Limonin
precursor
Showing entry for Limonin
Identification
- PhytoHub ID
- PHUB000172
- Name
- Limonin
- Systematic Name
- Not Available
- Synonyms
- Citrolimonin
- Dictamnolactone
- Evodin
- Obaculactone
- CAS Number
- Not Available
- Average Mass
- 470.518
- Monoisotopic Mass
- 470.194067926
- Chemical Formula
- C26H30O8
- IUPAC Name
- (1R,2R,7S,10R,13R,14R,16S,19S,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0^{2,7}.0^{2,10}.0^{14,16}.0^{14,20}]docosane-5,12,17-trione
- InChI Key
- KBDSLGBFQAGHBE-MSGMIQHVSA-N
- InChI Identifier
InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1
- SMILES
CC1(C)O[[email protected]]2CC(=O)OC[C@@]22[[email protected]]1CC(=O)[C@]1(C)[C@@H]2CC[C@@]2(C)[C@@H](OC(=O)[[email protected]]3O[C@@]123)C1=COC=C1
- Structure
Structure for Limonin
Calculated Properties
- Solubility (ALOGPS)
- 7.99e-02 g/l
- LogS (ALOGPS)
- -3.77
- LogP (ALOGPS)
- 3.47
- Hydrogen Acceptors
- 5
- Hydrogen Donors
- 0
- Rotatable Bond Count
- 1
- Polar Surface Area
- 104.57000000000001
- Refractivity
- 114.7192
- Polarizability
- 47.913676024162086
- Formal Charge
- 0
- Physiological Charge
- 0
- pKa (strongest basic)
- -2.8525572165882376
- pKa (strongest acidic)
- 19.475883044026496
- Number of Rings
- 7
- Rule of Five
- Yes
- Bioavailability
- Yes
- Ghose Filter
- Yes
- Veber's Rule
- No
- MDDR-like Rule
- No
External Links
- ChEBI
- 16226
- PubChem
- 179651
- Chemistry Dashboard
- DTXSID8045985
- MetaboLights
- MTBLC16226
- FooDB (Compounds)
- FDB005049
- PeakForestCompound
- 000159
Taxonomy as Food Phytochemical
- Family
- Terpenoids
- Class
- Triterpenoids
- Sub-class
- Limonoids
Taxonomy as Metabolite
- Metabolite Family
- Terpenoid metabolites
- Metabolite Class
- Triterpenoid metabolites
- Metabolite Sub-class
- Limonoids (parent, host and microbial metabolites)
Taxonomy of its Food Phytochemical Precursor(s)
| Food Phytochemical | Family | Class | Sub-class | |
|---|---|---|---|---|
| Limonin Glucoside | Terpenoids | Triterpenoids | Limonoids | Show Food Phytochemical |
Classyfire Taxonomy
- Kingdom Name
- Organic compounds
- Class
- Prenol lipids
- Super-class
- Lipids and lipid-like molecules
- Sub-class
- Triterpenoids
- Direct Parent Name
- Limonoids
- Alternative Parent Names
- ["1,4-dioxepanes", "11-oxosteroids", "Carboxylic acid esters", "Delta valerolactones", "Dialkyl ethers", "Dicarboxylic acids and derivatives", "Epoxides", "Furans", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Ketones", "Naphthalenes", "Naphthopyrans", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Pyrans", "Steroid lactones", "Tetrahydrofurans"]
- External Descriptor Annotations
- ["Limonoids", "epoxide", "furans", "hexacyclic triterpenoid", "lactone", "limonoid", "organic heterohexacyclic compound"]
- Substituent Names
- ["1,4-dioxepane", "11-oxosteroid", "2-oxosteroid", "Aromatic heteropolycyclic compound", "Carbonyl group", "Carboxylic acid derivative", "Carboxylic acid ester", "Delta valerolactone", "Delta_valerolactone", "Dialkyl ether", "Dicarboxylic acid or derivatives", "Dioxepane", "Ether", "Furan", "Heteroaromatic compound", "Hydrocarbon derivative", "Ketone", "Lactone", "Limonoid skeleton", "Naphthalene", "Naphthopyran", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "Oxirane", "Oxosteroid", "Pyran", "Steroid", "Steroid lactone", "Tetrahydrofuran"]
Spectra from Online Resources
| Record ID | Source | Description | View |
|---|---|---|---|
| TY000204 | MassBank | LC-ESI-ITTOF Spectrum - -, unspecified | View Spectra |
Food Sources
| Name | Group | |||
|---|---|---|---|---|
| Grapefruit | Fruit, Citrus | Publications | Show | |
| Sour orange | Fruit, Citrus | Publications | Show | |
| Sweet orange | Fruit, Citrus | Publications | Show |
Food Sources of its Food Phytochemical(s)
| Food Phytochemical | Food Source | Food Source Group | |||
|---|---|---|---|---|---|
| Limonin Glucoside | Citrus fruits and Juices | Fruit, Citrus | Publications | Show | |
| Limonin Glucoside | Grapefruit | Fruit, Citrus | Publications | Show | |
| Limonin Glucoside | Mandarin orange (Clementine, Tangerine) | Fruit, Citrus | Publications | Show | |
| Limonin Glucoside | Sweet orange | Fruit, Citrus | Publications | Show |
Role as Biomarker of intake
No roles as Biomarker of intake found
Metabolism
| Food Phytochemical | Metabolite | Species | Biofluids | Origin | TMax | CMax | Urinary Excretion | Formula | Monoisotopic mass | ||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Limonin Glucoside | Limonin | human | plasma | host metabolism | 5h-8h | <20 nmol/L | Not Available | C26H30O8 | 470.194067926 | Detailed Intervention Studies |
Inter-Individual Variations Metabolism
| Food Phytochemical | Metabolite | Effect | Value | |||
|---|---|---|---|---|---|---|
| Limonin Glucoside | Limonin | BMI | No effect | Publications | ||
| Limonin Glucoside | Limonin | Smoking | Not studied | |||
| Limonin Glucoside | Limonin | Ethnicity | Not studied | |||
| Limonin Glucoside | Limonin | Genotype | Not studied | |||
| Limonin Glucoside | Limonin | Microbiota | Not studied | |||
| Limonin Glucoside | Limonin | Sex | No effect | Publications | ||
| Limonin Glucoside | Limonin | Age | No effect | Publications | ||
| Limonin Glucoside | Limonin | Health-Status | Not studied |