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Limonin
- Family: Plantae - Rutaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Limonoid
| Canonical Smiles | O=C1OC[C@]23[C@H](C1)OC([C@@H]2CC(=O)[C@@]1([C@@H]3CC[C@@]2([C@]31O[C@@H]3C(=O)O[C@H]2c1cocc1)C)C)(C)C |
|---|---|
| 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 |
| Formula | C26H30O8 |
| HBA | 8 |
| HBD | 0 |
| MW | 470.52 |
| Rotatable Bonds | 1 |
| TPSA | 104.57 |
| LogP | 3.14 |
| Number Rings | 7 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.73 |
| Exact Mass | 470.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Vepris glomerata | Rutaceae | Plantae | 2695416 |
| 2 | Vepris glomerata | Rutaceae | Plantae | 2695416 |
| 3 | Calodendrum capense | Rutaceae | Plantae | 68533 |
Showing of synonyms
Limonin
1180-71-8
Obaculactone
Citrolimonin
Evodin
Limonine
7,16-Dioxo-7,16-dideoxylimondiol
Limonoic acid, di-delta-lactone
Limonoic acid 3,19:16,17-dilactone
CCRIS 4047
UNII-L0F260866S
CHEBI:16226
Limonoic acid, di-.delta.-lactone
LIMONIN [MI]
NSC 36508
L0F260866S
AI3-37932
NSC-36508
(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
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-
(4aS,6aR,8aR,8bR,9aS,12R,12aS,14aR,14bR)-12-(3-furyl)-6,6,8a,12a-tetramethyldecahydro-3H-oxireno[d]pyrano[4',3':3,3a][2]benzofuro[5,4-f]isochromene-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,4aR,4bR,5aS,8S,8aS,10aR,10bR,14aS)-
Evodine?
Limone?
(4aS,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-1H,3H-oxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-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))-
Evodia fruit (JP15)
(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
(4aS,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-1H,3H-oxireno(2,3-d)pyrano(4',3':3,3a)isobenzofuro(5,4-f)isochromene-3,8,10(6H,9aH)-trione
(4aS,6aR,8aR,8bR,9aS,12R,12aS,14aR,14bR)-12-(3-furyl)-6,6,8a,12a-tetramethyldecahydro-3H-oxireno(d)pyrano(4',3':3,3a)(2)benzofuro(5,4-f)isochromene-3,8,10(6H,9aH)-trione
808-129-1
Kbdslgbfqaghbe-uhfffaoysa-n
Dictamnolactone
Limoni
Limonoic acid 3,19:16,17 dilactone
MFCD00075922
Limonoate D-ring-lactone
(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-1H,3H-oxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione
DTXSID8045985
(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydrooxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(1H,6H,8aH)-trione
DTXCID6025985
1809582-56-6
Rel-(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydrooxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(1H,6H,8aH)-trione
CAS-1180-71-8
Limonoic acid di-delta-lactone
3-furyl(tetramethyl)[?]trione
Linonin
NSC36508
NCGC00095714-01
Limonin (Standard)
Spectrum2_001728
Spectrum3_001012
Spectrum4_001140
Spectrum5_000935
Limonin, analytical standard
BSPBio_002763
KBioGR_001659
SCHEMBL320315
SPECTRUM1800018
SPBio_001776
CHEMBL517449
ACon1_001996
KBio3_001983
Limonoic acid di-.delta.-lactone
Tox21_111513
BDBM50418089
CCG-38796
HY-17411R
MSK157590
Di-delta-lactone limonoic acid
AKOS015965307
Tox21_111513_1
AC-8045
CS-1237
FL09973
SDCCGMLS-0066837.P001
NCGC00178483-01
NCGC00178483-02
NCGC00178483-04
NCGC00178483-05
NCGC00178483-14
NCGC00263659-01
AS-15249
HY-17411
1ST157590
L0258
Limonin, from citrus seeds, >90% (HPLC)
S2319
C03514
Q2398745
BRD-K05906022-001-03-6
BRD-K05906022-001-05-1
Limone
Evodine
- Kiplimo JJ, Koorbanally NA. (2012). Antibacterial activity of an epoxidised prenylated cinnamaldehdye derivative from Vepris glomerata. Phytochemistry Letters,2012,5(3),438-442. [View] [PubMed]
- Kiprop AK, Rajab MS, et al. (2005). Isolation and characterization of larvicidal components against mosquito larvae (Aedes aegypti Linn.) from Calodendrum capense Thunb. Bulletin of the Chemical Society of Ethiopia,2005,19(1),145-148. [View] [PubMed]
- Kiplimo JJ, Koorbanally NA. (2012). The phytochemistry and biological activity of secondary metabolites from Kenyan Vernonia and Vepris species. PhD Thesis, University of Kwazulu-Natal, South Africa,2012. [View] [PubMed]
Pubchem:
179651
Cas:
1180-71-8
Gnps:
CCMSLIB00004690463
Zinc:
ZINC000004096134
Kegg Ligand:
C03514
Chebi:
16226
Nmrshiftdb2:
60022666
Metabolights:
MTBLC16226
Chembl:
CHEMBL517449
Comptox:
DTXSID8045985
Selleck:
Limonin
CPRiL:
57674
SMILES: c1occc1C(OC(=O)C(C234)O4)C3CCC5C67C(CC(=O)C25)COC6CC(=O)OC7
Level: 1
Mol. Weight: 470.52 g/mol
SMILES: C123C(O3)C(=O)OCC2CCC4C56C(CC(=O)C14)COC5CC(=O)OC6
Level: 0
Mol. Weight: 470.52 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 470.52 g/mol
Antibacterial
Larvicidal
Absorption
- Caco-2 (logPapp)
- -5.25
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.01
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.92
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.54
- Plasma Protein Binding
- 46.43
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 10.21
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.09
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.41
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.53
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -369.68
- Rat (Acute)
- 5.04
- Rat (Chronic Oral)
- 1.9
- Fathead Minnow
- 3.94
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 511.08
- Hydration Free Energy
- -2.99
- Log(D) at pH=7.4
- 2.16
- Log(P)
- 2.2
- Log S
- -5.3
- Log(Vapor Pressure)
- -9.75
- Melting Point
- 288.95
- pKa Acid
- 3.84
- pKa Basic
- 4.1
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7345 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7345 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P05108 | CP11A_HUMAN | Homo sapiens | 3 | 0.7325 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P05108 | CP11A_HUMAN | Homo sapiens | 3 | 0.7325 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7278 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7278 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7222 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7222 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7217 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7217 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 2 | 0.7200 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 2 | 0.7200 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7181 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7181 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7179 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7179 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P00189 | CP11A_BOVIN | Bos taurus | 3 | 0.7165 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P00189 | CP11A_BOVIN | Bos taurus | 3 | 0.7165 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7112 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7112 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 2 | 0.7071 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 2 | 0.7071 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7067 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7067 |
| Pyruvate:ferredoxin oxidoreductase | P94692 | PFOR_DESAF | Desulfocurvibacter africanus | 3 | 0.7022 |
| Pyruvate:ferredoxin oxidoreductase | P94692 | PFOR_DESAF | Desulfocurvibacter africanus | 3 | 0.7022 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7019 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7019 |