CONECT   28   29   55
CONECT   29   30
CONECT   30   31   32
CONECT   31   56   57   58
CONECT   32   59   60   61
END

HMDB0015542
     RDKit          3D
Pivampicillin
 61 63  0  0  0  0  0  0  0  0999 V2000
    5.9728    2.2499    1.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3574    1.5143    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8391    1.2625    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9748    2.3888   -0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6301    0.2295    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2613   -0.8412    0.3295 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2583    0.2274    0.1584 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5878   -1.0235    0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1950   -0.8195    0.0638 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2314   -1.8036    0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6024   -2.9948    0.2068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2156   -1.4001   -0.0724 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2316   -0.0263   -0.4066 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0119    1.0846   -1.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7973    1.5796   -2.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3054    1.6653   -0.6537 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4119    1.2050   -1.2882 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5067    0.7523   -1.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1548    1.3302   -2.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1491   -0.5786   -1.5589 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9645   -1.0657   -2.6599 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1049   -0.2667   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0208   -1.2242   -0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9158   -0.9467    0.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8917    0.2737    1.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9850    1.2379    1.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0733    0.9417    0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8028    0.8796    0.5453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0401   -0.1657    1.3260 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0455   -1.6986    1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3031   -1.9180    2.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214   -2.8301    0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0030    2.7615    1.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8988    1.4710    2.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7728    2.9591    1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0281    0.2738    0.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1390    1.1380   -0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3817    2.0969    0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9940    2.1252   -1.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8912    3.4492   -0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7687    2.3565   -1.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8935   -1.5457   -0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8636   -1.6607    1.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5917   -2.0707   -0.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1022    2.7818   -0.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3918    2.2988   -2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4026   -1.3217   -1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0146   -2.1089   -2.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6719   -0.6561   -3.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0773   -2.2118   -0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6395   -1.7192    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6024    0.5039    2.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9848    2.1845    1.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3605    1.7210   -0.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1027    1.4037    1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0493   -0.9701    2.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9869   -2.4703    3.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5734   -2.5911    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1346   -3.0224   -0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0443   -2.6044    1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6263   -3.7910    1.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  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
  3 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  0
  8 43  1  0
 12 44  1  6
 16 45  1  1
 17 46  1  0
 20 47  1  1
 21 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
 26 53  1  0
 27 54  1  0
 28 55  1  1
 31 56  1  0
 31 57  1  0
 31 58  1  0
 32 59  1  0
 32 60  1  0
 32 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ampicillin pivaloyloxymethyl ester	ChEBI
Pivaloyloxymethyl ampicillinate	ChEBI
Pivampicilina	ChEBI
Pivampicilline	ChEBI
Pivampicillinum	ChEBI
Pondocillin	Kegg
Pivaloyloxymethyl ampicillinic acid	Generator
Pivaloylampicillin	HMDB
Berocillin	HMDB
Serra pamies brand OF pivampicillin hydrochloride	HMDB
Pivampicillin hydrochloride	HMDB
Ampicillin pivaloyl ester	HMDB
Ester, ampicillin pivaloyl	HMDB
Hydrochloride, pivampicillin	HMDB
Leo brand OF pivampicillin	HMDB
Monohydrochloride, pivampicillin	HMDB
Pivamiser	HMDB
Pivampicillin monohydrochloride	HMDB

Chemical Formula

C₂₂H₂₉N₃O₆S

Average Molecular Weight

463.547

Monoisotopic Molecular Weight

463.177706365

IUPAC Name

[(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate

Traditional Name

pivampicillin

CAS Registry Number

33817-20-8

SMILES

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

InChI Identifier

InChI=1S/C22H29N3O6S/c1-21(2,3)20(29)31-11-30-19(28)15-22(4,5)32-18-14(17(27)25(15)18)24-16(26)13(23)12-9-7-6-8-10-12/h6-10,13-15,18H,11,23H2,1-5H3,(H,24,26)/t13-,14-,15+,18-/m1/s1

