Record Information |
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Version | 1.0 |
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Created at | 2020-04-17 19:20:16 UTC |
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Updated at | 2020-11-18 16:39:32 UTC |
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CannabisDB ID | CDB005209 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Delphinidin 3-glucoside |
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Description | Delphinidin 3-glucoside, also known as myrtillin, belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position. Delphinidin 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Delphinidin 3-glucoside is found, on average, in the highest concentration within a few different foods, such as bilberries, blackcurrants, and summer grapes and in a lower concentration in common beans, lowbush blueberries, and red raspberries. Delphinidin 3-glucoside has also been detected, but not quantified in, several different foods, such as eggplants, fruits, rubus (blackberry, raspberry), sweet cherries, and black chokeberries. This could make delphinidin 3-glucoside a potential biomarker for the consumption of these foods. An anthocyanin cation consisting of delphinidin having a beta-D-glucosyl residue attached at the 3-hydroxy position. Delphinidin 3-glucoside 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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Delfinidin 3-O-beta-D-glucoside | ChEBI | Delphinidin 3-O-glucoside | ChEBI | Mirtillin | Kegg | Delphinidin 3-O-beta-D-glucoside | Kegg | Delfinidin 3-O-b-D-glucoside | Generator | Delfinidin 3-O-β-D-glucoside | Generator | Delphinidin 3-O-b-D-glucoside | Generator | Delphinidin 3-O-β-D-glucoside | Generator | Delphinidin 3-monoglucoside | HMDB | Delphinidin 3-O-beta-D-glucopyranoside | HMDB, MeSH | Delphinidol 3-glucoside | HMDB | Myrtillin | HMDB, MeSH | Myrtillin a | HMDB | Delphinidin 3-O-glucopyranoside | MeSH, HMDB | Delphinidin 3-O-beta-glucoside | MeSH, HMDB | Delphinidin-3-glucoside | MeSH, HMDB |
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Chemical Formula | C21H21O12 |
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Average Molecular Weight | 465.38 |
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Monoisotopic Molecular Weight | 465.1033 |
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IUPAC Name | 5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium |
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Traditional Name | 5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium |
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CAS Registry Number | 6906-38-3 |
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SMILES | OC[C@H]1O[C@@H](OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C21H20O12/c22-6-15-17(28)18(29)19(30)21(33-15)32-14-5-9-10(24)3-8(23)4-13(9)31-20(14)7-1-11(25)16(27)12(26)2-7/h1-5,15,17-19,21-22,28-30H,6H2,(H4-,23,24,25,26,27)/p+1/t15-,17-,18+,19-,21-/m1/s1 |
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InChI Key | XENHPQQLDPAYIJ-PEVLUNPASA-O |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | Flavonoid glycosides |
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Direct Parent | Anthocyanidin-3-O-glycosides |
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Alternative Parents | |
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Substituents | - Oligosaccharide
- Anthocyanidin-3-o-glycoside
- Flavonoid-3-o-glycoside
- Hydroxyflavonoid
- 3'-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Anthocyanidin
- O-glycosyl compound
- Glycosyl compound
- 1-benzopyran
- Benzopyran
- Catechol
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- 1-hydroxy-4-unsubstituted benzenoid
- Monocyclic benzene moiety
- Benzenoid
- Oxane
- Heteroaromatic compound
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Polyol
- Acetal
- Primary alcohol
- Hydrocarbon derivative
- Organic oxygen compound
- Alcohol
- Organooxygen compound
- Organic cation
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Biological role: |
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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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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Delphinidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0feb-9602600000-45aed3fc2911f95c79eb | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-014i-5510009000-d60ac3b75f44a32e605b | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, TMS_3_54, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, TMS_4_71, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, TMS_4_81, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, TMS_4_87, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, TMS_4_88, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, TMS_5_76, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, TMS_5_82, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, TMS_5_83, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, TMS_5_87, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, TMS_5_88, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, TMS_5_91, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, TMS_6_58, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, TMS_6_59, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, TMS_6_62, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, TMS_6_63, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Delphinidin 3-glucoside, "Delphinidin 3-glucoside,3TMS,#54" TMS, 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 - LC-ESI-QTOF , negative | splash10-0w29-0139400000-820d95dd9b931186bf3c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0009100000-900e146ee03a33c5e31c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-001i-0091300000-9658b19c1d3c3ad88775 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0100900000-78712e7fc63bf2f6c41c | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dj-1300900000-174d36b448e52a2ab4a1 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0002-7902100000-1c91ff38e96e02e42e96 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-2300900000-0ea3c4becf795cde3fa2 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-6800900000-cf4c9c44468a09663848 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0596-9300000000-05d37d94d7cc9ad734d7 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0aos-0006900000-ff93644803a0dd8e09fa | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-0039400000-bcb4b7e5729a0597c0af | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0k9i-5398200000-c60c5f9ebfd4dff713d0 | 2021-09-22 | View Spectrum |
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