Compound
L-pipecolate
The zwitterion of L-pipecolic acid formed by proton transfer from the carboxy group to nitrogen; major species at pH 7.3.
Definition from ChEBI (CHEBI:61185), read 2026-09-23. CC BY 4.0.
Structure
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- Class
- Organic compound
- Formula
- C6H11NO2
- Mass
- 129.159 g/mol
- Charge
- 0
- InChIKey
- HXEACLLIILLPRG-YFKPBYRVSA-N
- SMILES
- [H][C@@]1(C(=O)[O-])CCCC[NH2+]1
- Look it up
- ChEBIPubChemBy InChIKey
Identity from ChEBI, geometry from PubChem. Not evidence.
What it touches on the way
Mechanistic reach
4 entities
4 entities reached.
0 reported hops4 assembled from the scaffold
What the reference databases state
Statements
7 statements
7 statements · 2 reference databases · Subject: L-pipecolate · Sources: Human-GEM, Rhea
- L-pipecolate is converted to L-lysineCompoundRhea RHEA:34303Inferred only
- L-lysine is converted to L-pipecolateCompoundRhea RHEA:34303Inferred only
- L-pipecolate is a substrate of PIPOXProteinHuman-GEM MAR08021Inferred only
- L-pipecolate is a substrate of PIPOXProteinRhea RHEA:11992Inferred only
- L-pipecolate is transported by SLC6A15ProteinRhea RHEA:71387Inferred only
- L-pipecolate is transported by SLC6A20ProteinRhea RHEA:71267Inferred only
- L-pipecolate is transported by SLC6A7ProteinRhea RHEA:71267Inferred only
Reactions
15 reactions
MAM01663x+proton+NADH(2-)L-pipecolate+NAD(+)
Reaction pageLeft to rightBalancedperoxisome
Human-GEM MAR08019CC BY 4.0Reference data
FAD+L-pipecolateMAM00556x+FADH2+proton
Catalysed by PIPOX
Reaction pageLeft to rightBalancedEC 1.5.3.1, 1.5.3.7peroxisome
Human-GEM MAR08021CC BY 4.0Reference data
Reaction pageReversibleBalance undeterminableextracellular space
Human-GEM MAR10255CC BY 4.0Reference data
L-pipecolate+sodium(1+)L-pipecolate+sodium(1+)
Reaction pageReversibleBalancedcytosol, extracellular space
Human-GEM MAR10384CC BY 4.0Reference data
L-pipecolate+sodium(1+)L-pipecolate+sodium(1+)
Reaction pageReversibleBalancedcytosol, peroxisome
Human-GEM MAR10385CC BY 4.0Reference data
L-pipecolate+dioxygenCHEBI:58769+hydrogen peroxide+hydron
Catalysed by PIPOX
Reaction pageDirection not assertedBalanced
Rhea RHEA:11992CC BY 4.0Reference data
L-pipecolate+NADP(3-)CHEBI:77631+NADPH(4-)+hydron
Catalysed by CRYM
Reaction pageRight to leftBalanced
Rhea RHEA:12524CC BY 4.0Reference data
L-pipecolate+ACHEBI:58769+AH2+hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:19777CC BY 4.0Reference data
L-pipecolate+NAD(1-)CHEBI:77631+NADH(2-)+hydron
Catalysed by CRYM
Reaction pageRight to leftBalanced
Rhea RHEA:30807CC BY 4.0Reference data
Reaction pageDirection not assertedBalanced
Rhea RHEA:34303CC BY 4.0Reference data
L-pipecolate+malonyl-CoA+2NADPH(4-)+4hydronCHEBI:167645+carbon dioxide+2NADP(3-)+coenzyme A(4-)+2water
Reaction pageDirection not assertedBalanced
Rhea RHEA:65392CC BY 4.0Reference data
L-pipecolate+malonyl-CoA+3NADPH(4-)+5hydronCHEBI:167675+carbon dioxide+3NADP(3-)+coenzyme A(4-)+2water
Reaction pageDirection not assertedBalanced
Rhea RHEA:67128CC BY 4.0Reference data
Where it reaches
1 system, 2 regions, 4 tissues, 4 transporter routes — routes, not measurements: transporters known to carry L-pipecolate are expressed there, and no source reports it arriving.
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Other names
2 names
Resolves to: L-pipecolate
- Also called
- (S)-2-carboxypiperidinium betaine
- Systematic name
- (2S)-piperidinium-2-carboxylate