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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:35:32 UTC |
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Update Date | 2020-06-04 20:47:59 UTC |
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BMDB ID | BMDB0000725 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Hydroxyproline |
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Description | 4-Hydroxyproline, also known as Hyp or oxaceprol, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 4-Hydroxyproline is a drug which is used in france as a combination product for the treatment of small, superficial wounds. 4-Hydroxyproline exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. 4-Hydroxyproline exists in all living species, ranging from bacteria to humans. 4-Hydroxyproline is a potentially toxic compound. 4-Hydroxyproline has been found to be associated with several diseases known as ulcerative colitis, hemodialysis, crohn's disease, and alzheimer's disease; also 4-hydroxyproline has been linked to the inborn metabolic disorders including iminoglycinuria. |
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Structure | |
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Synonyms | Value | Source |
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(2S,4R)-4-Hydroxy-2-pyrrolidinecarboxylic acid | ChEBI | (2S,4R)-trans-4-Hydroxyproline | ChEBI | delta-Hydroxyproline | ChEBI | Hydroxy-L-proline | ChEBI | Hydroxyproline | ChEBI | Hyp | ChEBI | Hypro | ChEBI | L-4-Hydroxyproline | ChEBI | L-Threo-4-hydroxyproline | ChEBI | trans-Hydroxyproline | ChEBI | trans-L-Hydroxyproline | ChEBI | L-Hydroxyproline | Kegg | trans-4-Hydroxy-L-proline | Kegg | (2S,4R)-4-Hydroxy-2-pyrrolidinecarboxylate | Generator | Δ-hydroxyproline | Generator | (2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid | HMDB | (4R)-4-Hydroxy-L-proline | HMDB | 4-Hydroxy-2-pyrrolidinecarboxylic acid | HMDB | 4-Hydroxy-L-proline | HMDB | 4-L-Hydroxyproline | HMDB | Hydroxiproline | HMDB | Hydroxy-proline | HMDB | LS-Hydroxyproline | HMDB | Oxaceprol | HMDB | trans-4-Hydroxyproline | HMDB | 4 Hydroxyproline | HMDB | Oxyproline | HMDB | (-)-4-Hydroxy-2-pyrrolidinecarboxylic acid | HMDB | (2S,4R)-(-)-4-Hydroxyproline | HMDB | (2S,4R)-4-Hydroxyproline | HMDB | (R)-4-Hydroxy-(S)-proline | HMDB | (R)-4-Hydroxy-L-proline | HMDB | (S)-Hydroxyproline | HMDB | 4(R)-Hydroxy-2(S)-pyrrolidinecarboxylic acid | HMDB | 4(R)-Hydroxyproline | HMDB | 4-Hydroxy-(S)-proline | HMDB | 4-trans-Hydroxy-L-proline | HMDB | L-Hypro | HMDB | L-trans-4-Hydroxyproline | HMDB | NSC 46704 | HMDB | trans-L-4-Hydroxyproline | HMDB | 4-Hydroxyproline | HMDB |
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Chemical Formula | C5H9NO3 |
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Average Molecular Weight | 131.1299 |
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Monoisotopic Molecular Weight | 131.058243159 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 51-35-4 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1 |
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InChI Key | PMMYEEVYMWASQN-DMTCNVIQSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Proline and derivatives |
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Alternative Parents | |
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Substituents | - Proline or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Pyrrolidine carboxylic acid
- Pyrrolidine carboxylic acid or derivatives
- Pyrrolidine
- 1,2-aminoalcohol
- Amino acid
- Secondary alcohol
- Carboxylic acid
- Secondary aliphatic amine
- Monocarboxylic acid or derivatives
- Azacycle
- Secondary amine
- Organoheterocyclic compound
- Organooxygen compound
- Organonitrogen compound
- Alcohol
- Organic nitrogen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organic oxygen compound
- Amine
- Carbonyl group
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Status | Detected and Quantified |
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Origin | Not Available |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | - Cytoplasm
- Endoplasmic reticulum
- Mitochondria
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | Not Available |
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Spectra |
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Spectra | |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Endoplasmic reticulum
- Mitochondria
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Biospecimen Locations | - Blood
- Epidermis
- Fibroblasts
- Kidney
- Liver
- Longissimus Thoracis Muscle
- Milk
- Pancreas
- Placenta
- Platelet
- Prostate Tissue
- Ruminal Fluid
- Semimembranosus Muscle
- Spleen
- Testis
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 23.4 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 25 +/- 5 uM | Not Specified | Not Specified | Normal | | details | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected and Quantified | 51 +/- 13 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Longissimus Thoracis Muscle | Detected and Quantified | 32 +/- 11 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 5.1 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 4.6 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 4.9 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 5.1 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Pancreas | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Platelet | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 2 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Semimembranosus Muscle | Detected and Quantified | 31 +/- 11 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Spleen | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 43 +/- 12 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 14.8 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy negative | | details | Blood | Detected and Quantified | 19.3 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy positive | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Sub/clinical ketosis | | details |
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External Links |
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HMDB ID | HMDB0000725 |
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DrugBank ID | DB08847 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB013511 |
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KNApSAcK ID | C00001370 |
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Chemspider ID | 5605 |
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KEGG Compound ID | C01157 |
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BioCyc ID | 4-HYDROXY-L-PROLINE |
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BiGG ID | 36935 |
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Wikipedia Link | Hydroxyproline |
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METLIN ID | 257 |
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PubChem Compound | 5810 |
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PDB ID | Not Available |
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ChEBI ID | 18095 |
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References |
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Synthesis Reference | Adams, Elijah; Goldstone, Alfred. Hydroxyproline metabolism. II. Enzymic preparation and properties of D1-pyrroline-3-hydroxy-5-carboxylic acid. Journal of Biological Chemistry (1960), 235 3492-8. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
- Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals (2009). Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics.
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
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