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113-98-4 molecular structure
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potassium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

ChemBase ID: 102196
Molecular Formular: C16H17KN2O4S
Molecular Mass: 372.48048
Monoisotopic Mass: 372.05460971
SMILES and InChIs

SMILES:
[K+].O=C([O-])[C@@H]1N2C(=O)[C@@H](NC(=O)Cc3ccccc3)[C@H]2SC1(C)C
Canonical SMILES:
O=C(Cc1ccccc1)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C.[K+]
InChI:
InChI=1S/C16H18N2O4S.K/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);/q;+1/p-1/t11-,12+,14-;/m1./s1
InChIKey:
IYNDLOXRXUOGIU-LQDWTQKMSA-M

Cite this record

CBID:102196 http://www.chembase.cn/molecule-102196.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
potassium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
IUPAC Traditional name
potassium benzylpenicillin(1-)
Synonyms
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Potassium Salt
Penicillin G Potassium Salt
Benzylpenicillin Potassium
Cosmopen
Cristapen
Crytapen
Eskacillin
Falapen
Forpen
Hipercilina
Hyasorb
Hylenta
M-Cillin
Monopen
NSC 131815
Notaral
Pentid
Pentids
Potassium 6-(Phenylacetamido)penicillanate
Potassium Benzylpenicillin
Potassium Benzylpenicillinate
Potassium Penicillin G
Scotcil
Tabilin
Benzyl Penicillinate Potassium Salt
Benzylpenicillin potassium salt
PENICILLIN G POTASSIUM SALT
Benzylpenicillin
Penicillin G potassium salt
苄青霉素 钾盐
青霉素 G 钾盐
CAS Number
113-98-4
EC Number
204-038-0
MDL Number
MFCD00036193
Beilstein Number
3832841
PubChem SID
24870324
24898970
24899067
24898878
162088610
PubChem CID
23664709
E Number
E705

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.5292811  H Acceptors
H Donor LogD (pH = 5.5) -0.8828292 
LogD (pH = 7.4) -2.2857618  Log P 1.080678 
Molar Refractivity 95.3649 cm3 Polarizability 33.23371 Å3
Polar Surface Area 89.54 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
H2O: soluble100 mg/mL expand Show data source
Water expand Show data source
Apperance
Off-White Solid expand Show data source
powder expand Show data source
Melting Point
214-217 expand Show data source
246-248°C (dec.) expand Show data source
Optical Rotation
[α]20/D +290±5°, c = 2% in H2O expand Show data source
Absorption Wavelength
λ: 264 nm Amax: ≤0.850 expand Show data source
λ: 280 nm Amax: ≤0.100 expand Show data source
Storage Condition
2-8°C expand Show data source
Hygroscopic, -20°C Freezer, Under Inert Atmosphere expand Show data source
RTECS
XH9700000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Risk Statements
42/43 expand Show data source
Safety Statements
36/37 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H317 expand Show data source
GHS Precautionary statements
P280 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98.0% (HPLC) expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Potency
1440-1680 units per mg expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Suitability
meets USP testing specifications expand Show data source
suitable for 1694 per US EPA expand Show data source
suitable for cell culture expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
λ
0.2 % in H2O expand Show data source
Empirical Formula (Hill Notation)
C16H17KN2O4S expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02194536 external link
Cell Culture Reagent
Potassium salt
Approx. 1,500-1,700 units/mg
MP Biomedicals - 02100543 external link
Potassium Salt
Activity: ~1,500-1,700 units/mg
Sigma Aldrich - P7794 external link
Application
Recommended for use in cell culture applications at 100,000 units/L. Solutions should be filter sterilized and stored at 2-8 °C for up to 1 week, -20 °C for extended periods. Solutions are stable at 37 °C for 3 days.
Biochem/physiol Actions
Mode of Action: Inhibits bacterial cell wall synthesis.Antimicrobial spectrum: Gram-positive bacteria
Mode of Action: Use to inhibit the synthesis of bacterial cell walls by inhibition of the cell wall peptidoglycan chain cross-lining. Antimicrobial spectrum: Gram-positive bacteria
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - PENK external link
Biochem/physiol Actions
Mode of Action: Inhibits bacterial cell wall synthesis.Antimicrobial spectrum: Gram-positive bacteria
Penicillin G is active against gram-positive and gram-negative aerobic and anaerobic bacteria. Penicillin G inhibits cell wall synthesis by binding to penicillin binding proteins (PBPs) which inhibits peptidoglycan chain cross-lining. Penicillin G is stable against hydrolysis by β-lactamases, such as penicillinases and cephalosporinases.
Application
Penicillin G is a narrow spectrum antibiotic. It is the drug of choice for Streptococcus pneumoniae, groups A, B, C and G streptococci, nonenterococcal group D streptococci, viridans group streptococci, and non-penicillinase producing staphylococcus. Penicillin G potassium salt is used to study murosomes of staphylococci1 and the penicillin-induced lysis of Streptococcus mutans2.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - 46609 external link
Biochem/physiol Actions
Mode of Action: Inhibits bacterial cell wall synthesis.Antimicrobial spectrum: Gram-positive bacteria
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Sigma Aldrich - 13750 external link
Biochem/physiol Actions
Mode of Action: Inhibits bacterial cell wall synthesis.Antimicrobial spectrum: Gram-positive bacteria
Sigma Aldrich - P8721 external link
Application
Use in cell culture in combination with streptomcyin and other antibiotics.
Biochem/physiol Actions
Inhibits the synthesis of bacterial cell walls by inhibition of the cell wall peptidoglycan chain cross-lining. Antimicrobial spectrum: Gram-positive bacteria
Mode of Action: Inhibits bacterial cell wall synthesis.Antimicrobial spectrum: Gram-positive bacteria
Reconstitution
溶液应过滤杀菌,在 2-8°C 下最长可储存一周,在 -20°C 下可长期储存。溶液在 37°C 下可稳定 3 天。
Toronto Research Chemicals - B288601 external link
An antibiotic substance produced by Penicillium sp. Antibacterial.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Chain, E., et al.: Lancet, 2, 226 (1929)
  • • Fleming, A., et al.: Br. J. Exp. Pathol., 10, 226 (1929)
  • • Clutterbuck, P.W., et al.: Biochem. J., et al.: 26, 1907 (1929)
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PATENTS

PATENTS

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INTERNET

INTERNET

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