Ketcher 04141614102D 1   1.00000     0.00000     0

 24 26  0     1  0            999 V2000
   23.0878  -11.9199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0388  -10.6110    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.4927  -11.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6266  -11.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4927  -10.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0388  -12.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3260  -13.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3479  -13.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6787  -13.9232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0879  -10.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2217  -10.4200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3557  -10.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3557  -11.9199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4896  -10.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6233   -8.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6229   -7.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4888   -7.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3551   -7.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3553   -8.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4893   -9.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0879  -11.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3807  -12.6270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0878  -10.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0878   -9.9200    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 10  1  0     0  0
 10 21  1  0     0  0
 21  1  1  0     0  0
  1  6  1  0     0  0
 23  1  1  0     0  0
  2 23  1  0     0  0
  2  4  1  0     0  0
  6  4  1  0     0  0
  4  3  1  0     0  0
  4  5  1  0     0  0
  6  8  1  6     0  0
  8  7  1  0     0  0
  8  9  2  0     0  0
 10 11  1  1     0  0
 11 12  1  0     0  0
 12 14  1  0     0  0
 12 13  2  0     0  0
 14 20  1  0     0  0
 15 16  1  0     0  0
 15 20  2  0     0  0
 16 17  2  0     0  0
 17 18  1  0     0  0
 18 19  2  0     0  0
 19 20  1  0     0  0
 21 22  2  0     0  0
 23 24  1  6     0  0
M  END
> <ID>
CHEBI:18208

> <NAME>
benzylpenicillin

> <DEFINITION>
A penicillin in which the substituent at position 6 of the penam ring is a phenylacetamido group.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:25866; CHEBI:45073; CHEBI:7962; CHEBI:14743

> <SYNONYM>
PG; PENICILLIN G; Penicillin G; PCG; free penicillin II; benzylpenicillinic acid; Benzylpenicillin; benzyl benicillin; bensylpenicillin; 6-(2-phenylacetamido)penicillanic acid; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

> <IUPAC_NAME>
2,2-dimethyl-6beta-(phenylacetamido)penam-3alpha-carboxylic acid

> <INN>
benzylpenicillinum; benzylpenicilline; benzylpenicillin; bencilpenicilina

> <FORMULA>
C16H18N2O4S

> <MASS>
334.392

> <MONOISOTOPIC_MASS>
334.09873

> <CHARGE>
0

> <SMILES>
N12C([C@H]([C@]1(SC([C@@H]2C(O)=O)(C)C)[H])NC(CC3=CC=CC=C3)=O)=O

> <INCHI>
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

> <INCHIKEY>
JGSARLDLIJGVTE-MBNYWOFBSA-N

> <BEILSTEIN_REGISTRY_NUMBER>
44740

> <CAS_REGISTRY_NUMBER>
61-33-6

> <GMELIN_REGISTRY_NUMBER>
781913

> <REAXYS_REGISTRY_NUMBER>
44740

> <CHEMIDPLUS>
61-33-6

> <DRUGBANK_ACCESSION>
DB01053

> <KEGG_COMPOUND_ACCESSION>
C05551

> <KEGG_DRUG_ACCESSION>
D02336

> <LINCS_ACCESSION>
LSM-3229

> <PDBECHEM_ACCESSION>
PNN

> <WIKIPEDIA_ACCESSION>
Benzylpenicillin

> <PUBMED_CITATION>
10930630; 11431418; 11906332; 12569987; 12850488; 1384868; 16033609; 1709917; 2083978; 24485692; 24631718; 25998949; 27731424; 29017833; 29355985; 6161899; 7602118; 7716788

$$$$