Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References transporters (10) Show 10 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015186

Secondary Accession Numbers

HMDB15186

Metabolite Identification

Common Name

Penicillin G

Description

Penicillin G is narrow spectrum antibiotic used to treat infections caused by susceptible bacteria. It is a natural penicillin antibiotic that is administered intravenously or intramuscularly due to poor oral absorption. Penicillin G may also be used in some cases as prophylaxis against susceptible organisms. Natural penicillins are considered the drugs of choice for several infections caused by susceptible gram positive aerobic organisms, such as Streptococcus pneumoniae, groups A, B, C and G streptococci, nonenterococcal group D streptococci, viridans group streptococci, and non-penicillinase producing staphylococcus. Aminoglycosides may be added for synergy against group B streptococcus (S. agalactiae), S. viridans, and Enterococcus faecalis. The natural penicillins may also be used as first or second line agents against susceptible gram positive aerobic bacilli such as Bacillus anthracis, Corynebacterium diphtheriae, and Erysipelothrix rhusiopathiae. Natural penicillins have limited activity against gram negative organisms; however, they may be used in some cases to treat infections caused by Neisseria meningitidis and Pasteurella. They are not generally used to treat anaerobic infections. Resistance patterns, susceptibility and treatment guidelines vary across regions.

Structure

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

HMDB0015186
     RDKit          3D
Penicillin G
 41 43  0  0  0  0  0  0  0  0999 V2000
   -4.2817    1.7291    1.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074    1.1814    0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5148    2.2348   -0.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8215    0.6311    1.8419 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6995   -1.1054    1.2180 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3494   -1.5459    0.8160 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7647   -0.6904    1.0784 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0616   -1.2610    1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744   -2.4615    0.8145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2594   -0.3945    1.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -0.0985    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7089    1.1839   -0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2683    1.5248   -1.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0121    0.6011   -2.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2163   -0.6878   -1.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426   -1.0146   -0.6477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8990   -1.4398   -0.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3937   -1.8328   -1.6801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0779   -0.7867   -0.1719 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3171   -0.0595   -0.1612 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4186   -0.9261    0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6182   -0.6022    0.4096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1721   -2.3079    0.3993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2155    1.6425    0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3324    1.3802    2.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0867    2.8405    1.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8761    3.2244    0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9402    2.0405   -1.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4242    2.1366   -0.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3442   -1.7962    1.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1695   -2.6344    0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6433    0.3090    1.2714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9738   -1.0043    1.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9890    0.5357    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1245    1.8833    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.5060   -2.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4620    0.8351   -3.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8010   -1.3875   -2.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7971   -2.0076   -0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116    0.3041   -1.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4765   -2.6793    1.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20  2  1  0
 19  5  1  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  1
  6 31  1  1
  7 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 20 40  1  6
 23 41  1  0
M  END

1053
  Mrv0541 02231215122D          

 24 26  0  0  1  0            999 V2000
    7.6201    1.0703    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215   -0.5975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3230   -1.6623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6819   -1.2207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4089    0.3950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8354   -0.0096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215    1.4034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8354    0.8154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1049    0.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6201   -0.2646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0036    0.8188    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0036   -0.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7724   -0.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7724    0.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8750   -1.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6241    1.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0420    1.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    1.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0295    0.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625    2.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2322    0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7335    1.4675    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1  9  1  0  0  0  0
  2 12  2  0  0  0  0
  3 15  1  0  0  0  0
  4 15  2  0  0  0  0
  5 16  2  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  1  0  0  0  0
 11  7  1  1  0  0  0
  7 16  1  0  0  0  0
  8 11  1  0  0  0  0
  8 24  1  6  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  6  0  0  0
 11 12  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  2  0  0  0  0
 21 23  2  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015186

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1

> <INCHI_KEY>
JGSARLDLIJGVTE-MBNYWOFBSA-N

> <FORMULA>
C16H18N2O4S

> <MOLECULAR_WEIGHT>
334.39

> <EXACT_MASS>
334.098727764

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.541594084546915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
1.0806779529999997

