CAS 551-16-6|6-Aminopenicillanic acid|(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid|aminopenicillanic acid|(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-...

General Information

Structure

Molecular Formula

C₈H₁₂N₂O₃S

Molecular Mass

216.25748

Exact Mass

216.05686325

Charge

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

Canonic Smiles

OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)N

Isomeric Smiles

C(=O)([C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)N)O

Calculated Properties

JChem

Acid pKa

3.415152

H Acceptors

H Donor

LogD (pH = 5.5)

-2.8350077

LogD (pH = 7.4)

-3.1041005

Log P

-2.8378367

Molar Refractivity

50.3621

Polarizability

20.43413

Polar Surface Area

83.63

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

6-Aminopenicillanic acid(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid6-APA6-APA(+)-6-氨基青霉烷酸(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-Aminopenicillanic acid(2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidPhenacyl-6-AminopenicillinatePenicinAminopenicillanic acid[2S-(2α,5α,6β)]-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic AcidNSC 500716β-Aminopenicillanic acidPhenacyl 6-Aminopenicillinate6-APS(+)-6-Aminopenicillanic Acid6-Aminopenicillanic acid6-氨基青霉烷酸

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

Names and Identifiers

Registration numbers

CAS Number

551-16-6

MDL Number

MFCD00005176

PubChem SID

2484624816203319824891174

EC Number

Beilstein Number

Merck Index

Wikipedia Title

PubChem CID

CHEBI ID

Chemspider ID

Registration numbers

Properties

Pharmacology Properties

Lactamase inhibitor

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Crystalline

6-APA

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.

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

TRC

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.

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

• Von Daehne, W. et al., J. Antibiot., 1980, 33, 451

• Micetich, R.G. et al., Synthesis, 1976, 264, (oxide)

• Moore, B.A. et al., Antimicrob. Agents Chemother., 1984, 20, 327, (props)

• Huber, F. et al., Cephalosporins Penicillins: Chem. Biol., (Flynn, E.H., Ed.), Academic Press, 1972, 27, (rev)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PCU500

• Kirk-Othmer Encycl. Chem. Technol., 4th edn., Wiley, 1991, 3, 129, (rev)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 791C, (ir)

• Batchelor, R. et al., Nature (London), 1959, 183, 257, (manuf)

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 1, 664A, (nmr)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

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

Registration numbers

CAS Number

551-16-6

MDL Number

MFCD00005176

PubChem SID

2484624816203319824891174

EC Number

Beilstein Number

Merck Index

Wikipedia Title

PubChem CID

CHEBI ID

Chemspider ID

Molecule Details

Crystalline

6-APA

A70909

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

TRC

A618895

References

PubChem Literature

From Data Sources

• 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)

• Von Daehne, W. et al., J. Antibiot., 1980, 33, 451

• Micetich, R.G. et al., Synthesis, 1976, 264, (oxide)

• Moore, B.A. et al., Antimicrob. Agents Chemother., 1984, 20, 327, (props)

• Huber, F. et al., Cephalosporins Penicillins: Chem. Biol., (Flynn, E.H., Ed.), Academic Press, 1972, 27, (rev)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PCU500

• Kirk-Othmer Encycl. Chem. Technol., 4th edn., Wiley, 1991, 3, 129, (rev)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 791C, (ir)

• Batchelor, R. et al., Nature (London), 1959, 183, 257, (manuf)

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 1, 664A, (nmr)

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Lactamase inhibitor

Molecule

ID:67463