Compound
trans-4-hydroxy-L-proline
An L-α-amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of trans-4-hydroxy-L-proline; major species at pH 7.3.
Definition from ChEBI (CHEBI:58375), read 2026-09-23. CC BY 4.0.
Structure
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- Class
- Organic compound
- Formula
- C5H9NO3
- Mass
- 131.131 g/mol
- Charge
- 0
- InChIKey
- PMMYEEVYMWASQN-DMTCNVIQSA-N
- SMILES
- O=C([O-])[C@@H]1C[C@@H](O)C[NH2+]1
- Look it up
- ChEBIPubChemBy InChIKey
Identity from ChEBI, geometry from PubChem. Not evidence.
What it touches on the way
Mechanistic reach
2 entities
2 entities reached.
0 reported hops2 assembled from the scaffold
What the reference databases state
Statements
8 statements
8 statements · 1 reference database · Subject: trans-4-hydroxy-L-proline · Sources: Rhea
- (S)-1-pyrroline-5-carboxylate is converted to trans-4-hydroxy-L-prolineCompoundRhea RHEA:54644Inferred only
- trans-4-hydroxy-L-proline is converted to (S)-1-pyrroline-5-carboxylateCompoundRhea RHEA:54644Inferred only
- L-proline is converted to trans-4-hydroxy-L-prolineCompoundRhea RHEA:51508Inferred only
- trans-4-hydroxy-L-proline is converted to L-prolineCompoundRhea RHEA:51508Inferred only
- trans-4-hydroxy-L-proline is a substrate of PRODH2ProteinRhea RHEA:52512Inferred only
- trans-4-hydroxy-L-proline is transported by SLC1A4ProteinRhea RHEA:84335Inferred only
- trans-4-hydroxy-L-proline is transported by SLC1A4ProteinRhea RHEA:84339Inferred only
- trans-4-hydroxy-L-proline is transported by SLC1A4ProteinRhea RHEA:84331Inferred only
Reactions
8 reactions
trans-4-hydroxy-L-prolineCHEBI:57690
Reaction pageDirection not assertedBalanced
Rhea RHEA:21152CC BY 4.0Reference data
L-proline+2-oxoglutarate(2-)+dioxygentrans-4-hydroxy-L-proline+succinate(2-)+carbon dioxide
Reaction pageDirection not assertedBalanced
Rhea RHEA:51508CC BY 4.0Reference data
trans-4-hydroxy-L-proline+a quinone(3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate+a quinol+hydron
Catalysed by PRODH2
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:52512CC BY 4.0Reference data
coenzyme Q10+trans-4-hydroxy-L-proline(3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate+ubiquinol-10+hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:52516CC BY 4.0Reference data
trans-4-hydroxy-L-proline(S)-1-pyrroline-5-carboxylate+water+hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:54644CC BY 4.0Reference data
trans-4-hydroxy-L-proline+L-seryl residue+sodium(1+)trans-4-hydroxy-L-proline+L-seryl residue+sodium(1+)
Transported by SLC1A4
Reaction pageDirection not assertedBalanced
Rhea RHEA:84331CC BY 4.0Reference data
trans-4-hydroxy-L-proline+L-alanine+sodium(1+)trans-4-hydroxy-L-proline+L-alanine+sodium(1+)
Transported by SLC1A4
Reaction pageDirection not assertedBalanced
Rhea RHEA:84335CC BY 4.0Reference data
trans-4-hydroxy-L-proline+L-threonine+sodium(1+)trans-4-hydroxy-L-proline+L-threonine+sodium(1+)
Transported by SLC1A4
Reaction pageDirection not assertedBalanced
Rhea RHEA:84339CC BY 4.0Reference data
Where it reaches
8 systems, 14 regions, 30 tissues, 30 transporter routes — routes, not measurements: transporters known to carry trans-4-hydroxy-L-proline are expressed there, and no source reports it arriving.
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Other names
2 names
Resolves to: trans-4-hydroxy-L-proline
- Also called
- hydroxyproline zwitterion
- Systematic name
- (2S,4R)-4-hydroxypyrrolidinium-2-carboxylate