Record Information |
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Version | 1.0 |
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Created at | 2022-09-03 14:56:46 UTC |
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Updated at | 2022-09-03 14:56:47 UTC |
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NP-MRD ID | NP0177149 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid |
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Description | Ala-Leu-Leu-His, also known as a-L-L-H or ALLH, 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-Leu-Leu-His 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)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid is found in Trypanosoma brucei. It was first documented in 2022 (PMID: 36057450). Based on a literature review a significant number of articles have been published on Ala-Leu-Leu-His (PMID: 36057449) (PMID: 36057448) (PMID: 36057447) (PMID: 36057446) (PMID: 36057441) (PMID: 36057445). |
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Structure | CC(C)C[C@H](N=C(O)[C@H](C)N)C(O)=N[C@@H](CC(C)C)C(O)=N[C@@H](CC1=CN=CN1)C(O)=O InChI=1S/C21H36N6O5/c1-11(2)6-15(25-18(28)13(5)22)19(29)26-16(7-12(3)4)20(30)27-17(21(31)32)8-14-9-23-10-24-14/h9-13,15-17H,6-8,22H2,1-5H3,(H,23,24)(H,25,28)(H,26,29)(H,27,30)(H,31,32)/t13-,15-,16-,17-/m0/s1 |
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Synonyms | Value | Source |
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a-L-L-H | ChEBI | ALLH | ChEBI | L-Ala-L-leu-L-leu-L-his | ChEBI |
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Chemical Formula | C21H36N6O5 |
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Average Mass | 452.5560 Da |
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Monoisotopic Mass | 452.27472 Da |
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IUPAC Name | (2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(1H-imidazol-5-yl)propanoic acid |
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Traditional Name | (2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3H-imidazol-4-yl)propanoic acid |
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CAS Registry Number | Not Available |
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SMILES | CC(C)C[C@H](N=C(O)[C@H](C)N)C(O)=N[C@@H](CC(C)C)C(O)=N[C@@H](CC1=CN=CN1)C(O)=O |
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InChI Identifier | InChI=1S/C21H36N6O5/c1-11(2)6-15(25-18(28)13(5)22)19(29)26-16(7-12(3)4)20(30)27-17(21(31)32)8-14-9-23-10-24-14/h9-13,15-17H,6-8,22H2,1-5H3,(H,23,24)(H,25,28)(H,26,29)(H,27,30)(H,31,32)/t13-,15-,16-,17-/m0/s1 |
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InChI Key | RGDKRCPIFODMHK-HJWJTTGWSA-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
- Histidine or derivatives
- Leucine or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- N-acyl-l-alpha-amino acid
- Alpha-amino acid amide
- Alanine or derivatives
- N-substituted-alpha-amino acid
- Alpha-amino acid or derivatives
- Imidazolyl carboxylic acid derivative
- N-acyl-amine
- Fatty amide
- Fatty acyl
- Imidazole
- Azole
- Heteroaromatic compound
- Secondary carboxylic acid amide
- Carboxamide group
- Amino acid
- Amino acid or derivatives
- Organoheterocyclic compound
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Azacycle
- Organic nitrogen compound
- Primary aliphatic amine
- Organonitrogen compound
- Organooxygen compound
- Primary amine
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Amine
- Organopnictogen compound
- Organic oxygen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic 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 | - Micalizzi E, Vaudano AE, Ballerini A, Talami F, Giovannini G, Turchi G, Cioclu MC, Giunta L, Meletti S: Ictal Apnea: a prospective monocentric study in patients with epilepsy. Eur J Neurol. 2022 Sep 3. doi: 10.1111/ene.15547. [PubMed:36057450 ]
- Jiang S, Guo P, Heo HY, Zhang Y, Wu J, Jin Y, Laterra J, Eberhart CG, Lim M, Blakeley JO: Radiomics analysis of amide proton transfer-weighted and structural MR images for treatment response assessment in malignant gliomas. NMR Biomed. 2022 Sep 3:e4824. doi: 10.1002/nbm.4824. [PubMed:36057449 ]
- Agarwal K, Saikia P, Podder I: Metabolic syndrome and Dyslipidemia in xanthelasma palpebrarum and associated risk-factors- a case-control study. J Cosmet Dermatol. 2022 Sep 3. doi: 10.1111/jocd.15353. [PubMed:36057448 ]
- Lebel V, Argiropoulos N, Robins S, Charbonneau L, Feeley N: Family-centred care and breastfeeding self-efficacy determined how ready mothers were for their infants to be discharged from a neonatal intensive care unit. Acta Paediatr. 2022 Sep 3. doi: 10.1111/apa.16538. [PubMed:36057447 ]
- Park JI, Kim SJ, Kim YJ, Lee SJ: Protective role of Caesalpinia sappan extract and its main component brazilin against blue light-induced damage in human fibroblasts. J Cosmet Dermatol. 2022 Sep 3. doi: 10.1111/jocd.15354. [PubMed:36057446 ]
- Ortiz G, Bastidas A, Garay-Fernandez M, Lara A, Benavides M, Rocha E, Buitrago A, Diaz G, Ordonez J, Reyes LF: Correlation and validity of imputed PaO2/FiO2 and SpO2/FiO2 in patients with invasive mechanical ventilation at 2600m above sea level. Med Intensiva (Engl Ed). 2022 Sep;46(9):501-507. doi: 10.1016/j.medine.2021.05.010. [PubMed:36057441 ]
- Laccourreye O: Dog days.... Eur Ann Otorhinolaryngol Head Neck Dis. 2022 Aug;139(4):171-172. doi: 10.1016/j.anorl.2022.08.003. [PubMed:36057445 ]
- Prissel MA, Solomon M: RE: Fellowships in Podiatric Medicine. J Foot Ankle Surg. 2022 Sep-Oct;61(5):1137. doi: 10.1053/j.jfas.2021.03.013. [PubMed:36057444 ]
- Ishikawa T, Inoue S, Kawaguchi M: A pediatric case of severe systemic pneumatosis during airway pressure release ventilation. Med Intensiva (Engl Ed). 2022 Sep;46(9):544-545. doi: 10.1016/j.medine.2020.03.007. [PubMed:36057443 ]
- Isidoro Duarte T, Amaral M, Pires C, Casimiro J, Germano N: Hemodynamic monitoring for liver transplantation: Agreement between invasive and non-invasive devices? Med Intensiva (Engl Ed). 2022 Sep;46(9):527-529. doi: 10.1016/j.medine.2021.06.006. [PubMed:36057442 ]
- LOTUS database [Link]
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