| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:12:04 UTC |
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| Update date | 2019-11-26 03:12:15 UTC |
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| Primary ID | FDB015814 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Ginkgolide C |
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| Description | ginkgolide-C belongs to the class of organic compounds known as ginkgolides and bilobalides. These are diterpene lactones with a structure based either on the gingkolide or the bilobalide skeleton. The ginkgolide skeleton is a very rigid structure consisting of hexacyclic C20 trilactone. The cis-fused F/A/D/C ring junction forms an empty semi-ball hole, the D ring contains a cage form tetrahydrofuran ring which occupies the center of the empty hole, and the oxygen atoms of the D,C and F ring and 10-hydroxyl group consist of an analogous crown ether structure. ginkgolide-C is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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| CAS Number | 15291-76-6 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C20H24O11 |
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| IUPAC name | (1R,3R,6R,7S,8S,9R,10S,11R,12R,13S,16S,17R)-8-tert-butyl-6,9,12,17-tetrahydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0^{1,11}.0^{3,7}.0^{7,11}.0^{13,17}]nonadecane-5,15,18-trione |
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| InChI Identifier | InChI=1S/C20H24O11/c1-5-12(24)28-11-8(22)18-10-6(21)7(16(2,3)4)17(18)9(23)13(25)30-15(17)31-20(18,14(26)29-10)19(5,11)27/h5-11,15,21-23,27H,1-4H3/t5-,6-,7+,8+,9+,10-,11+,15+,17+,18-,19-,20-/m1/s1 |
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| InChI Key | AMOGMTLMADGEOQ-DTDWCABLSA-N |
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| Isomeric SMILES | C[C@@H]1C(=O)O[C@H]2[C@H](O)[C@]34[C@@H]5OC(=O)[C@]3(O[C@@H]3OC(=O)[C@H](O)[C@]43[C@@H]([C@H]5O)C(C)(C)C)[C@@]12O |
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| Average Molecular Weight | 440.398 |
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| Monoisotopic Molecular Weight | 440.13186161 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as ginkgolides and bilobalides. These are diterpene lactones with a structure based either on the gingkolide or the bilobalide skeleton. The ginkgolide skeleton is a very rigid structure consisting of hexacyclic C20 trilactone. The cis-fused F/A/D/C ring junction forms an empty semi-ball hole, the D ring contains a cage form tetrahydrofuran ring which occupies the center of the empty hole, and the oxygen atoms of the D,C and F ring and 10-hydroxyl group consist of an analogous crown ether structure. |
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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 lactones |
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| Direct Parent | Ginkgolides and bilobalides |
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| Alternative Parents | |
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| Substituents | - Ginkgolide-skeleton
- Diterpenoid
- Tricarboxylic acid or derivatives
- Furofuran
- Gamma butyrolactone
- Cyclic alcohol
- Tetrahydrofuran
- Tertiary alcohol
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Acetal
- Carboxylic acid derivative
- Polyol
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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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 | Not Available |
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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 | splash10-0006-0002900000-0ce0e1488c887f67daac | 2017-07-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0596-1009600000-6529acd5f9c76740cc94 | 2017-07-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05i0-6009400000-60c6d5cfdb45c0601d02 | 2017-07-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0004900000-6a946e2c3c15f0d03c0e | 2017-07-26 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-007a-1009600000-bc52522e05d5e253ba12 | 2017-07-26 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0002-1019000000-9a58ed62507a9b233bd9 | 2017-07-26 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 141541 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | C07603 |
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| Pubchem Compound ID | 161120 |
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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 | HMDB36860 |
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| CRC / DFC (Dictionary of Food Compounds) ID | KJN05-G:KJN05-G |
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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 | C00035831 |
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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 | |
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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 | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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