Record Information |
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Version | 1.0 |
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Created at | 2020-04-17 18:36:31 UTC |
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Updated at | 2020-12-07 19:10:55 UTC |
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CannabisDB ID | CDB004785 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Tetrahydrobiopterin |
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Description | L-erythro-tetrahydrobiopterin, also known as 5,6,7,8-tetrahydrobiopterin or 6R-BH4, belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland. It is also essential in the conversion of phenylalanine to tyrosine by the enzyme phenylalanine-4-hydroxylase; the conversion of tyrosine to L-dopa by the enzyme tyrosine hydroxylase; and conversion of tryptophan to 5-hydroxytryptophan via tryptophan hydroxylase. In the hydroxylation process, the co-enzyme loses two electrons and is regenerated in vivo in an NADH-dependent reaction. L-erythro-tetrahydrobiopterin is a drug which is used for the treatment of tetrahydrobiopterin (bh4) deficiency. Tetrahydrobiopterin is also a natural co-factor for nitrate oxide synthase. L-erythro-tetrahydrobiopterin is a moderately basic compound (based on its pKa). L-erythro-tetrahydrobiopterin exists in all living organisms, ranging from bacteria to humans. L-phenylalanine and L-erythro-tetrahydrobiopterin can be converted into L-tyrosine and 4a-hydroxytetrahydrobiopterin; which is mediated by the enzyme phenylalanine-4-hydroxylase. Individuals with a deficiency in tetrahydrobiopterin are not able to efficiently convert phenylalanine to tyrosine. These genes make the enzymes that are critical for producing and recycling tetrahydrobiopterin. In humans, L-erythro-tetrahydrobiopterin is involved in the metabolic disorder called tyrosinemia type 3 (tyro3). As a co-factor for tyrosine hydroxylase, BH4 facilitates the conversion of tyrosine to L-dopa while as a co-factor for tryptophan hydroxylase, BH4 allows the conversion of tryptophan to 5-hydroxytryptophan, which is then converted to serotonin. Tetrahydrobiopterin (BH4) is used to convert several amino acids, including phenylalanine, to other essential molecules in the body including neurotransmitters. As a result, phenylalanine from the diet builds up in the bloodstream and other tissues and can damage nerve cells in the brain. Tetrahydrobiopterin is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | |
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Synonyms | Value | Source |
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(-)-(6R)-2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone | ChEBI | (6R)-L-Erythro-5,6,7,8-tetrahydrobiopterin | ChEBI | (6R)-L-Erythro-tetrahydrobiopterin | ChEBI | 2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinone | ChEBI | 5,6,7,8-Tetrahydrobiopterin | ChEBI | 6R-5,6,7,8-Tetrahydrobiopterin | ChEBI | 6R-BH4 | ChEBI | 6R-L-5,6,7,8-Tetrahydrobiopterin | ChEBI | R-THBP | ChEBI | Sapropterina | ChEBI | Sapropterinum | ChEBI | Tetrahydrobiopterin | ChEBI | 5,6,7,8-erythro-Tetrahydrobiopterin | MeSH, HMDB | 5,6,7,8-tetrahydro-L-Erythrobiopterin | MeSH, HMDB | 5,6,7,8-Tetrahydrobiopterin, (S-(r*,s*))-isomer | MeSH, HMDB | 5,6,7,8-Tetrahydrodictyopterin | MeSH, HMDB | 6R-L-erythro-5,6,7,8-Tetrahydrobiopterin | MeSH, HMDB | BPH4 | MeSH, HMDB | D-threo-Tetrahydrobiopterin | MeSH, HMDB | THBP | MeSH, HMDB | Kuvan | MeSH, HMDB | Phenylalanine hydroxylase cofactor | MeSH, HMDB | Sapropterin dihydrochloride | MeSH, HMDB | tetrahydro-6-Biopterin | MeSH, HMDB | 2',4',5'-Trihydroxybutyrophenone | MeSH | Sapropterin | MeSH | Trihydroxybutyrophenone | MeSH | 1-Butanone, 1-(2,4,5-trihydroxyphenyl) | MeSH | 2,4,5-Trihydroxybutyrophenone | MeSH | (6R)-5,6,7,8-Tetrahydro-L-biopterin | HMDB | (6R)-5,6,7,8-Tetrahydrobiopterin | HMDB | (6R)-Tetrahydrobiopterin | HMDB | 2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone | HMDB | 6R-Tetrahydro-L-biopterin | HMDB | 6beta-5,6,7,8-Tetrahydro-L-biopterin | HMDB | 6β-5,6,7,8-Tetrahydro-L-biopterin | HMDB | L-erythro-Tetrahydrobiopterin | HMDB | (6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-4(1H)-pteridinone | HMDB |
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Chemical Formula | C9H15N5O3 |
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Average Molecular Weight | 241.25 |
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Monoisotopic Molecular Weight | 241.1175 |
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IUPAC Name | (6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one |
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Traditional Name | tetrahydrobiopterin |
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CAS Registry Number | 62989-33-7 |
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SMILES | [H][C@@]1(CNC2=C(N1)C(=O)N=C(N)N2)[C@@H](O)[C@H](C)O |
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InChI Identifier | InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1 |
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InChI Key | FNKQXYHWGSIFBK-RPDRRWSUSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pteridines and derivatives |
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Sub Class | Pterins and derivatives |
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Direct Parent | Biopterins and derivatives |
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Alternative Parents | |
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Substituents | - Biopterin
- Aminopyrimidine
- Pyrimidone
- Secondary aliphatic/aromatic amine
- Pyrimidine
- 1,3-aminoalcohol
- Vinylogous amide
- Heteroaromatic compound
- Secondary alcohol
- 1,2-diol
- 1,2-aminoalcohol
- Secondary amine
- Azacycle
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Amine
