ChemFOnt: Showing chemical card for 6-Oxopiperidine-2-carboxylic acid (CFc000042121)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:44:27 UTC

Chemfont ID

CFc000042121

Molecule Identification

Common Name

6-Oxopiperidine-2-carboxylic acid

Definition

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

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Adipo-2,6-lactam	ChEBI
Cyclic alpha-aminoadipic acid	ChEBI
Cyclic a-aminoadipate	Generator
Cyclic a-aminoadipic acid	Generator
Cyclic alpha-aminoadipate	Generator
Cyclic α-aminoadipate	Generator
Cyclic α-aminoadipic acid	Generator
6-Oxopiperidine-2-carboxylate	Generator
6-OPCA	HMDB

Chemical Formula

C₆H₉NO₃

Average Molecular Weight

143.1406

Monoisotopic Molecular Weight

143.058243159

IUPAC Name

6-hydroxy-2,3,4,5-tetrahydropyridine-2-carboxylic acid

Traditional Name

6-hydroxy-2,3,4,5-tetrahydropyridine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1CCCC(O)=N1

InChI Identifier

InChI=1S/C6H9NO3/c8-5-3-1-2-4(7-5)6(9)10/h4H,1-3H2,(H,7,8)(H,9,10)

InChI Key

FZXCPFJMYOQZCA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Piperidinecarboxylic acid
Delta-lactam
Piperidinone
Piperidine
Carboxamide group
Secondary carboxylic acid amide
Lactam
Azacycle
Organoheterocyclic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Feces (PMID: 27543620)

Source

Exogenous

Exogenous (HMDB: HMDB0061705)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	11.4 g/L	ALOGPS
logP	-0.45	ALOGPS
logP	0.37	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.8	ChemAxon
pKa (Strongest Basic)	1.18	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.89 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	33.21 m³·mol⁻¹	ChemAxon
Polarizability	13.59 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0061705

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3014237

PDB ID

Not Available

ChEBI ID

87998

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 6-Oxopiperidine-2-carboxylic acid (CFc000042121)

MOL for CFc000042121 (6-Oxopiperidine-2-carboxylic acid)

3D MOL for CFc000042121 (6-Oxopiperidine-2-carboxylic acid)

3D SDF for CFc000042121 (6-Oxopiperidine-2-carboxylic acid)

3D-SDF for CFc000042121 (6-Oxopiperidine-2-carboxylic acid)

PDB for CFc000042121 (6-Oxopiperidine-2-carboxylic acid)

3D PDB for CFc000042121 (6-Oxopiperidine-2-carboxylic acid)

SMILES for CFc000042121 (6-Oxopiperidine-2-carboxylic acid)

INCHI for CFc000042121 (6-Oxopiperidine-2-carboxylic acid)

Structure for CFc000042121 (6-Oxopiperidine-2-carboxylic acid)

3D Structure for CFc000042121 (6-Oxopiperidine-2-carboxylic acid)