InChI Key

ZEMIJUDPLILVNQ-ZXFNITATSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenyl-1,2,4-triazoles. These are organic compounds containing a 1,2,4-triazole substituted by a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Triazoles

Direct Parent

Phenyl-1,2,4-triazoles

Alternative Parents

Substituents

Phenyl-1,2,4-triazole
Benzoic acid or derivatives
Benzoic acid
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:49005 )
phenols (CHEBI:49005 )
benzoic acids (CHEBI:49005 )
triazoles (CHEBI:49005 )

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: HMDB0015542)

Source

Exogenous

Exogenous (HMDB: HMDB0015542)

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	0.035 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.035 g/L	ALOGPS
logP	1.43	ALOGPS
logP	2.07	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	7.44	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.03 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	116.25 m³·mol⁻¹	ChemAxon
Polarizability	47.54 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]+	204.908	31661259
DarkChem	[M-H]-	196.685	31661259
DeepCCS	[M-2H]-	249.107	30932474
DeepCCS	[M+Na]+	223.539	30932474
AllCCS	[M+H]+	203.7	32859911
AllCCS	[M+H-H2O]+	202.1	32859911
AllCCS	[M+NH4]+	205.3	32859911
AllCCS	[M+Na]+	205.7	32859911
AllCCS	[M-H]-	203.8	32859911
AllCCS	[M+Na-2H]-	205.0	32859911
AllCCS	[M+HCOO]-	206.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pivampicillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OCOC(=O)C(C)(C)C	3855.8	Standard polar	33892256
Pivampicillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OCOC(=O)C(C)(C)C	2819.3	Standard non polar	33892256
Pivampicillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OCOC(=O)C(C)(C)C	3269.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pivampicillin,1TMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	3148.3	Semi standard non polar	33892256
Pivampicillin,1TMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	3024.6	Standard non polar	33892256
Pivampicillin,1TMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	4483.4	Standard polar	33892256
Pivampicillin,1TMS,isomer #2	CC(C)(C)C(=O)OCOC(=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	3070.1	Semi standard non polar	33892256
Pivampicillin,1TMS,isomer #2	CC(C)(C)C(=O)OCOC(=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	3002.8	Standard non polar	33892256
Pivampicillin,1TMS,isomer #2	CC(C)(C)C(=O)OCOC(=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	4659.9	Standard polar	33892256
Pivampicillin,2TMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	3128.5	Semi standard non polar	33892256
Pivampicillin,2TMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	3094.6	Standard non polar	33892256
Pivampicillin,2TMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	4020.6	Standard polar	33892256
Pivampicillin,2TMS,isomer #2	CC(C)(C)C(=O)OCOC(=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	3172.8	Semi standard non polar	33892256
Pivampicillin,2TMS,isomer #2	CC(C)(C)C(=O)OCOC(=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	3156.8	Standard non polar	33892256
Pivampicillin,2TMS,isomer #2	CC(C)(C)C(=O)OCOC(=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	4223.9	Standard polar	33892256
Pivampicillin,3TMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	3206.2	Semi standard non polar	33892256
Pivampicillin,3TMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	3230.3	Standard non polar	33892256
Pivampicillin,3TMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	3813.4	Standard polar	33892256
Pivampicillin,1TBDMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	3341.8	Semi standard non polar	33892256
Pivampicillin,1TBDMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	3234.0	Standard non polar	33892256
Pivampicillin,1TBDMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	4501.0	Standard polar	33892256
Pivampicillin,1TBDMS,isomer #2	CC(C)(C)C(=O)OCOC(=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	3290.8	Semi standard non polar	33892256
Pivampicillin,1TBDMS,isomer #2	CC(C)(C)C(=O)OCOC(=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	3203.8	Standard non polar	33892256
Pivampicillin,1TBDMS,isomer #2	CC(C)(C)C(=O)OCOC(=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	4663.9	Standard polar	33892256
Pivampicillin,2TBDMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	3465.3	Semi standard non polar	33892256
Pivampicillin,2TBDMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	3487.0	Standard non polar	33892256
Pivampicillin,2TBDMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	4162.3	Standard polar	33892256
Pivampicillin,2TBDMS,isomer #2	CC(C)(C)C(=O)OCOC(=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	3599.4	Semi standard non polar	33892256
Pivampicillin,2TBDMS,isomer #2	CC(C)(C)C(=O)OCOC(=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	3517.8	Standard non polar	33892256
Pivampicillin,2TBDMS,isomer #2	CC(C)(C)C(=O)OCOC(=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	4292.2	Standard polar	33892256
Pivampicillin,3TBDMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	3764.6	Semi standard non polar	33892256
Pivampicillin,3TBDMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	3780.2	Standard non polar	33892256
Pivampicillin,3TBDMS,isomer #1	CC(C)(C)C(=O)OCOC(=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	4005.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pivampicillin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4900000000-459356a4997f59da0598	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pivampicillin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pivampicillin 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 - Pivampicillin 10V, Positive-QTOF	splash10-0pi0-1922100000-c66d44e9e103153e78e7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivampicillin 20V, Positive-QTOF	splash10-0a4i-4921000000-e513d7e709a4cc359313	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivampicillin 40V, Positive-QTOF	splash10-0a4i-9800000000-1d45b7913c48a4570128	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivampicillin 10V, Negative-QTOF	splash10-0a4i-0290100000-8fa5f97dea1c97508c9f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivampicillin 20V, Negative-QTOF	splash10-0a4i-1691100000-3c1b28211f3589a2e3b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivampicillin 40V, Negative-QTOF	splash10-0ke9-9630000000-8cb9ef389fad4dc01d14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivampicillin 10V, Positive-QTOF	splash10-01ot-0322900000-3504b69e69554572682b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivampicillin 20V, Positive-QTOF	splash10-0a4i-7954200000-eb67af5b14cd5f26d30b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivampicillin 40V, Positive-QTOF	splash10-0a4i-5901000000-f16b60a416509c0adb29	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivampicillin 10V, Negative-QTOF	splash10-01t9-1329700000-2f3c07f08b5464f78950	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivampicillin 20V, Negative-QTOF	splash10-0udl-4934000000-ae133ff906d357093abb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivampicillin 40V, Negative-QTOF	splash10-0006-9220000000-a556e0bfb78074f98c8d	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 DB01604	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01604	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01604

