Milk Composition Database: Showing metabocard for Penicillin G (BMDB0063636)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

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Record Information

Version

1.0

Creation Date

2018-12-04 20:29:04 UTC

Update Date

2020-06-04 20:42:28 UTC

MCDB ID

BMDB0063636

Secondary Accession Numbers

BMDB63636

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 SDF PDB SMILES InChI

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 )

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
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	1	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

Concentrations

Status	Value		Reference	Details
Detected and Quantified	0.036 uM		Nina Bilandžić, B...	details

External Links

HMDB ID

HMDB0015186

DrugBank ID

DB01053

Phenol Explorer Compound ID

Not Available

FoodDB 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

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Nina Bilandžić, Božica Solomun Kolanović, Ivana Varenina, Giampiero Scortichini, Loredana Annunziata, Matko Brstilo, Nevenka Rudan (2011). Nina Bilandžić, Božica Solomun Kolanović, Ivana Varenina, Giampiero Scortichini, Loredana Annunziata, Matko Brstilo, Nevenka Rudan. Veterinary drug residues determination in raw milk in Croatia. Food Control. Volume 22, Issue 12, December 2011, Pages 1941-1948. Food Control.

Showing metabocard for Penicillin G (BMDB0063636)

Structure for BMDB0063636 (Penicillin G)