MiMeDB: Showing metabocard for Beta GalNAc globoside (homo sapiens) (MMDBc0049447)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:33:47 UTC

Update Date

2022-09-01 02:16:26 UTC

MiMeDB ID

MMDBc0049447

Metabolite Identification

Common Name

Beta GalNAc globoside (homo sapiens)

Description

Penicillin G, also known as benzylpenicilline or PCG, 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. Penicillin G is a drug which is used for use in the treatment of severe infections caused by penicillin g-susceptible microorganisms when rapid and high penicillin levels are required such as in the treatment of septicemia, meningitis, pericarditis, endocarditis and severe pneumonia. A penicillin in which the substituent at position 6 of the penam ring is a phenylacetamido group. Penicillin G is an extremely weak basic (essentially neutral) compound (based on its pKa).

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>
MMDBc0049447

> <DATABASE_NAME>
MIME

> <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

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

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

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

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

#<MetaboliteProteinLink:0x000055b76c5b2448>

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Fungi	Ascomycota	2	Human Feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB		details
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597	details

External Links

HMDB ID

HMDB0015186

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

References

Synthesis Reference

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. doi: 10.1172/JCI101885. [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 ]

Showing metabocard for Beta GalNAc globoside (homo sapiens) (MMDBc0049447)

MOL for #<Metabolite:0x000055b7691c96e0>

3D MOL for #<Metabolite:0x000055b7691c96e0>

3D SDF for #<Metabolite:0x000055b7691c96e0>

3D-SDF for #<Metabolite:0x000055b7691c96e0>

PDB for #<Metabolite:0x000055b7691c96e0>

3D PDB for #<Metabolite:0x000055b7691c96e0>

SMILES for #<Metabolite:0x000055b7691c96e0>

INCHI for #<Metabolite:0x000055b7691c96e0>

Structure for #<Metabolite:0x000055b7691c96e0>

3D Structure for #<Metabolite:0x000055b7691c96e0>