| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-12 15:12:26 UTC |
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| Updated at | 2022-05-12 15:12:26 UTC |
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| NP-MRD ID | NP0136355 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Arginylphenylalanine |
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| Description | Arginylphenylalanine, also known as RF or L-arg-L-phe, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Arginylphenylalanine is a very strong basic compound (based on its pKa). Arginylphenylalanine was first documented in 1983 (PMID: 6137771). It is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 22945436). |
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| Structure | N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O InChI=1S/C15H23N5O3/c16-11(7-4-8-19-15(17)18)13(21)20-12(14(22)23)9-10-5-2-1-3-6-10/h1-3,5-6,11-12H,4,7-9,16H2,(H,20,21)(H,22,23)(H4,17,18,19)/t11-,12-/m0/s1 |
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| Synonyms | | Value | Source |
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| Arginyl-phenylalanine | ChEBI | | L-Arg-L-phe | ChEBI | | RF | ChEBI | | Arg-phe | HMDB | | Arginine phenylalanine dipeptide | HMDB | | Arginine-phenylalanine dipeptide | HMDB | | L-Arginyl-L-phenylalanine | HMDB | | N-Arginylphenylalanine | HMDB | | N-L-Arginyl-3-phenylalanine | HMDB | | N-L-Arginyl-L-phenylalanine | HMDB | | R-F Dipeptide | HMDB | | RF Dipeptide | HMDB | | Arginylphenylalanine | ChEBI |
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| Chemical Formula | C15H23N5O3 |
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| Average Mass | 321.3810 Da |
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| Monoisotopic Mass | 321.18009 Da |
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| IUPAC Name | (2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-phenylpropanoic acid |
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| Traditional Name | (2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-phenylpropanoic acid |
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| CAS Registry Number | Not Available |
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| SMILES | N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O |
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| InChI Identifier | InChI=1S/C15H23N5O3/c16-11(7-4-8-19-15(17)18)13(21)20-12(14(22)23)9-10-5-2-1-3-6-10/h1-3,5-6,11-12H,4,7-9,16H2,(H,20,21)(H,22,23)(H4,17,18,19)/t11-,12-/m0/s1 |
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| InChI Key | PQBHGSGQZSOLIR-RYUDHWBXSA-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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 | Not Available |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. |
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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 | Dipeptides |
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| Alternative Parents | |
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| Substituents | - Alpha-dipeptide
- Phenylalanine or derivatives
- N-acyl-alpha amino acid or derivatives
- N-acyl-alpha-amino acid
- N-acyl-l-alpha-amino acid
- Alpha-amino acid amide
- 3-phenylpropanoic-acid
- Alpha-amino acid or derivatives
- Amphetamine or derivatives
- Monocyclic benzene moiety
- N-acyl-amine
- Benzenoid
- Fatty amide
- Fatty acyl
- Guanidine
- Amino acid or derivatives
- Amino acid
- Carboxamide group
- Secondary carboxylic acid amide
- Organic 1,3-dipolar compound
- Carboxylic acid
- Propargyl-type 1,3-dipolar organic compound
- Carboximidamide
- Monocarboxylic acid or derivatives
- Organopnictogen compound
- Amine
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Hydrocarbon derivative
- Primary aliphatic amine
- Organic oxide
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic 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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