Compound Summary
Compound Information
Limonin
Compound Name: | Limonin |
Compound CID: | 179651 |
Synonyms: | Limonin 1180-71-8 Dictamnolactone Obaculactone Citrolimonin More... |
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[11.9.0.02,7.02,10.014,16.014,20]docosane-5,12,17-trione |
InChI: | 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 |
InChIKey: | KBDSLGBFQAGHBE-MSGMIQHVSA-N |
Canonical Smiles: | CC1(C2CC(=O)C3(C(C24COC(=O)CC4O1)CCC5(C36C(O6)C(=O)OC5C7=COC=C7)C)C)C |
Isomeric Smiles: | C[C@@]12CC[C@H]3[C@]([C@@]14[C@H](O4)C(=O)O[C@H]2C5=COC=C5)(C(=O)C[C@@H]6[C@@]37COC(=O)C[C@@H]7OC6(C)C)C |
Molecular Weight: | 470.5 |
Molecular Formula: | C26H30O8 |
Compound Structure
2D Structure:
3D Structure:
Computed Properties
Limonin
Molecular Weight: | 470.5 |
Molecular Formula: | C26H30O8 |
Hydrogen Bond Donor Count: | 0 |
Hydrogen Bond Acceptor Count: | 8 |
Rotatable Bond Count: | 1 |
Heavy Atom Count: | 34 |
Complexity: | 1010 |
Synonyms
Limonin
| Limonin | Limonin |
|---|---|
Limonin |
1180-71-8 |
Dictamnolactone |
Obaculactone |
Citrolimonin |
Evodin |
Limonine |
Limoni |
7,16-Dioxo-7,16-dideoxylimondiol |
Limonoic acid, di-delta-lactone |
Evodia fruit |
UNII-L0F260866S |
NSC 36508 |
limonoic acid 3,19:16,17-dilactone |
Limonoate D-ring-lactone |
(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-1H,3H-oxireno2,3-dpyrano4,3:3,3aisobenzofuro5,4-fisochromene-3,8,10(6H,9aH)-trione |
CHEBI:16226 |
MFCD00075922 |
L0F260866S |
Limonoic acid 3,19:16,17 dilactone |
DSSTox_CID_25985 |
DSSTox_RID_81273 |
DSSTox_GSID_45985 |
(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydrooxireno2,3-dpyrano4,3:3,3aisobenzofuro5,4-fisochromene-3,8,10(1H,6H,8aH)-trione |
Limone |
(4aS,6aR,8aR,8bR,9aS,12R,12aS,14aR,14bR)-12-(3-furyl)-6,6,8a,12a-tetramethyldecahydro-3H-oxirenodpyrano4,3:3,3a2benzofuro5,4-fisochromene-3,8,10(6H,9aH)-trione |
CAS-1180-71-8 |
3-furyl(tetramethyl)?trione |
Linonin |
NSC36508 |
CCRIS 4047 |
NCGC00095714-01 |
AI3-37932 |
Spectrum2_001728 |
Spectrum3_001012 |
Spectrum4_001140 |
Spectrum5_000935 |
Limonin, analytical standard |
BSPBio_002763 |
KBioGR_001659 |
Limonoic acid di-del.-lactone |
SCHEMBL320315 |
SPECTRUM1800018 |
SPBio_001776 |
CHEMBL517449 |
DTXSID8045985 |
ACon1_001996 |
KBio3_001983 |
Limonoic acid di-.delta.-lactone |
11H,13H-Oxireno(d)pyrano(4,3:3,3a)isobenzofuro(5,4-f)(2)benzopyran-4,6,13(2H,5aH)-trione, 8-(3-furanyl)decahydro-2,2,4a,8a-tetramethyl-, (2aR,4aR,4bR,5aS,8S,8aS,10aR,10bR,14aS)- |
ZINC4096134 |
Tox21_111513 |
BDBM50418089 |
CCG-38796 |
AKOS015965307 |
Tox21_111513_1 |
AC-8045 |
CS-1237 |
SDCCGMLS-0066837.P001 |
NCGC00178483-01 |
NCGC00178483-02 |
NCGC00178483-04 |
NCGC00178483-05 |
NCGC00178483-14 |
NCGC00263659-01 |
11H,13H-Oxireno(d)pyrano(4,3:3,3a)isobenzofuro(5,4-f)(2)benzopyran-4,6,13(2H,5aH)-trione, 8-(3-furyl)decahydro-2,2,4a,8a-tetramethyl- |
AS-15249 |
HY-17411 |
O622 |
AB0016554 |
L0258 |
Limonin, from citrus seeds, >90% (HPLC) |
N1349 |
S2319 |
C03514 |
180L718 |
A854522 |
Q-100083 |
Q2398745 |
BRD-K05906022-001-03-6 |
BRD-K05906022-001-05-1 |
Limone; Citrolimonin; Evodine; Dictamnolactone; Obaculactone |
(1R,2R,7S,10R,13R,14R,16S,19S,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo11.9.0.02,7.02,10.014,16.014,20docosane-5,12,17-trione |
(4aS,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-1H,3H-oxireno2,3-dpyrano4,3:3,3aisobenzofuro5,4-fisochromene-3,8,10(6H,9aH)-trione" |
(4aS,6aR,8aR,8bR,9aS,12R,12aS,14aR,14bR)-12-(furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-3H-oxirenodpyrano4,3:3,3a2benzofuro5,4-fisochromene-3,8,10(6H,9aH)-trione" |
11H,13H-Oxireno(d)pyrano(4,3:3,3a)isobenzofuro(5,4-f)(2)benzopyran-4,6,13(2H,5aH)-trione, 8-(3-furanyl)decahydro-2,2,4a,8a-tetramethyl-, (2aR-(2aalpha,4abeta,4bR,5aalpha,8alpha,8aalpha,10aalpha,10bR*,14aalpha))- |
1809582-56-6 |
rel-(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydrooxireno2,3-dpyrano4,3:3,3aisobenzofuro5,4-fisochromene-3,8,10(1H,6H,8aH)-trione" |
Experimental Data
Limonin
| Species | Dosage | Unit | CG Lifespan(AVG/MED days) | TG Lifespan(AVG/MED days) | Lifespan Change(AVG/MED%) | CG Lifespan(MAX days) | TG Lifespan(MAX days) | Lifespan Change(MAX%) | Significant | Strain | Gender | PubMed | Active Label |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Caenorhabditis elegans | 100 | umol/L | 15.99 | 15.87 | -0.7926 | NS | N2 | 33008901 | Inactive | ||||
| Caenorhabditis elegans | 10 | umol/L | 16.18 | 15.63 | -3.41 | NS | N2 | 33008901 | Inactive | ||||
| Drosophila melanogaster | 20 | umol/L | 47.99 | 46.74 | -2.61 | NS | FEMALES | 33008901 | Inactive | ||||
| Drosophila melanogaster | 200 | umol/L | 42.22 | 40.72 | -3.55 | NS | MALES | 33008901 | Inactive |
Experimental Data Visualization
Limonin
Statistics Data
Limonin
| Species | Lifespan Change(AVG/MED%) | Lifespan Change(MAX%) | Count Reference | Count Data point |
|---|---|---|---|---|
| Caenorhabditis elegans | -0.7926 | 1 | 2 | |
| Drosophila melanogaster | -2.61 | 1 | 2 |
Statistics Data Visualization
Limonin
