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

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

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 IDSourceDescriptionView
TY000204MassBankLC-ESI-ITTOF Spectrum - -, unspecifiedView Spectra

Food Sources

Metabolism

No metabolism information available

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