| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-02 02:07:18 UTC |
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| Updated at | 2022-09-02 02:07:18 UTC |
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| NP-MRD ID | NP0146680 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (2s)-1-(2-{[(2s)-2-amino-1-hydroxypropylidene]amino}acetyl)pyrrolidine-2-carboxylic acid |
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| Description | Ala-Gly-Pro, also known as a-g-p or L-ala-gly-L-pro, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Ala-Gly-Pro is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2s)-1-(2-{[(2s)-2-amino-1-hydroxypropylidene]amino}acetyl)pyrrolidine-2-carboxylic acid is found in Trypanosoma brucei. (2s)-1-(2-{[(2s)-2-amino-1-hydroxypropylidene]amino}acetyl)pyrrolidine-2-carboxylic acid was first documented in 2020 (PMID: 33071314). Based on a literature review a small amount of articles have been published on Ala-Gly-Pro (PMID: 35662307) (PMID: 33825882) (PMID: 33822356) (PMID: 33496711). |
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| Structure | C[C@H](N)C(O)=NCC(=O)N1CCC[C@H]1C(O)=O InChI=1S/C10H17N3O4/c1-6(11)9(15)12-5-8(14)13-4-2-3-7(13)10(16)17/h6-7H,2-5,11H2,1H3,(H,12,15)(H,16,17)/t6-,7-/m0/s1 |
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| Synonyms | | Value | Source |
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| a-g-p | ChEBI | | AGP | ChEBI | | L-Ala-gly-L-pro | ChEBI |
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| Chemical Formula | C10H17N3O4 |
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| Average Mass | 243.2630 Da |
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| Monoisotopic Mass | 243.12191 Da |
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| IUPAC Name | (2S)-1-(2-{[(2S)-2-amino-1-hydroxypropylidene]amino}acetyl)pyrrolidine-2-carboxylic acid |
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| Traditional Name | (2S)-1-(2-{[(2S)-2-amino-1-hydroxypropylidene]amino}acetyl)pyrrolidine-2-carboxylic acid |
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| CAS Registry Number | Not Available |
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| SMILES | C[C@H](N)C(O)=NCC(=O)N1CCC[C@H]1C(O)=O |
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| InChI Identifier | InChI=1S/C10H17N3O4/c1-6(11)9(15)12-5-8(14)13-4-2-3-7(13)10(16)17/h6-7H,2-5,11H2,1H3,(H,12,15)(H,16,17)/t6-,7-/m0/s1 |
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| InChI Key | MQIGTEQXYCRLGK-BQBZGAKWSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. |
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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 | Oligopeptides |
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| Alternative Parents | |
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| Substituents | - Alpha-oligopeptide
- N-acyl-alpha amino acid or derivatives
- Proline or derivatives
- N-acyl-alpha-amino acid
- N-acyl-l-alpha-amino acid
- Alpha-amino acid amide
- Alanine or derivatives
- Alpha-amino acid or derivatives
- N-acylpyrrolidine
- Pyrrolidine carboxylic acid
- Pyrrolidine carboxylic acid or derivatives
- Pyrrolidine
- Tertiary carboxylic acid amide
- Carboxamide group
- Secondary carboxylic acid amide
- Amino acid or derivatives
- Carboxylic acid salt
- Amino acid
- Monocarboxylic acid or derivatives
- Azacycle
- Carboxylic acid
- Organoheterocyclic compound
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Primary amine
- Organic zwitterion
- Primary aliphatic amine
- Organic salt
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organopnictogen compound
- Amine
- Organic oxygen compound
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| 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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| General References | - Sun L, Li M, Zhang S, Bao Z, Lin S: Mechanism of Ser-Ala-Gly-Pro-Ala-Phe treatment with a pulsed electric field to improve ethanol-induced gastric mucosa injury in mice. Food Funct. 2022 Jun 20;13(12):6716-6725. doi: 10.1039/d2fo00567k. [PubMed:35662307 ]
- Choudhury D, Biswas S: Structure-guided protein engineering of human cathepsin L for efficient collagenolytic activity. Protein Eng Des Sel. 2021 Feb 15;34:gzab005. doi: 10.1093/protein/gzab005. [PubMed:33825882 ]
- Xie Z, Wang X, Yu S, He M, Yu S, Xiao H, Song Y: Antioxidant and functional properties of cowhide collagen peptides. J Food Sci. 2021 May;86(5):1802-1818. doi: 10.1111/1750-3841.15666. Epub 2021 Apr 6. [PubMed:33822356 ]
- Shi J, Zhou X, Zhao Y, Tang X, Feng L, Wang B, Chen J: The three-spot seahorse-derived peptide PAGPRGPA attenuates ethanol-induced oxidative stress in LO2 cells through MAPKs, the Keap1/Nrf2 signalling pathway and amino acid metabolism. Food Funct. 2021 Mar 1;12(4):1672-1687. doi: 10.1039/d0fo02457k. [PubMed:33496711 ]
- Shi J, Su RQ, Zhang WT, Chen J: Purification and the secondary structure of a novel angiotensin I-converting enzyme (ACE) inhibitory peptide from the alcalase hydrolysate of seahorse protein. J Food Sci Technol. 2020 Nov;57(11):3927-3934. doi: 10.1007/s13197-020-04427-0. Epub 2020 Apr 15. [PubMed:33071314 ]
- LOTUS database [Link]
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