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34632-04-7 molecular structure
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(7R)-7-[(2S)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

ChemBase ID: 163976
Molecular Formular: C16H17N3O4S
Molecular Mass: 347.38888
Monoisotopic Mass: 347.09397704
SMILES and InChIs

SMILES:
c1cccc(c1)[C@@H](C(=O)N[C@@H]1C(=O)N2C1SCC(=C2C(=O)O)C)N
Canonical SMILES:
N[C@@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2C1SCC(=C2C(=O)O)C
InChI:
InChI=1S/C16H17N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11+,15?/m0/s1
InChIKey:
ZAIPMKNFIOOWCQ-FEBOZLGHSA-N

Cite this record

CBID:163976 http://www.chembase.cn/molecule-163976.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(7R)-7-[(2S)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
IUPAC Traditional name
(7R)-7-[(2S)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Synonyms
(6R,7R)-7-[[(2S)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
[6R-[6α,7β(S*)]]-7-[(Aminophenylacetyl)amino]-3-methyl-8-oxo-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
7-(α-Amino-L-phenylacetamido)-3-deacetoxycephalosporanic Acid
L-Cephalexin
CAS Number
34632-04-7
PubChem SID
162258111
PubChem CID
44318507

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC C256805 external link Add to cart
PubChem 44318507 external link
Data Source Data ID Price
TRC
C256805 external link Add to cart Please log in.
Data Source Data ID
PubChem 44318507 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.4520106  H Acceptors
H Donor LogD (pH = 5.5) -2.1413963 
LogD (pH = 7.4) -2.3951817  Log P -2.145041 
Molar Refractivity 88.9736 cm3 Polarizability 34.625595 Å3
Polar Surface Area 112.73 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
MSDS Link
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Certificate of Analysis
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DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - C256805 external link
The L-diastereomer of the β-lactam antibiotic Cephalexin (C256800). It is is transported by PEPT1 (the oligopeptide transporter responsible for absorption of peptide nutrients in the small intestine) with high affinity, but is not metabolized by PEPT1 its

REFERENCES

REFERENCES

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  • • Mitsuoka, K. et al.: Biol. Pharmac. Bull., 32, 1459 (2009)
  • • Snyder, N.J. et al.: Antimicrob. Agents Chemother., 41, 1649 (2009)
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PATENTS

PATENTS

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INTERNET

INTERNET

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