cephalexin   Click here for help

GtoPdb Ligand ID: 4832

Synonyms: cefalexin | Ceporex® | Keflex®
Approved drug
cephalexin is an approved drug (FDA (1971, prior history not available))
Compound class: Synthetic organic
Comment: Cephalexin is a cephalosporin antibacterial.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 138.03
Molecular weight 347.09
XLogP -2.19
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES NC(c1ccccc1)C(=O)NC1C(=O)N2C1SCC(=C2C(=O)O)C
Isomeric SMILES N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=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-/m1/s1
InChI Key ZAIPMKNFIOOWCQ-UEKVPHQBSA-N
References
1. Anand BS, Patel J, Mitra AK. (2003)
Interactions of the dipeptide ester prodrugs of acyclovir with the intestinal oligopeptide transporter: competitive inhibition of glycylsarcosine transport in human intestinal cell line-Caco-2.
J Pharmacol Exp Ther, 304 (2): 781-91. [PMID:12538834]
2. Covitz KM, Amidon GL, Sadée W. (1996)
Human dipeptide transporter, hPEPT1, stably transfected into Chinese hamster ovary cells.
Pharm Res, 13 (11): 1631-4. [PMID:8956326]
3. Fujimoto Y, Ishizaka Y, Tahira T, Sone H, Takahashi H, Enomoto K, Mori M, Sugimura T, Nagao M. (1991)
Possible involvement of c-myc but not ras genes in hepatocellular carcinomas developing after spontaneous hepatitis in LEC rats.
Mol Carcinog, 4 (4): 269-74. [PMID:1714740]
4. Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH. (1995)
Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2.
J Biol Chem, 270 (43): 25672-7. [PMID:7592745]
5. Luckner P, Brandsch M. (2005)
Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1.
Eur J Pharm Biopharm, 59 (1): 17-24. [PMID:15567297]
6. Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K. (2007)
Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters.
Biochem Pharmacol, 74 (2): 359-71. [PMID:17509534]
7. Terada T, Saito H, Mukai M, Inui K. (1997)
Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells.
Am J Physiol, 273 (5 Pt 2): F706-11. [PMID:9374833]
8. Terada T, Saito H, Mukai M, Inui KI. (1996)
Identification of the histidine residues involved in substrate recognition by a rat H+/peptide cotransporter, PEPT1.
FEBS Lett, 394 (2): 196-200. [PMID:8843163]