| General Information of MET (ID: META00723) |
| Name |
6-Oxopiperidine-2-carboxylic acid
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| Synonyms |
Click to Show/Hide Synonyms of This Metabolite
6-OPCA; 6-Oxopiperidine-2-carboxylate; Adipo-2,6-lactam; Cyclic a-aminoadipate; Cyclic a-aminoadipic acid; Cyclic alpha-aminoadipic acid
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| Structure Type |
Amino acids, peptides, and analogues (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Carboxylic acids and derivatives
Amino acids, peptides, and analogues
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| PubChem CID |
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| HMDB ID |
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| Formula |
C6H9NO3
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| Structure |
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3D MOL
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2D MOL
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Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
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| ChEBI ID |
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| Physicochemical Properties |
Molecular Weight |
143.14 |
Topological Polar Surface Area |
66.4 |
| XlogP |
-0.4 |
Complexity |
166 |
| Heavy Atom Count |
10 |
Rotatable Bond Count |
1 |
| Hydrogen Bond Donor Count |
2 |
Hydrogen Bond Acceptor Count |
3 |
| Function |
6-Oxopiperidine-2-carboxylic acid, also known as 6-Oxo-pipecolinic acid, or 6-Oxo-piperidine-2-carboxylic acid, is associated with penicillin V in the production on Penicillium chrysogenum fermentations. Analysis of a 13C NMR spectrum of a concentrated broth from Penicillium chrysogenum fermentation revealed the presence of penicillin V and 6-oxo-piperidine-2-carboxylic acid(1) as the principal constituents. The latter lactam, identical to an authentic sample prepared by the cyclization of alpha-aminoadipic acid was present to the extent of 28 mol% of penicillin V. The lactam isolated form the broth was nearly racemic, having a slight excess of the L-isomer. This isolation provides further evidence regarding the biosynthetic precursors of the hydrophobic penicillins. (PMID: 6788737
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Regulatory Network
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Induced Change
