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[[email protected]@]22[[email protected]]1CC(=O)[[email protected]]1(C)[[email protected]@H]2CC[[email protected]@]2(C)[[email protected]@H](OC(=O)[[email protected]]3O[[email protected]@]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
Taxonomy
- Family
- Terpenoids
- Class
- Triterpenoids
- Sub-class
- Limonoids
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
| 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 |
Metabolism
No metabolism information available