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.119397282151533

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5292810836901047

> <JCHEM_PKA_STRONGEST_BASIC>
-2.634074595453018

> <JCHEM_POLAR_SURFACE_AREA>
86.71

> <JCHEM_REFRACTIVITY>
84.52780000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
penicillin G

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015186
     RDKit          3D
Penicillin G
 41 43  0  0  0  0  0  0  0  0999 V2000
   -4.2817    1.7291    1.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074    1.1814    0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5148    2.2348   -0.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8215    0.6311    1.8419 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6995   -1.1054    1.2180 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3494   -1.5459    0.8160 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7647   -0.6904    1.0784 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0616   -1.2610    1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744   -2.4615    0.8145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2594   -0.3945    1.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -0.0985    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7089    1.1839   -0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2683    1.5248   -1.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0121    0.6011   -2.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2163   -0.6878   -1.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426   -1.0146   -0.6477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8990   -1.4398   -0.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3937   -1.8328   -1.6801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0779   -0.7867   -0.1719 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3171   -0.0595   -0.1612 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4186   -0.9261    0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6182   -0.6022    0.4096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1721   -2.3079    0.3993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2155    1.6425    0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3324    1.3802    2.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0867    2.8405    1.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8761    3.2244    0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9402    2.0405   -1.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4242    2.1366   -0.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3442   -1.7962    1.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1695   -2.6344    0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6433    0.3090    1.2714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9738   -1.0043    1.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9890    0.5357    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1245    1.8833    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.5060   -2.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4620    0.8351   -3.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8010   -1.3875   -2.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7971   -2.0076   -0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116    0.3041   -1.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4765   -2.6793    1.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20  2  1  0
 19  5  1  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  1
  6 31  1  1
  7 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 20 40  1  6
 23 41  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1053                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      14.224   1.998   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      10.120  -1.115   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.670  -3.103   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      16.206  -2.279   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.230   0.737   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      12.759  -0.018   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      10.120   2.620   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      12.759   1.522   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.129   0.752   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.224  -0.494   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.207   1.528   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.207  -0.024   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.375  -0.153   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.375   1.657   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.700  -1.958   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.632   2.224   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.545   3.315   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.057   2.920   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.655   1.433   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.970   4.011   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.167   1.037   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.482   3.615   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080   2.129   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      12.569   2.739   0.000  0.00  0.00           H+0
CONECT    1    8    9                                                       
CONECT    2   12                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5   16                                                            
CONECT    6    8   10   12                                                  
CONECT    7   11   16                                                       
CONECT    8    1    6   11   24                                             
CONECT    9    1   10   13   14                                             
CONECT   10    6    9   15                                                  
CONECT   11    7    8   12                                                  
CONECT   12    2    6   11                                                  
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15    3    4   10                                                  
CONECT   16    5    7   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   23                                                       
CONECT   23   21   22                                                       
CONECT   24    8                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0015186
HETATM    1  C1  UNL     1      -4.282   1.729   1.359  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.107   1.181   0.642  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.515   2.235  -0.282  1.00  0.00           C  
HETATM    4  S1  UNL     1      -1.822   0.631   1.842  1.00  0.00           S  
HETATM    5  C4  UNL     1      -1.699  -1.105   1.218  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.349  -1.546   0.816  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.765  -0.690   1.078  1.00  0.00           N  
HETATM    8  C6  UNL     1       2.062  -1.261   1.063  1.00  0.00           C  
HETATM    9  O1  UNL     1       2.274  -2.461   0.814  1.00  0.00           O  
HETATM   10  C7  UNL     1       3.259  -0.395   1.355  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.903  -0.099   0.050  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.709   1.184  -0.458  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.268   1.525  -1.675  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.012   0.601  -2.379  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.216  -0.688  -1.881  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.643  -1.015  -0.648  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.899  -1.440  -0.587  1.00  0.00           C  
HETATM   18  O2  UNL     1      -0.394  -1.833  -1.680  1.00  0.00           O  
HETATM   19  N2  UNL     1      -2.078  -0.787  -0.172  1.00  0.00           N  
HETATM   20  C15 UNL     1      -3.317  -0.059  -0.161  1.00  0.00           C  
HETATM   21  C16 UNL     1      -4.419  -0.926   0.216  1.00  0.00           C  
HETATM   22  O3  UNL     1      -5.618  -0.602   0.410  1.00  0.00           O  
HETATM   23  O4  UNL     1      -4.172  -2.308   0.399  1.00  0.00           O  
HETATM   24  H1  UNL     1      -5.215   1.642   0.810  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.332   1.380   2.430  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.087   2.840   1.485  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.876   3.224   0.058  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.940   2.040  -1.304  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.424   2.137  -0.237  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.344  -1.796   1.748  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.169  -2.634   0.981  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.643   0.309   1.271  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.974  -1.004   1.966  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.989   0.536   1.844  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.124   1.883   0.117  1.00  0.00           H  
HETATM   36  H13 UNL     1       4.146   2.506  -2.106  1.00  0.00           H  
HETATM   37  H14 UNL     1       5.462   0.835  -3.335  1.00  0.00           H  
HETATM   38  H15 UNL     1       5.801  -1.387  -2.457  1.00  0.00           H  
HETATM   39  H16 UNL     1       4.797  -2.008  -0.273  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.512   0.304  -1.217  1.00  0.00           H  
HETATM   41  H18 UNL     1      -4.477  -2.679   1.285  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4   20
CONECT    3   27   28   29
CONECT    4    5
CONECT    5    6   19   30
CONECT    6    7   17   31
CONECT    7    8   32
CONECT    8    9    9   10
CONECT   10   11   33   34
CONECT   11   12   12   16
CONECT   12   13   35
CONECT   13   14   14   36
CONECT   14   15   37
CONECT   15   16   16   38
CONECT   16   39
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   21   40
CONECT   21   22   22   23
CONECT   23   41
END

