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Cephalosporin C

AlkaPlorer ID: AK000222

Synonym: 'cephalosporin c', 'Cephalosporin C'

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

Structure

SMILES: CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1

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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

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InChIKey: HOKIDJSKDBPKTQ-GLXFQSAKSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 415.4240000000002

TPSA？: 176.32999999999998

MolLogP？: -1.129699999999996

Number of H-Donors: 4

Number of H-Acceptors: 8

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus cereus Beta-lactamase 1 Kcat 0.2 /s 10.1128/aac.00537-07
Enterococcus faecalis Enterococcus faecalis MIC 0.5 ug.mL-1 10.1021/acs.jmedchem.8b01093
Escherichia coli Escherichia coli MIC 16.0 ug.mL-1 10.1016/j.ejmech.2012.03.008
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 25918.5 nM None
Homo sapiens Chromobox protein homolog 1 Potency 44668.4 nM None
Homo sapiens Dopamine D1 receptor Potency 5804.5 nM None
Homo sapiens Flap endonuclease 1 Potency 23.8 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 37685.8 nM None
Salmonella enterica subsp. enterica serovar Typhimurium Salmonella typhimurium Ratio 1.0 None 10.1016/j.ejmech.2012.03.008
Staphylococcus aureus Staphylococcus aureus Activity 4.97 log10CFU 10.1021/acs.jmedchem.9b01832
Staphylococcus aureus Staphylococcus aureus Inhibition nan % 10.1021/acs.jmedchem.9b01832
Staphylococcus aureus Staphylococcus aureus MIC 1.0 ug.mL-1 10.1021/acs.jmedchem.8b01093
Trypanosoma brucei 6-phospho-1-fructokinase Potency 756.9 nM None
None Unchecked Potency 6309.6 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT004128 CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCCC(=O)C(=O)O)[C@H]2SC1.N[C@H](CCC(=O)O)C(=O)O>>CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1 CEPHALOSPORIN-C-TRANSAMINASE-RXN
AKRT004138 CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1.O=C(O)CCC(=O)C(=O)O>>CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCCC(=O)C(=O)O)[C@H]2SC1 R03063
AKRT004139 CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1.O=C(O)CCC(=O)C(=O)O>>N[C@H](CCC(=O)O)C(=O)O R03063
AKRT004140 CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1>>CC(=O)O R03062
AKRT004141 CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1>>CC(=O)O.N[C@H](CCCC(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CO)CS[C@H]12)C(=O)O None
AKRT004142 CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1>>CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1 enzymemap_76190
AKRT004143 CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1>>CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1.N[C@H](CCCC(=O)O)C(=O)O None
AKRT004144 CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1>>CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCCC(=O)C(=O)O)[C@H]2SC1 R07400
AKRT004145 CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1>>CC(=O)OCC1=C(C(=O)O)N[C@@H]([C@H](NC(=O)CCC[C@@H](N)C(=O)O)C(=O)O)SC1 enzymemap_78652
AKRT004146 CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1>>N[C@H](CCCC(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CO)CS[C@H]12)C(=O)O R03062
AKRT004147 CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1>>N[C@H](CCCC(=O)O)C(=O)O enzymemap_76190
AKRT004438 CC(=O)[32S].N[C@H](CCCC(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CO)CS[C@H]12)C(=O)O>>CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1 None
AKRT004708 CC(=O)[CoA].N[C@H](CCCC(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CO)CS[C@H]12)C(=O)O>>CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1 2.3.1.175-RXN