Record Information |
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Version | 1.0 |
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Created at | 2020-09-11 15:49:02 UTC |
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Updated at | 2022-12-13 23:36:23 UTC |
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CannabisDB ID | CDB006322 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | trans-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 is a very strong basic compound (based on its pKa). 4-Hydroxyproline exists in all living species, ranging from bacteria to humans. Within humans, 4-hydroxyproline participates in a number of enzymatic reactions. In particular, 4-hydroxyproline and succinic acid can be biosynthesized from L-proline and oxoglutaric acid through the action of the enzyme prolyl 4-hydroxylase. In addition, 4-hydroxyproline can be converted into pyrroline hydroxycarboxylic acid; which is catalyzed by the enzyme proline dehydrogenase 1, mitochondrial. In humans, 4-hydroxyproline is involved in the metabolic disorder called hyperornithinemia with gyrate atrophy (hoga). 4-Hydroxyproline is a potentially toxic compound. 4-Hydroxyproline, with regard to humans, has been found to be associated with several diseases such as periodontal probing depth, colorectal cancer, and alzheimer's disease; 4-hydroxyproline has also been linked to several inborn metabolic disorders including iminoglycinuria and hydroxyprolinemia. An optically active form of 4-hydroxyproline having L-trans-configuration. |
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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 | (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid |
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Traditional Name | hypro |
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CAS Registry Number | Not Available |
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SMILES | O[C@H]1CN[C@@H](C1)C(O)=O |
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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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Not Available | Physical Properties |
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State | Not Available |
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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 | [] |
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Spectra |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-00ku-9000000000-f5bd67093b2f30a6f62b | 2018-05-25 | View Spectrum | GC-MS | trans-Hydroxyproline, non-derivatized, GC-MS Spectrum | splash10-000x-0950000000-5b1c397e26b28e872d20 | Spectrum | GC-MS | trans-Hydroxyproline, non-derivatized, GC-MS Spectrum | splash10-000x-0950000000-c46b5bba0f41001e3c18 | Spectrum | GC-MS | trans-Hydroxyproline, 3 TMS, GC-MS Spectrum | splash10-00di-9530000000-00db00b15ab5341d7d64 | Spectrum | GC-MS | trans-Hydroxyproline, 2 TMS, GC-MS Spectrum | splash10-0a4i-1900000000-c0a869abe2f1e9f8c08e | Spectrum | GC-MS | trans-Hydroxyproline, 3 TMS, GC-MS Spectrum | splash10-001l-1960000000-abcd0377696d2b52d815 | Spectrum | GC-MS | trans-Hydroxyproline, non-derivatized, GC-MS Spectrum | splash10-001i-0590000000-75e03328fb2d44469057 | Spectrum | GC-MS | trans-Hydroxyproline, non-derivatized, GC-MS Spectrum | splash10-000x-0950000000-c46b5bba0f41001e3c18 | Spectrum | GC-MS | trans-Hydroxyproline, non-derivatized, GC-MS Spectrum | splash10-00di-9530000000-00db00b15ab5341d7d64 | Spectrum | GC-MS | trans-Hydroxyproline, non-derivatized, GC-MS Spectrum | splash10-0a4i-1900000000-c0a869abe2f1e9f8c08e | Spectrum | GC-MS | trans-Hydroxyproline, non-derivatized, GC-MS Spectrum | splash10-001l-1960000000-abcd0377696d2b52d815 | Spectrum | GC-MS | trans-Hydroxyproline, non-derivatized, GC-MS Spectrum | splash10-000x-0940000000-97328204c6b60a244616 | Spectrum | GC-MS | trans-Hydroxyproline, non-derivatized, GC-MS Spectrum | splash10-000x-0940000000-468aeb79950a9e6dadc6 | Spectrum | GC-MS | trans-Hydroxyproline, non-derivatized, GC-MS Spectrum | splash10-0a4i-0900000000-40c0bfa9451caacaf422 | Spectrum | Predicted GC-MS | trans-Hydroxyproline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a6r-9100000000-af92b4a861832ca4ec13 | Spectrum | Predicted GC-MS | trans-Hydroxyproline, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-02mu-9670000000-81c8390bdfa262fa9b2f | Spectrum | Predicted GC-MS | trans-Hydroxyproline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | trans-Hydroxyproline, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | trans-Hydroxyproline, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | trans-Hydroxyproline, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | trans-Hydroxyproline, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | trans-Hydroxyproline, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | trans-Hydroxyproline, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | trans-Hydroxyproline, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | trans-Hydroxyproline, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | trans-Hydroxyproline, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0019-9700000000-ea3ed008938a57d1263c | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-014r-9000000000-0b76109525f362b600a0 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014l-9000000000-477e41e40831316e68ac | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0019-9300000000-7228a10f32d447b58ee0 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-001i-0900000000-11800ca52c6e911f8313 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-001i-0900000000-11800ca52c6e911f8313 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-001i-1900000000-b6bba00a324b6eab209f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-001i-1900000000-ba9df49a4d967cf8851d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , positive | splash10-000i-9000000000-6d125b0bb59101e9ce53 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0019-9300000000-7228a10f32d447b58ee0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-0019-9600000000-5bcced64c9dfeb96876f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-0019-9600000000-b575fa8df5e2d8bb3a99 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-014l-9000000000-c036fd15ccf6ed0c554e | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-00kr-9000000000-8746de5249187bab94dc | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-014i-9000000000-3f70e8e1eef8568e87ef | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-000i-9200000000-cd32fa744ef013f5ca48 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-000i-9200000000-3ea6a86203c48888d528 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-02tc-9000000000-95aa07d1970d7f83f347 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-014r-9000000000-95b2178b5433b4b2db50 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-3900000000-a10576d40ff1d7fc707a | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-02t9-9400000000-8b66308781907cdf6304 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014i-9000000000-7f9d42864b2decdbdd1d | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-2900000000-bfc9154f784caa2e61a7 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-02ar-9800000000-750b3fd4f0e1dcb8ef4c | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00r6-9000000000-efe39f47f6ee937ded3d | 2016-09-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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Pathways |
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Pathways | Not Available |
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Protein Targets |
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Enzymes | Not Available |
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Transporters | Not Available |
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Metal Bindings | Not Available |
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Receptors | Not Available |
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Transcriptional Factors | Not Available |
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Concentrations Data |
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Alien Dawg | Detected and Quantified | 0.00216 mg/g dry wt | | details | Gabriola | Detected and Quantified | 0.00344 mg/g dry wt | | details | Island Honey | Detected and Quantified | 0.00445 mg/g dry wt | | details | Quadra | Detected and Quantified | 0.00327 mg/g dry wt | | details | Sensi Star | Detected and Quantified | 0.00304 mg/g dry wt | | details | Tangerine Dream | Detected and Quantified | 0.00380 mg/g dry wt | | 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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FoodDB 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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General References | Not Available |
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