Penicillin G

C₁₆H₁₈N₂O₄SCAS 61-33-6334.39 g/mol

Open in Covalent MOL file

Amide Carboxylic acid Lactam Sulfide

Properties

Molecular formula: C₁₆H₁₈N₂O₄S
Molar mass: 334.39 g/mol
Exact mass: 334.0987 Da
Melting point: 82–83 °C
pKa: 2.72
logP: 1.70Crippen estimate
Polar surface area: 90.2 Å²
H-bond donors / acceptors: 2 / 4
Rotatable bonds: 4
Stereocentres: R, R, Sin SMILES atom order

Hazards

Danger

H317 May cause an allergic skin reaction100% of notifiers
H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled48% of notifiers
H400 Very toxic to aquatic life46.7% of notifiers
H412 Harmful to aquatic life with long lasting effects46.7% of notifiers

Aggregated from 75 ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Precautionary statements

P233, P260, P261, P271, P272, P273, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P391, P403, P501

Identifiers

CAS number

61-33-6

SMILES

CC1(C)S[C@@H]2[C@H](N=C(O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)O

InChIKey

JGSARLDLIJGVTE-MBNYWOFBSA-N

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

Weigh it out

Type any one amount. The others follow from the molar mass.

Names and synonyms

32 names · show all

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]- (2S,5R,6R)-
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- [2S-(2α,5α,6β)]-
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Benzyl-6-aminopenicillinic acid
Benzylpenicillin
Liquacillin
Phenylacetamidopenicillanic acid
Benzylpenicillin G
Cilopen
Penicillinic acid, (phenylmethyl)-
Penicillin, (phenylmethyl)-
Specilline G
Benzylpenicillinic acid
Gelacillin
Pradupen
Dropcillin
Pharmacillin
Cilloral
Penicillin
(5R,6R)-Benzylpenicillin
Ursopen
Phenylacetyl-6-aminopenicillanic acid
Free penicillin G
Free penicillin II
Free benzylpenicillin
NSC 193396
Crysticillin 300 AS
(2S,5R,6R)-3,3-Dimethyl-6-(2-(phenylacetylamino)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Allpen
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptan-2-carboxylic acid

Work with Penicillin G

Predict the NMR spectrum1H and 13C shifts with multiplicities Make a solutionWhat to weigh for any molarity and volume Check drug-likenessLipinski, Veber and lead-likeness Isotope patternExact mass and the mass spectrum pattern

Stereoisomers, salts and isotopologues

The same compound in another form: other stereochemistry, a salt or hydrate, the free acid or base, or an isotope-labelled version.

Benzathine penicillin1538-09-6Salt Penicillin G procaine54-35-3Salt Penicillin G potassium113-98-4Salt Penicillin G sodium69-57-8Salt Benzylpenicillin procaine monohydrate6130-64-9Salt

Similar compounds

Carbenicillin4697-36-366 % similar Ampicillin69-53-464 % similar Ampicillin trihydrate7177-48-261 % similar Azlocillin37091-66-056 % similar Amoxicillin26787-78-055 % similar Ticarcillin34787-01-455 % similar Amoxicillin trihydrate61336-70-753 % similar Piperacillin61477-96-152 % similar

Tanimoto similarity of circular fingerprints over the whole catalogue.

All similar compounds

Same formula

Phenazine ethosulfate10510-77-7

Elsewhere

PubChem CAS Common Chemistry NIST WebBook