| Common Name |
3-Hydroxy-L-proline
| Description |
Constituent of collagen and the antibiotic Telomycin (Combined Chemical Dictionary).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
cis-3-Hydroxy-D-prolineChEBI
Procollagen trans-3-hydroxy-L-prolineHMDB
| Chemical Formlia |
C5H9NO3
| Average Molecliar Weight |
131.1299
| Monoisotopic Molecliar Weight |
131.058243159
| IUPAC Name |
(2R,3S)-3-hydroxypyrrolidine-2-carboxylic acid
| Traditional Name |
3-hydroxy-L-proline
| CAS Registry Number |
4298-08-2
| SMILES |
O[C@H]1CCN[C@H]1C(O)=O
| InChI Identifier |
InChI=1S/C5H9NO3/c7-3-1-2-6-4(3)5(8)9/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m0/s1
| InChI Key |
BJBUEDPLEOHJGE-IUYQGCFVSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as proline and derivatives. These are compounds containing proline or a derivative thereof resliting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic acids and derivatives
| Sub Class |
Carboxylic acids and derivatives
| Direct Parent |
Proline and derivatives
| Alternative Parents |
D-alpha-amino acids
Pyrrolidine carboxylic acids
Beta hydroxy acids and derivatives
Secondary alcohols
Amino acids
Monocarboxylic acids and derivatives
Dialkylamines
Carboxylic acids
Azacyclic compounds
Organopnictogen compounds
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Proline or derivatives
Alpha-amino acid
D-alpha-amino acid
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Beta-hydroxy acid
Hydroxy acid
Pyrrolidine
Amino acid
Secondary alcohol
Carboxylic acid
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Organic oxide
Organonitrogen compound
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organopnictogen compound
Aliphatic heteromonocyclic compound
| Molecliar Framework |
Aliphatic heteromonocyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Protein synthesis, amino acid biosynthesis
| Application |
Not Available
| Cellliar locations |
Not Available
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point235 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility431.0 mg/mLALOGPS
logP-3.2ALOGPS
logP-3.7ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)1.61ChemAxon
pKa (Strongest Basic)10.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity29.38 m3·mol-1ChemAxon
Polarizability12.16 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Not Available
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB011875
| KNApSAcK ID |
Not Available
| Chemspider ID |
9312313
| KEGG Compound ID |
C04397
| BioCyc ID |
3-HYDROXY-L-PROLINE
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB02113
| Metagene Link |
HMDB02113
| METLIN ID |
6494
| PubChem Compound |
11137200
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Dimetridazole
References |
| Synthesis Reference |
Sinha, Surajit; Tilve, Santosh; Chandrasekaran, Srinivasan. A convenient synthesis of trans-3-hydroxy-L-proline. ARKIVOC (Gainesville, FL, United States) (2005), (11), 209-217. |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
Not Available |
Enzymes
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Basement membrane-associated chondroitin sulfate proteoglycan (CSPG). Has prolyl 3-hydroxylase activity catalyzing the post-translational formation of 3-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens, especially types IV and V. May be involved in the secretory pathway of cells. Has growth suppressive activity in fibroblasts.
- Gene Name:
- LEPRE1
- Uniprot ID:
- Q32P28
- Molecular weight:
- 78921.41
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Shows prolyl 3-hydroxylase activity catalyzing the post-translational formation of 3-hydroxyproline in -Xaa-Pro-Gly-sequences in collagens, especially types II, IV and V (By similarity).
- Gene Name:
- LEPREL1
- Uniprot ID:
- Q8IVL5
- Molecular weight:
- 60386.32
- General function:
- Involved in iron ion binding
- Specific function:
- Has prolyl 3-hydroxylase activity catalyzing the post-translational formation of 3-hydroxyproline in -Xaa-Pro-Gly-sequences in collagens, especially types IV and V (By similarity).
- Gene Name:
- LEPREL2
- Uniprot ID:
- Q8IVL6
- Molecular weight:
- 81835.705
PMID: 18162180