- Alcohol
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Source: Biological location: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 250 - 255 °C (hydrochloride salt) | 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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GC-MS | Tetrahydrobiopterin, 6 TMS, GC-MS Spectrum | splash10-0zfr-2921300000-63bf6ee58b9df85919f6 | Spectrum | GC-MS | Tetrahydrobiopterin, non-derivatized, GC-MS Spectrum | splash10-0zfr-2921300000-63bf6ee58b9df85919f6 | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0005-9810000000-1bfd11724596b460cae9 | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-014i-6945000000-07faa91218e86d3bfe0d | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tetrahydrobiopterin, TMS_2_14, 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 - QTOF 4V, positive | splash10-0006-0290000000-cd4c8c11b8279075b00a | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QTOF 5V, positive | splash10-0006-0390000000-35dddce9e2df2a9ac198 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QTOF 7V, positive | splash10-0006-0590000000-cda875209a034e44cbe1 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QTOF 10V, positive | splash10-00kf-0980000000-53721c484501c528e7a8 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QTOF 15V, positive | splash10-014l-0930000000-533fabd35a8c5ca7830e | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QTOF 17V, positive | splash10-014i-0910000000-580c038db540047891c8 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QTOF 20V, positive | splash10-014i-0910000000-8d6b754dadadb6330906 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QTOF 3V, positive | splash10-0006-0090000000-f21b677255493f1f2d1f | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QTOF 23V, positive | splash10-014i-0900000000-5c1b60d0d7ea4dd4dbff | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QTOF 25V, positive | splash10-014i-1900000000-6f22457ab99b14bb653e | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QTOF 27V, positive | splash10-014i-1900000000-cd0410f4da61716c7f9e | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QTOF 30V, positive | splash10-014i-2900000000-d4f18a979b6d07e83a63 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 16V, positive | splash10-0002-0900000000-87174b78444828c3b52d | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 16V, positive | splash10-0a4i-0900000000-dc272a476d306f26c722 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 16V, positive | splash10-014i-0900000000-ae19513d01a0046ed2e8 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 16V, positive | splash10-004i-0900000000-d4a52489d35bde573bd0 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 16V, positive | splash10-0f79-0900000000-af02b0d9eb8f6577afb8 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 16V, positive | splash10-014i-0900000000-c2259602e8f1fd522fd0 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 4V, positive | splash10-0006-0090000000-c88ed5ea9e11715bc275 | 2020-07-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-006x-0090000000-e6b01d1139ccb3c6338d | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0gi3-0980000000-8963ef41f1138b05a813 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00xr-1900000000-bcfa359703563c696c0f | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0390000000-4810efa20f31adea3824 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-006y-1930000000-5b32feeb643e238bb159 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9400000000-a7dbebeb1df4ea110948 | 2015-09-15 | View Spectrum |
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NMR | Not Available |
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Pathways |
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Pathways | Name | SMPDB/Pathwhiz | KEGG | Pterine Biosynthesis | | | Catecholamine Biosynthesis | | | Dopa-responsive dystonia | | Not Available | Hyperphenylalaniemia due to guanosine triphosphate cyclohydrolase deficiency | | Not Available | Hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase deficiency (ptps) | | Not Available |
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Protein Targets |
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Enzymes | |
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Transporters | |
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Metal Bindings | |
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Receptors | |
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Transcriptional Factors | |
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Concentrations Data |
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| Not Available |
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External Links |
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HMDB ID | HMDB0059658 |
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DrugBank ID | DB00360 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 40270 |
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KEGG Compound ID | C00272 |
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BioCyc ID | CPD-14053 |
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BiGG ID | Not Available |
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Wikipedia Link | Sapropterin |
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METLIN ID | Not Available |
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PubChem Compound | 44257 |
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PDB ID | Not Available |
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ChEBI ID | 59560 |
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References |
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General References | Not Available |
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