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957-68-6 molecular structure
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(6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

ChemBase ID: 73065
Molecular Formular: C10H12N2O5S
Molecular Mass: 272.27768
Monoisotopic Mass: 272.04669249
SMILES and InChIs

SMILES:
N12[C@H](SCC(=C1C(=O)O)COC(=O)C)[C@@H](C2=O)N
Canonical SMILES:
CC(=O)OCC1=C(C(=O)O)N2[C@H](SC1)[C@@H](C2=O)N
InChI:
InChI=1S/C10H12N2O5S/c1-4(13)17-2-5-3-18-9-6(11)8(14)12(9)7(5)10(15)16/h6,9H,2-3,11H2,1H3,(H,15,16)/t6-,9-/m1/s1
InChIKey:
HSHGZXNAXBPPDL-HZGVNTEJSA-N

Cite this record

CBID:73065 http://www.chembase.cn/molecule-73065.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
IUPAC Traditional name
7β-aminocephalosporanic acid
Synonyms
(6R,7R)-3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
(7R)-7-Aminocephalosporanic Acid
3-(Acetoxymethyl)-7-aminocephem-4-carboxylic Acid
7-ACS
7β-Aminocephalosporanic Acid
7-Aminocephalosporinic acid
7-ACA
7-ACA
7-Aminocephalosporanic acid
7-Aminocephalosporanic acid
7-氨基头孢烷酸
CAS Number
957-68-6
EC Number
213-485-0
MDL Number
MFCD00005177
Beilstein Number
622637
622637, 8919572
PubChem SID
24851470
24846046
162037985
PubChem CID
441328
483168
CHEBI ID
2255
CHEMBL
1161449
Chemspider ID
390087
KEGG ID
C07756
MeSH Name
7-Aminocephalosporanic+acid
Wikipedia Title
7-ACA

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.4190428  H Acceptors
H Donor LogD (pH = 5.5) -3.8121455 
LogD (pH = 7.4) -4.088983  Log P -3.8148885 
Molar Refractivity 62.7384 cm3 Polarizability 24.72692 Å3
Polar Surface Area 109.93 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Apperance
White Solid expand Show data source
Melting Point
>260°C expand Show data source
>300 °C(lit.) expand Show data source
300°C expand Show data source
Partition Coefficient
-1.87 expand Show data source
Optical Rotation
[α]19/D +90°, c = 0.5 in KH2PO4/trace NaOH expand Show data source
pKa
2.59 expand Show data source
pKb
11.41 expand Show data source
Storage Condition
-20°C expand Show data source
Hygroscopic, -20°C Freezer, Under Inert Atmosphere 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
3 expand Show data source
Risk Statements
42/43 expand Show data source
R:22 expand Show data source
R42/43 expand Show data source
Safety Statements
22-36/37 expand Show data source
S:36/37/39 expand Show data source
S22 S36/37 expand Show data source
GHS Pictograms
GHS health hazard expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
317, 334 expand Show data source
H317-H334 expand Show data source
GHS Precautionary statements
261, 280, 342+311 expand Show data source
P261-P280-P342 + P311 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
~97% expand Show data source
~98% expand Show data source
≥95% (HPLC) expand Show data source
98% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Empirical Formula (Hill Notation)
C10H12N2O5S expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02150347 external link
Purity: Approx. 98%
Light yellow crystalline powder
Selleck Chemicals - S2530 external link
Research Area
Description Infection
Biological Activity
Description 7-Aminocephalosporanic acid is used for synthesis of cephalosporin antibiotics and intermediates.
Targets
IC50
In Vitro 7-Aminocephalosporanic acid is the basic building block used in the synthesis of many important semisynthetic cephalosporin antibiotics. 7-Aminocephalosporanic acid commonly appears as a white or whitish powder, is an important intermediate for the manufacture of the semisynthetic cephalosporin. 7-Aminocephalosporanic acid is an amphoteric compound. [1]
In Vivo
Clinical Trials
Features
References
[1] Wang S, et al. Ind Eng Chem Res, 2005, 44 (10), 3783–3787
Sigma Aldrich - 191140 external link
Packaging
5 g in glass bottle
Application
Potent inhibitor of bacterial (S. aureus) β-lactamase.1
Sigma Aldrich - 07300 external link
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 - A603415 external link
It is the starting material for semi-synthetic cephalosporins. Obtained by mild acid hydrolysis of cephalosporin C.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Wang S, et al. Ind Eng Chem Res, 2005, 44 (10), 3783–3787
  • • Matsuda, A., et al.: J. Bacteriol., 169, 5815 (1987)
  • • Aramori, I., et al.: J. Ferment. Bioeng., 72, 227 (1987)
  • • Park, S., et al.: J. Biosci. Bioeng., 94, 218 (1987)
  • • Takimoto, A., et al.: Appl. Microbiol. Biotechnol., 65, 263 (1987)
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PATENTS

PATENTS

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INTERNET

INTERNET

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