(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase ID: 67463
• Molecular Formular: C8H12N2O3S
• Molecular Mass: 216.25748
• Monoisotopic Mass: 216.05686325
• SMILES: C(=O)([C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)N)O
• Canonical SMILES: OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)N
• InChI: InChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1
• InChIKey: NGHVIOIJCVXTGV-ALEPSDHESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: aminopenicillanic acid; penin; (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Synonyms: 6-Aminopenicillanic acid; (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-APA; 6-APS; 6β-Aminopenicillanic acid; NSC 50071; [2S-(2α,5α,6β)]-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid; Phenacyl 6-Aminopenicillinate; (+)-6-Aminopenicillanic Acid; Phenacyl-6-Aminopenicillinate; Penicin; (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-APA; (+)-6-Aminopenicillanic acid; Aminopenicillanic acid; 6-Aminopenicillanic acid; (2S,5R,6R)-6-氨基-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸; (+)-6-氨基青霉烷酸; 6-氨基青霉烷酸

Database IDs

• CAS Number: 551-16-6
• EC Number: 208-993-4
• MDL Number: MFCD00005176
• Beilstein Number: 15080
• Merck Index: 14458
• PubChem SID: 24846248; 162033198; 24891174
• PubChem CID: 11082
• CHEBI ID: 57869
• Chemspider ID: 10611
• Wikipedia Title: 6-APA

CALCULATED PROPERTIES

• Acid pKa: 3.415152
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.8350077
• LogD (pH = 7.4): -3.1041005
• Log P: -2.8378367
• Molar Refractivity: 50.3621 cm^3
• Polarizability: 20.43413 Å^3
• Polar Surface Area: 83.63 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water (Sparingly)
• Apperance: White Solid
• Melting Point: 195-198°C (dec.); 198 - 200 °C; 198-200 °C (dec.)(lit.); 200°C dec.; 206 - 208 °C; 206-208 °C (dec.)
• Boiling Point: > 200 °C (decomposes)
• Auto Ignition Point: > 360 °C
• Density: 350 - 550 kg/m3 (bulk density)
• Optical Rotation: [α]20/D +275±10°, c = 1% in 0.1 M HCl; [α]22/D +276.3°, c = 1.2 in 0.1 M HCl; +275 (c=1 in 0.1N HCl)

Safety Information

• Storage Condition: 0°C; -20°C Freezer
• Storage Warning: IRRITANT
• RTECS: XH8225000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 42/43; R:36/37/38
• Safety Statements: 22-24-37-45; 22-36/37; S:20-25-26-37/39
• TSCA Listed: false; 是
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334; H334-H317
• GHS Precautionary statements: P261-P280-P342 + P311; P285-P261-P280-P302+P352-P321-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Lactamase inhibitor

Product Information

• Purity: ≥98.0% (S); 95+%; 96%; 98%
• Biological Source: Prod. by enzymic hydrol. of benzyl- or phenoxymethylpenicillins. Also prod. as metab. prod. of several penicillin-producing fungi, esp. when side-chain precursors are absent.
• Application(s): Antibiotic against; Proteus mirabilis, Escherichia coli and Staphylococcus aureus
• Empirical Formula (Hill Notation): C8H12N2O3S

DETAILS

MP Biomedicals - 02100631

Crystalline

Sigma Aldrich - A70909

Packaging
10, 50 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A70909.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 09070

Other Notes
Coupling to Sepharose® 4B for covalent affinity chromatography of penicillin-binding proteins1
Legal Information
Sepharose is a registered trademark of GE Healthcare

Toronto Research Chemicals - A618895

(+)-6-Aminopenicillanic Acid is the core structure in penicillins, obtained from the fermentation brew of the Penicillium mold. (+)-6-Aminopenicillanic Acid is used as the main starting block for the preparation of numerous semisynthetic penicillins.

REFERENCES

• Zel'tser, I.Z. et al.: Gig. Truda Prof. Zabol., 5, 59 (1983)
• Hamilton-Miller, J.M.T.: Int. J. Antimicrob. Agents, 31, 189 (1983)
• Novikova, N.D. et al.: Mikol. Fitopatol., 7, 101 (1983)
• Huber, F. et al., Cephalosporins Penicillins: Chem. Biol., (Flynn, E.H., Ed.), Academic Press, 1972, 27, (rev)
• Micetich, R.G. et al., Synthesis, 1976, 264, (oxide)
• Von Daehne, W. et al., J. Antibiot., 1980, 33, 451
• Moore, B.A. et al., Antimicrob. Agents Chemother., 1984, 20, 327, (props)
• Kirk-Othmer Encycl. Chem. Technol., 4th edn., Wiley, 1991, 3, 129, (rev)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PCU500
• Aldrich Library of NMR Spectra, 2nd edn., 1983, 1, 664A, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 791C, (ir)
• Batchelor, R. et al., Nature (London), 1959, 183, 257, (manuf)