HMDB0015186
     RDKit          3D
Penicillin G
 41 43  0  0  0  0  0  0  0  0999 V2000
   -4.2817    1.7291    1.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074    1.1814    0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5148    2.2348   -0.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8215    0.6311    1.8419 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6995   -1.1054    1.2180 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3494   -1.5459    0.8160 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7647   -0.6904    1.0784 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0616   -1.2610    1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744   -2.4615    0.8145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2594   -0.3945    1.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -0.0985    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7089    1.1839   -0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2683    1.5248   -1.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0121    0.6011   -2.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2163   -0.6878   -1.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426   -1.0146   -0.6477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8990   -1.4398   -0.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3937   -1.8328   -1.6801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0779   -0.7867   -0.1719 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3171   -0.0595   -0.1612 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4186   -0.9261    0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6182   -0.6022    0.4096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1721   -2.3079    0.3993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2155    1.6425    0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3324    1.3802    2.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0867    2.8405    1.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8761    3.2244    0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9402    2.0405   -1.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4242    2.1366   -0.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3442   -1.7962    1.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1695   -2.6344    0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6433    0.3090    1.2714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9738   -1.0043    1.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9890    0.5357    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1245    1.8833    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.5060   -2.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4620    0.8351   -3.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8010   -1.3875   -2.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7971   -2.0076   -0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116    0.3041   -1.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4765   -2.6793    1.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20  2  1  0
 19  5  1  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  1
  6 31  1  1
  7 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 20 40  1  6
 23 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
6-(2-Phenylacetamido)penicillanic acid	ChEBI
Bencilpenicilina	ChEBI
Bensylpenicillin	ChEBI
Benzyl benicillin	ChEBI
Benzylpenicilline	ChEBI
Benzylpenicillinic acid	ChEBI
Benzylpenicillinum	ChEBI
Free penicillin II	ChEBI
PCG	ChEBI
PG	ChEBI
Benzylpenicillin	Kegg
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
6-(2-Phenylacetamido)penicillanate	Generator
Benzylpenicillinate	Generator
Antibioticos brand OF penicillin g sodium	HMDB
Britannia brand OF penicillin g sodium	HMDB
Or-pen	HMDB
Pekamin	HMDB
Penibiot	HMDB
Pfizerpen	HMDB
Sodipen	HMDB
Van-pen-g	HMDB
Benzylpenicillin potassium	HMDB
CEPA brand OF penicillin g sodium	HMDB
Grünenthal brand OF penicillin g potassium	HMDB
Jenapharm brand OF penicillin g sodium	HMDB
Llorente brand OF penicillin g sodium	HMDB
Medical brand OF penicillin g sodium	HMDB
Normon brand OF penicillin g sodium	HMDB
Penicillin grünenthal	HMDB
Sodium penicillin	HMDB
Ursopen	HMDB
Benpen	HMDB
Coliriocilina	HMDB
Ern brand OF penicillin g sodium	HMDB
Lakeside brand OF penicillin g sodium	HMDB
Medical brand OF penicillin g potassium	HMDB
Ortega brand OF penicillin g potassium	HMDB
Penicilina g llorente	HMDB
Penicillin g potassium	HMDB
Penilevel	HMDB
Peniroger	HMDB
Pfizer brand OF penicillin g potassium	HMDB
Sodiopen	HMDB
Sodium benzylpenicillin	HMDB
UCB brand OF penicillin g sodium	HMDB
Unicilina	HMDB
Bioniche brand OF penicillin g sodium	HMDB
CSL Brand OF penicillin g sodium	HMDB
Clonmel brand OF penicillin g sodium	HMDB
Crystapen	HMDB
Parcillin	HMDB
Parmed brand OF penicillin g potassium	HMDB
Pengesod	HMDB
Penicillin g jenapharm	HMDB
Penicillin g sodium	HMDB
Vangard brand OF penicillin g potassium	HMDB
Penicillin g	ChEBI

