4-Hydroxyproline
Basic information
- CAS
18610-59-8- Standard SMILES
O=C(O)C1CC(O)CN1- InChIKey
PMMYEEVYMWASQN-UHFFFAOYSA-N- Molecular formula
- C5H9NO3
- Average molar mass
- 131.13 g/mol
- Monoisotopic mass
- 131.05824315
Overview
4-hydroxyproline is a monohydroxyproline where the hydroxy group is located at the 4-position. It is found in fibrillar collagen. It has a role as a human metabolite. It is a conjugate acid of a 4-hydroxyprolinate. It is a tautomer of a 4-hydroxyproline zwitterion.
Names & identifiers
- Preferred name
- 4-Hydroxyproline
- IUPAC
- 4-hydroxypyrrolidine-2-carboxylic acid
- English name
- 4-hydroxypyrrolidine-2-carboxylic acid
- Molecular formula
- C5H9NO3
- Molecular weight
- 131.13
Names & synonyms
4-hydroxypyrrolidine-2-carboxylic acid4-hydroxyproline6912-67-0CHEBI:20392DTXSID60861573RefChem:1070835DTXCID90218793trans-L-4-hydroxyproline4-Hydroxy-DL-prolineMFCD00066718SCHEMBL2279225249-07-4
Show more names
Nsc206304rel-(2S,4S)-4-Hydroxypyrrolidine-2-carboxylic acid
L-AllohydroxyprolineL-Proline, 4-hydroxy-, labeled with tritium, trans-4-Hydroxy-L-proline30724-02-8MB00510PB47459Proline, 4-hydroxy-EN300-17169
Database identifiers
- CAS
18610-59-8、25249-07-4、2584-71-6、3398-22-9、49761-17-3、618-27-9、6912-67-0- PubChem CID
- 825
- DTXSID
DTXSID60861573- ChEMBL
CHEMBL1213475- ChEBI
CHEBI:20392- Nikkaji
- J4.116E
Properties
Computed structural properties
- XLogP
- -3.3
- Topological polar surface area
- 69.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 125
Experimental & physicochemical properties
DrugsPharmaceuticals
Physicochemical properties
- Boiling point
- 355.233 · 355.233±42.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.395 · 1.395±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 2.14 · 2.140±0.40(predicted)
- HS Code
- 2933990099 · 2933990099
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- hs_code
- 2933990099
Chemistry & industry
Uses & manufacturing
UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Additional notes
DefinitionChEBI: 4-hydroxyproline is a monohydroxyproline where the hydroxy group is located at the 4-position. It is found in fibrillar collagen. It has a role as a human metabolite. It is a conjugate acid of a 4-hydroxyprolinate. It is a tautomer of a 4-hydroxyproline zwitterion.
Related reactions
45 records
Compound notes
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