Record Information |
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Version | 1.0 |
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Creation date | 2015-05-07 20:43:17 UTC |
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Update date | 2019-11-26 03:22:01 UTC |
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Primary ID | FDB030984 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | loganin |
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Description | Loganin, also known as loganoside, is a member of the class of compounds known as iridoid o-glycosides. Iridoid o-glycosides are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. Thus, loganin is considered to be an isoprenoid lipid molecule. Loganin is soluble (in water) and a very weakly acidic compound (based on its pKa). Loganin can be found in a number of food items such as groundcherry, annual wild rice, muscadine grape, and broad bean, which makes loganin a potential biomarker for the consumption of these food products. Loganin is one of the best-known of the iridoid glycosides.It is named for the Loganiaceae,having first been isolated from the seeds of a member of that plant family, namely those of Strychnos nux-vomica. It also occurs in Alstonia boonei (Apocynaceae), a medicinal tree of West Africa and in the medicinal/entheogenic shrub Desfontainia spinosa (Columelliaceae) native to Central America and South America . |
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CAS Number | 18524-94-2 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C17H26O10 |
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IUPAC name | methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate |
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InChI Identifier | InChI=1S/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9-,10+,11+,12+,13-,14+,16-,17-/m0/s1 |
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InChI Key | AMBQHHVBBHTQBF-UOUCRYGSSA-N |
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Isomeric SMILES | [H][C@]1(O)C[C@]2([H])C(=CO[C@@]([H])(O[C@]3([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]3([H])O)[C@]2([H])[C@@]1([H])C)C(=O)OC |
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Average Molecular Weight | 390.3823 |
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Monoisotopic Molecular Weight | 390.152597052 |
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Classification |
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Description | Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Terpene glycosides |
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Direct Parent | Iridoid O-glycosides |
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Alternative Parents | |
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Substituents | - Iridoid o-glycoside
- Hexose monosaccharide
- Glycosyl compound
- Iridoid-skeleton
- O-glycosyl compound
- Bicyclic monoterpenoid
- Monoterpenoid
- Monosaccharide
- Oxane
- Cyclic alcohol
- Vinylogous ester
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Methyl ester
- Carboxylic acid ester
- Secondary alcohol
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Oxacycle
- Acetal
- Carboxylic acid derivative
- Polyol
- Organooxygen compound
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Primary alcohol
- Carbonyl group
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | loganin, 5 TMS, GC-MS Spectrum | splash10-0159-0941000000-2488084a345bbbef3720 | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03fr-0698000000-996523546d898ac44ca2 | 2019-02-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-0952000000-bfd2e13cb45ce699bda8 | 2019-02-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0292-4921000000-77379174eb3eab062c89 | 2019-02-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0550-0479000000-48d9fe535515c2f903db | 2019-02-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0729-3976000000-f4f14d2c989937ff4de4 | 2019-02-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-4920000000-116f9827470c6ff06f0f | 2019-02-23 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | Not Available |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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