Details of the Drug

General Information of Drug (ID: DMYW3ZG)

Drug Name

Cephalosporin C

Synonyms

cephalosporin C; 7-(5-Amino-5-carboxyvaleramido)cephalosporanic acid; 61-24-5; UNII-3XIY7HJT5L; CHEBI:15776; EINECS 200-501-6; 3XIY7HJT5L; BRN 0065348; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-7-((5-amino-5-carboxy-1-oxopentyl)amino)-8-oxo-, (6R-(6alpha,7beta(R*)))-; (6R,7R)-3-[(acetyloxy)methyl]-7-{[(5R)-5-amino-5-carboxypentanoyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(5-amino-5-carboxyvaleramid

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

415.4

Topological Polar Surface Area (xlogp)

-4.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C16H21N3O8S
IUPAC Name: (6R,7R)-3-(acetyloxymethyl)-7-[[(5R)-5-amino-5-carboxypentanoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Canonical SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CCC[C@H](C(=O)O)N)SC1)C(=O)O
InChI: InChI=1S/C16H21N3O8S/c1-7(20)27-5-8-6-28-14-11(13(22)19(14)12(8)16(25)26)18-10(21)4-2-3-9(17)15(23)24/h9,11,14H,2-6,17H2,1H3,(H,18,21)(H,23,24)(H,25,26)/t9-,11-,14-/m1/s1
InChIKey: HOKIDJSKDBPKTQ-GLXFQSAKSA-N

Cross-matching ID

PubChem CID: 65536
ChEBI ID: CHEBI:15776
CAS Number: 61-24-5
DrugBank ID: DB03313
TTD ID: D0O4TL

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial DD-carboxypeptidase (Bact vanYB)	TTLP6GN	VANY_ENTFA	Inhibitor	[1]
Bacterial Penicillin binding protein 3 (Bact mrcA)	TT85JMW	FTSI_ECOLI	Antagonist	[1]
Bacterial Penicillin-binding protein 1B (Bact mrcB)	TT329FH	PBPB_ECOLI	Antagonist	[1]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

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4	Genetic analyses of beta-lactamase negative ampicillin-resistant strains of Haemophilus influenzae isolated in Okinawa, Japan. Jpn J Infect Dis. 2006 Feb;59(1):36-41.
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6	Moxalactam (6059-S), a new 1-oxa-beta-lactam: binding affinity for penicillin-binding proteins of Escherichia coli K-12.
7	In vitro evaluation of E1040, a new cephalosporin with potent antipseudomonal activity. Antimicrob Agents Chemother. 1988 May;32(5):693-701.
8	Association of amino acid substitutions in penicillin-binding protein 3 with beta-lactam resistance in beta-lactamase-negative ampicillin-resistant Haemophilus influenzae. Antimicrob Agents Chemother. 2001 Jun;45(6):1693-9.
9	Mode of Action of the Monobactam LYS228 and Mechanisms Decreasing In Vitro Susceptibility in Escherichia coli and Klebsiella pneumoniae. Antimicrob Agents Chemother. 2018 Sep 24;62(10):e01200-18.
10	The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
11	Binding of cephalothin and cefotaxime to D-ala-D-ala-peptidase reveals a functional basis of a natural mutation in a low-affinity penicillin-binding protein and in extended-spectrum beta-lactamases. Biochemistry. 1995 Jul 25;34(29):9532-40.
12	Has nature already identified all useful antibacterial targets Curr Opin Microbiol. 2008 Oct;11(5):387-92.
13	A 1.2-A snapshot of the final step of bacterial cell wall biosynthesis. Proc Natl Acad Sci U S A. 2001 Feb 13;98(4):1427-31.
14	Extended-spectrum cephalosporinases: structure, detection and epidemiology. Future Microbiol. 2007 Jun;2:297-307.
15	How many modes of action should an antibiotic have Curr Opin Pharmacol. 2008 Oct;8(5):564-73.
16	Synthesis and evaluation of 3-(dihydroxyboryl)benzoic acids as D,D-carboxypeptidase R39 inhibitors. J Med Chem. 2009 Oct 8;52(19):6097-106.
17	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.