Chemical Formula

C₁₆H₁₈N₂O₄S

Average Molecular Weight

334.39

Monoisotopic Molecular Weight

334.098727764

IUPAC Name

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

Traditional Name

penicillin G

CAS Registry Number

61-33-6

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1

InChI Key

JGSARLDLIJGVTE-MBNYWOFBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Penicillin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Phenylacetamide
Penam
Monocyclic benzene moiety
Benzenoid
Beta-lactam
Thiazolidine
Tertiary carboxylic acid amide
Azetidine
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Dialkylthioether
Hemithioaminal
Thioether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:18208 )
penams (C05551 )

Ontology

Not Available

Placenta (HMDB: HMDB0015186)

Biofluid or Excreta

Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015186)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	214 - 217 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.28 g/L	Not Available
LogP	1.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	174.546	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001284

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.28 g/L	ALOGPS
logP	1.92	ALOGPS
logP	1.08	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.71 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	84.53 m³·mol⁻¹	ChemAxon
Polarizability	33.54 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	175.949	31661259
DarkChem	[M-H]-	167.976	31661259
DeepCCS	[M-2H]-	211.189	30932474
DeepCCS	[M+Na]+	186.249	30932474
AllCCS	[M+H]+	174.8	32859911
AllCCS	[M+H-H2O]+	172.0	32859911
AllCCS	[M+NH4]+	177.4	32859911
AllCCS	[M+Na]+	178.1	32859911
AllCCS	[M-H]-	177.5	32859911
AllCCS	[M+Na-2H]-	177.4	32859911
AllCCS	[M+HCOO]-	177.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Penicillin G	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1)C(O)=O	4237.5	Standard polar	33892256
Penicillin G	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1)C(O)=O	2594.4	Standard non polar	33892256
Penicillin G	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1)C(O)=O	2770.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Penicillin G,1TMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)CC3=CC=CC=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2628.8	Semi standard non polar	33892256
Penicillin G,1TMS,isomer #2	CC1(C)S[C@@H]2[C@H](N(C(=O)CC3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	2595.8	Semi standard non polar	33892256
Penicillin G,2TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)CC3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2555.9	Semi standard non polar	33892256
Penicillin G,2TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)CC3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2612.2	Standard non polar	33892256
Penicillin G,2TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)CC3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3163.9	Standard polar	33892256
Penicillin G,1TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)CC3=CC=CC=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2870.9	Semi standard non polar	33892256
Penicillin G,1TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](N(C(=O)CC3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	2813.0	Semi standard non polar	33892256
Penicillin G,2TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)CC3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2995.3	Semi standard non polar	33892256
Penicillin G,2TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)CC3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3052.5	Standard non polar	33892256