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30899

KEGG Compound ID

C11750

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pivampicillin

METLIN ID

Not Available

PubChem Compound

33478

PDB ID

Not Available

ChEBI ID

8255

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

Chanteux H, Van Bambeke F, Mingeot-Leclercq MP, Tulkens PM: Accumulation and oriented transport of ampicillin in Caco-2 cells from its pivaloyloxymethylester prodrug, pivampicillin. Antimicrob Agents Chemother. 2005 Apr;49(4):1279-88. [PubMed:15793098 ]
Albertson TE, Louie S, Chan AL: The diagnosis and treatment of elderly patients with acute exacerbation of chronic obstructive pulmonary disease and chronic bronchitis. J Am Geriatr Soc. 2010 Mar;58(3):570-9. doi: 10.1111/j.1532-5415.2010.02741.x. [PubMed:20398122 ]

Showing metabocard for Pivampicillin (HMDB0015542)

MOL for HMDB0015542 (Pivampicillin)

3D MOL for HMDB0015542 (Pivampicillin)

3D SDF for HMDB0015542 (Pivampicillin)

3D-SDF for HMDB0015542 (Pivampicillin)

PDB for HMDB0015542 (Pivampicillin)

3D PDB for HMDB0015542 (Pivampicillin)

SMILES for HMDB0015542 (Pivampicillin)

INCHI for HMDB0015542 (Pivampicillin)

Structure for HMDB0015542 (Pivampicillin)

3D Structure for HMDB0015542 (Pivampicillin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra