Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2021-09-24 12:27:43 UTC |
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Update Date | 2022-07-12 15:36:35 UTC |
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HMDB ID | HMDB0304793 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | 4-Oxoproline |
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Description | 4-oxoproline 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-oxoproline is a substrate for the enzyme known as 4-oxoproline reductase. This enzyme converts 4-oxoproline (using NADH and a hydrogen ion) to cis-4-hydroxyproline. In 2022 the enzyme 4-oxo-L-proline reductase was identified as 3-hydroxybutyrate dehydrogenase 2 (BDH2) (PMID: 35150746 ). 4-oxoproline has been identified in human blood as reported by (PMID: 31557052 ). 4-Oxoproline is a poorly studied analog of L-proline. The only known natural compound containing a 4-oxoproline moiety is the antibiotic X-type actinomycin produced by Streptomyces antibioticus. Nevertheless, 4-oxoproline has been detected occasionally in various biological samples, including extracts of human embryonic kidney 293T (HEK293T) cells and the blood samples of type 2 diabetes patients treated with metformin, sulphonylurea, or both drugs combined (PMID: 35150746 ). |
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Structure | InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h4,6H,1-2H2,(H,8,9)/p-1 |
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Synonyms | Value | Source |
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4-Oxoprolinic acid | HMDB | 4-Ketoproline, (L)-isomer | HMDB | 4-Ketoproline | HMDB | 4-oxo-L-Proline | HMDB |
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Chemical Formula | C5H6NO3 |
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Average Molecular Weight | 128.108 |
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Monoisotopic Molecular Weight | 128.035316637 |
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IUPAC Name | 4-oxopyrrolidine-2-carboxylate |
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Traditional Name | 4-oxoprolinate |
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CAS Registry Number | Not Available |
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SMILES | [O-]C(=O)C1CC(=O)CN1 |
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InChI Identifier | InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h4,6H,1-2H2,(H,8,9)/p-1 |
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InChI Key | HFXAFXVXPMUQCQ-UHFFFAOYSA-M |
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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
- Oxoproline
- Pyrrolidine carboxylic acid
- Pyrrolidine carboxylic acid or derivatives
- Pyrrolidone
- 3-pyrrolidone
- Pyrrolidine
- Ketone
- Amino acid
- Cyclic ketone
- Carboxylic acid
- Secondary aliphatic amine
- Monocarboxylic acid or derivatives
- Azacycle
- Organoheterocyclic compound
- Secondary amine
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Amine
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Organic nitrogen compound
- Organic anion
- 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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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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4-Oxoproline,1TMS,isomer #1 | C[Si](C)(C)OC1=CNC(C(=O)[O-])C1 | 1467.9 | Semi standard non polar | 33892256 | 4-Oxoproline,1TMS,isomer #1 | C[Si](C)(C)OC1=CNC(C(=O)[O-])C1 | 1399.8 | Standard non polar | 33892256 | 4-Oxoproline,1TMS,isomer #1 | C[Si](C)(C)OC1=CNC(C(=O)[O-])C1 | 2310.5 | Standard polar | 33892256 | 4-Oxoproline,1TMS,isomer #2 | C[Si](C)(C)OC1=CC(C(=O)[O-])NC1 | 1365.0 | Semi standard non polar | 33892256 | 4-Oxoproline,1TMS,isomer #2 | C[Si](C)(C)OC1=CC(C(=O)[O-])NC1 | 1362.2 | Standard non polar | 33892256 | 4-Oxoproline,1TMS,isomer #2 | C[Si](C)(C)OC1=CC(C(=O)[O-])NC1 | 2138.9 | Standard polar | 33892256 | 4-Oxoproline,1TMS,isomer #3 | C[Si](C)(C)N1CC(=O)CC1C(=O)[O-] | 1307.4 | Semi standard non polar | 33892256 | 4-Oxoproline,1TMS,isomer #3 | C[Si](C)(C)N1CC(=O)CC1C(=O)[O-] | 1340.0 | Standard non polar | 33892256 | 4-Oxoproline,1TMS,isomer #3 | C[Si](C)(C)N1CC(=O)CC1C(=O)[O-] | 1829.1 | Standard polar | 33892256 | 4-Oxoproline,2TMS,isomer #1 | C[Si](C)(C)OC1=CN([Si](C)(C)C)C(C(=O)[O-])C1 | 1508.7 | Semi standard non polar | 33892256 | 4-Oxoproline,2TMS,isomer #1 | C[Si](C)(C)OC1=CN([Si](C)(C)C)C(C(=O)[O-])C1 | 1483.6 | Standard non polar | 33892256 | 4-Oxoproline,2TMS,isomer #1 | C[Si](C)(C)OC1=CN([Si](C)(C)C)C(C(=O)[O-])C1 | 1788.1 | Standard polar | 33892256 | 4-Oxoproline,2TMS,isomer #2 | C[Si](C)(C)OC1=CC(C(=O)[O-])N([Si](C)(C)C)C1 | 1445.0 | Semi standard non polar | 33892256 | 4-Oxoproline,2TMS,isomer #2 | C[Si](C)(C)OC1=CC(C(=O)[O-])N([Si](C)(C)C)C1 | 1447.9 | Standard non polar | 33892256 | 4-Oxoproline,2TMS,isomer #2 | C[Si](C)(C)OC1=CC(C(=O)[O-])N([Si](C)(C)C)C1 | 1739.0 | Standard polar | 33892256 | 4-Oxoproline,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CNC(C(=O)[O-])C1 | 1688.5 | Semi standard non polar | 33892256 | 4-Oxoproline,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CNC(C(=O)[O-])C1 | 1613.7 | Standard non polar | 33892256 | 4-Oxoproline,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CNC(C(=O)[O-])C1 | 2397.5 | Standard polar | 33892256 | 4-Oxoproline,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC(C(=O)[O-])NC1 | 1580.7 | Semi standard non polar | 33892256 | 4-Oxoproline,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC(C(=O)[O-])NC1 | 1578.1 | Standard non polar | 33892256 | 4-Oxoproline,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC(C(=O)[O-])NC1 | 2264.8 | Standard polar | 33892256 | 4-Oxoproline,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1CC(=O)CC1C(=O)[O-] | 1585.2 | Semi standard non polar | 33892256 | 4-Oxoproline,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1CC(=O)CC1C(=O)[O-] | 1612.9 | Standard non polar | 33892256 | 4-Oxoproline,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1CC(=O)CC1C(=O)[O-] | 2014.9 | Standard polar | 33892256 | 4-Oxoproline,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CN([Si](C)(C)C(C)(C)C)C(C(=O)[O-])C1 | 1944.5 | Semi standard non polar | 33892256 | 4-Oxoproline,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CN([Si](C)(C)C(C)(C)C)C(C(=O)[O-])C1 | 1890.0 | Standard non polar | 33892256 | 4-Oxoproline,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CN([Si](C)(C)C(C)(C)C)C(C(=O)[O-])C1 | 2024.8 | Standard polar | 33892256 | 4-Oxoproline,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC(C(=O)[O-])N([Si](C)(C)C(C)(C)C)C1 | 1882.3 | Semi standard non polar | 33892256 | 4-Oxoproline,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC(C(=O)[O-])N([Si](C)(C)C(C)(C)C)C1 | 1855.7 | Standard non polar | 33892256 | 4-Oxoproline,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC(C(=O)[O-])N([Si](C)(C)C(C)(C)C)C1 | 1996.2 | Standard polar | 33892256 |
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