Penicillin G,2TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)CC3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3361.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Penicillin G GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9111000000-c26265c0b3a7beb3ec2b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Penicillin G GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9010000000-bdb726ea699de6cfed1c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Penicillin G GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Penicillin G 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penicillin G 30V, Negative-QTOF	splash10-00di-9000000000-ea40b52a677fe59a6de1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penicillin G 40V, Negative-QTOF	splash10-00di-9000000000-6b0ced613495ec7786cd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penicillin G 30V, Positive-QTOF	splash10-0006-9200000000-fa9a998d05d785d35da3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penicillin G 0V, Positive-QTOF	splash10-03fr-0905000000-c9ebf3278702ed3da9ae	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penicillin G 10V, Positive-QTOF	splash10-03fr-1900000000-cd0eb273a5bf00dd85b5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penicillin G 0V, Positive-QTOF	splash10-03fr-0905000000-45176c1f74d7cbe0cfa4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penicillin G 10V, Positive-QTOF	splash10-03fr-1901000000-1ba3d8bff84b3c6fb96a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penicillin G 30V, Positive-QTOF	splash10-01ox-9500000000-f670b692d530e470875a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penicillin G 20V, Negative-QTOF	splash10-00di-9300000000-fdbd4edd10aa9a29a4f3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Penicillin G 10V, Negative-QTOF	splash10-0006-2900000000-e8940b6589f2b95e3403	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicillin G 10V, Positive-QTOF	splash10-0400-2932000000-92082dd94f7c14c5ee1d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicillin G 20V, Positive-QTOF	splash10-0900-4920000000-957ebfd788454d96fea6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicillin G 40V, Positive-QTOF	splash10-0btc-9400000000-b7dc0535d63c2db40535	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicillin G 10V, Negative-QTOF	splash10-0006-0920000000-d47e30dbb9656c5046b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicillin G 20V, Negative-QTOF	splash10-0006-0930000000-1e3178016f1241e6e74e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicillin G 40V, Negative-QTOF	splash10-002f-9600000000-c161010ceaa25b82e55e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicillin G 10V, Positive-QTOF	splash10-000i-0229000000-8e49abf86f7c84100d01	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicillin G 20V, Positive-QTOF	splash10-0hfx-3952000000-dd2b2b12cee1c489c1c2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicillin G 40V, Positive-QTOF	splash10-0006-8900000000-56c739c89af830c4b25b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicillin G 10V, Negative-QTOF	splash10-001i-0019000000-847ef8ad73cfc8da19b4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicillin G 20V, Negative-QTOF	splash10-0a4l-9702000000-9fa2f54365ec6ff4b041	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicillin G 40V, Negative-QTOF	splash10-0006-9100000000-5dea18185be80fe32e19	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Placenta

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 DB01053	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01053	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01053

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5693

KEGG Compound ID

C05551

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzylpenicillin

METLIN ID

Not Available

PubChem Compound

5904

PDB ID

PNN

ChEBI ID

18208

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

Eagle H, Newman E, Musselman AD, Robinson M, Birmingham M: THE RENAL CLEARANCE OF PENICILLINS F, G, K, AND X IN RABBITS AND MAN. J Clin Invest. 1947 Sep;26(5):903-18. [PubMed:16695494 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

References

Tamai I, Nezu J, Uchino H, Sai Y, Oku A, Shimane M, Tsuji A: Molecular identification and characterization of novel members of the human organic anion transporter (OATP) family. Biochem Biophys Res Commun. 2000 Jun 24;273(1):251-60. [PubMed:10873595 ]

Enzyme Details

2. Solute carrier family 22 member 5

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:: SLC22A5
Uniprot ID:: O76082
Molecular weight:: 62751.1

References

Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865 ]

Enzyme Details

3. Solute carrier organic anion transporter family member 2B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost
Gene Name:: SLCO2B1
Uniprot ID:: O94956
Molecular weight:: 76697.9

References

Tamai I, Nezu J, Uchino H, Sai Y, Oku A, Shimane M, Tsuji A: Molecular identification and characterization of novel members of the human organic anion transporter (OATP) family. Biochem Biophys Res Commun. 2000 Jun 24;273(1):251-60. [PubMed:10873595 ]

Enzyme Details

4. Solute carrier family 22 member 11

General function:: Involved in transporter activity
Specific function:: Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:: SLC22A11
Uniprot ID:: Q9NSA0
Molecular weight:: 59970.9

References

Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, Endou H: Role of human organic anion transporter 4 in the transport of ochratoxin A. Biochim Biophys Acta. 2002 Jun 12;1590(1-3):64-75. [PubMed:12063169 ]
Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]

Enzyme Details

5. Solute carrier family 22 member 4

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET)
Gene Name:: SLC22A4
Uniprot ID:: Q9H015
Molecular weight:: 62154.5

References

Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [PubMed:10215651 ]

Enzyme Details

6. Solute carrier family 15 member 1

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

References

Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]
Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [PubMed:15618677 ]

Enzyme Details

7. Solute carrier family 15 member 2

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

References

Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]

Enzyme Details

8. Solute carrier organic anion transporter family member 4A1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate
Gene Name:: SLCO4A1
Uniprot ID:: Q96BD0
Molecular weight:: 77192.5

References

Tamai I, Nezu J, Uchino H, Sai Y, Oku A, Shimane M, Tsuji A: Molecular identification and characterization of novel members of the human organic anion transporter (OATP) family. Biochem Biophys Res Commun. 2000 Jun 24;273(1):251-60. [PubMed:10873595 ]

Enzyme Details

9. Solute carrier organic anion transporter family member 3A1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as estrone-3-sulfate (PubMed:10873595). Mediates transport of prostaglandins (PG) E1 and E2, thyroxine (T4), deltorphin II, BQ-123 and vasopressin, but not DPDPE (a derivative of enkephalin lacking an N-terminal tyrosine residue), estrone-3- sulfate, taurocholate, digoxin nor DHEAS (PubMed:16971491)
Gene Name:: SLCO3A1
Uniprot ID:: Q9UIG8
Molecular weight:: 76552.1

References

Tamai I, Nezu J, Uchino H, Sai Y, Oku A, Shimane M, Tsuji A: Molecular identification and characterization of novel members of the human organic anion transporter (OATP) family. Biochem Biophys Res Commun. 2000 Jun 24;273(1):251-60. [PubMed:10873595 ]

Enzyme Details

10. Solute carrier family 22 member 6

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

References

Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [PubMed:11669456 ]
Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]
Hosoyamada M, Sekine T, Kanai Y, Endou H: Molecular cloning and functional expression of a multispecific organic anion transporter from human kidney. Am J Physiol. 1999 Jan;276(1 Pt 2):F122-8. [PubMed:9887087 ]
Lu R, Chan BS, Schuster VL: Cloning of the human kidney PAH transporter: narrow substrate specificity and regulation by protein kinase C. Am J Physiol. 1999 Feb;276(2 Pt 2):F295-303. [PubMed:9950961 ]
Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577 ]
Hasegawa M, Kusuhara H, Sugiyama D, Ito K, Ueda S, Endou H, Sugiyama Y: Functional involvement of rat organic anion transporter 3 (rOat3; Slc22a8) in the renal uptake of organic anions. J Pharmacol Exp Ther. 2002 Mar;300(3):746-53. [PubMed:11861777 ]

Showing metabocard for Penicillin G (HMDB0015186)

MOL for HMDB0015186 (Penicillin G)

3D MOL for HMDB0015186 (Penicillin G)

3D SDF for HMDB0015186 (Penicillin G)

3D-SDF for HMDB0015186 (Penicillin G)

PDB for HMDB0015186 (Penicillin G)

3D PDB for HMDB0015186 (Penicillin G)

SMILES for HMDB0015186 (Penicillin G)

INCHI for HMDB0015186 (Penicillin G)

Structure for HMDB0015186 (Penicillin G)

3D Structure for HMDB0015186 (Penicillin G)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Transporters

References

References

References

References

References

References

References

References

References

References