Limonin

Details

• Internal ID: f3c0323d-9a21-4227-a817-54fdc6b2a7d5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• 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
• SMILES (Canonical): CC1(C2CC(=O)C3(C(C24COC(=O)CC4O1)CCC5(C36C(O6)C(=O)OC5C7=COC=C7)C)C)C
• SMILES (Isomeric): 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
• 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
• InChI Key: KBDSLGBFQAGHBE-MSGMIQHVSA-N
• Popularity: 247 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀O₈
• Molecular Weight: 470.50 g/mol
• Exact Mass: 470.19406791 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 3.14
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 1180-71-8
• Dictamnolactone
• Obaculactone
• Citrolimonin
• Evodin
• Limonine
• 7,16-Dioxo-7,16-dideoxylimondiol
• Limoni
• Limonoic acid 3,19:16,17 dilactone
• Limonoic acid, di-delta-lactone
• limonoic acid di-delta-lactone
• NSC 36508
• limonoic acid 3,19:16,17-dilactone
• Evodia fruit
• Limonoate D-ring-lactone
• CCRIS 4047
• (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
• UNII-L0F260866S
• CHEBI:16226
• Limonoic acid, di-.delta.-lactone
• L0F260866S
• AI3-37932
• (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
• 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-
• DTXCID6025985
• Limone
• MFCD00075922
• (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,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)-
• 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
• 3-furyl(tetramethyl)[?]trione
• Linonin
• NSC36508
• NSC-36508
• NCGC00095714-01
• 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-
• LIMONIN [MI]
• 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
• ACon1_001996
• KBio3_001983
• Limonoic acid di-.delta.-lactone
• KBDSLGBFQAGHBE-MSGMIQHVSA-N
• 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))-
• 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
• AS-15249
• HY-17411
• L0258
• Limonin, from citrus seeds, >90% (HPLC)
• S2319
• C03514
• A854522
• Q-100083
• Q2398745
• BRD-K05906022-001-03-6
• BRD-K05906022-001-05-1
• Limone; Citrolimonin; Evodine; Dictamnolactone; Obaculactone
• (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-(furan-3-yl)-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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9772	97.72%
Caco-2	-	0.7064	70.64%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8017	80.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8567	85.67%
OATP1B3 inhibitior	+	0.9807	98.07%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9293	92.93%
P-glycoprotein inhibitior	+	0.7047	70.47%
P-glycoprotein substrate	-	0.5097	50.97%
CYP3A4 substrate	+	0.6615	66.15%
CYP2C9 substrate	-	0.6043	60.43%
CYP2D6 substrate	-	0.8231	82.31%
CYP3A4 inhibition	+	0.6355	63.55%
CYP2C9 inhibition	-	0.7868	78.68%
CYP2C19 inhibition	-	0.7920	79.20%
CYP2D6 inhibition	-	0.9335	93.35%
CYP1A2 inhibition	-	0.7993	79.93%
CYP2C8 inhibition	+	0.6528	65.28%
CYP inhibitory promiscuity	-	0.9312	93.12%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6118	61.18%
Eye corrosion	-	0.9873	98.73%
Eye irritation	+	0.7346	73.46%
Skin irritation	-	0.7520	75.20%
Skin corrosion	-	0.9028	90.28%
Ames mutagenesis	-	0.5454	54.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7442	74.42%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.6945	69.45%
skin sensitisation	-	0.8635	86.35%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.7839	78.39%
Acute Oral Toxicity (c)	III	0.4425	44.25%
Estrogen receptor binding	+	0.8670	86.70%
Androgen receptor binding	+	0.8652	86.52%
Thyroid receptor binding	+	0.6744	67.44%
Glucocorticoid receptor binding	+	0.8970	89.70%
Aromatase binding	+	0.8685	86.85%
PPAR gamma	+	0.7464	74.64%
Honey bee toxicity	-	0.8114	81.14%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9904	99.04%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	23200 nM	Ki	PMID: 16248836

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.83%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.38%	97.09%
CHEMBL3524	P56524	Histone deacetylase 4	91.42%	92.97%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.00%	96.09%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	88.95%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.05%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.89%	100.00%
CHEMBL2581	P07339	Cathepsin D	87.52%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.53%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.64%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.22%	94.45%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	83.70%	85.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.03%	95.56%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	82.25%	96.00%
CHEMBL301	P24941	Cyclin-dependent kinase 2	81.72%	91.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.28%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.66%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.26%	95.89%

Plants that contains it

• Aeollanthus buchnerianus
• Aframomum daniellii
• Ageratina saltillensis
• Agnorhiza bolanderi
• Alchornea cordifolia
• Anaxagorea crassipetala
• Araujia sericifera
• Arnica nevadensis
• Artemisia gmelinii
• Atalantia wightii
• Balanophora japonica
• Berberis repens
• Beyeria sulcata var. brevipes
• Bursaria spinosa
• Chloranthus tianmushanensis
• Chromolaena odorata
• Chromolaena pulchella
• Citrus × aurantium
• Citrus cavaleriei
• Citrus deliciosa
• Citrus hystrix
• Citrus maxima
• Citrus medica
• Citrus trifoliata
• Clausena anisata
• Coptis chinensis
• Corydalis persica
• Corynanthe pachyceras
• Cota tinctoria
• Craibia grandiflora
• Cynoglossum amabile
• Cynoglossum viridiflorum
• Dendrosenecio kilimanjari
• Dictamnus albus
• Dictamnus dasycarpus
• Dipterocarpus alatus
• Drosera peltata
• Echinops amplexicaulis
• Echium plantagineum
• Esenbeckia hartmanii
• Fagaropsis glabra
• Ficus formosana
• Flacourtia jangomas
• Gardenia fosbergii
• Glycosmis parva
• Glycosmis pseudoracemosa
• Grewia villosa
• Helianthus niveus
• Hernandia sonora
• Ilex affinis
• Iphiona grantioides
• Isodon umbrosus
• Juniperus horizontalis
• Kaempferia pulchra
• Lathyrus tingitanus
• Leptospermum recurvum
• Litogyne gariepina
• Luvunga sarmentosa
• Murraya paniculata
• Odixia angusta
• Persicaria tinctoria
• Phellodendron amurense
• Phellodendron chinense
• Plectranthus caninus
• Prosopis glandulosa
• Prunus laurocerasus
• Pteris plumieri
• Pycnarrhena novoguineensis
• Quassia bidwillii
• Quercus cerris
• Raulinoa echinata
• Rauvolfia salicifolia
• Salta triflora
• Salvia officinalis
• Salvia polystachya
• Senecio squalidus
• Seriphidium cinum
• Sesbania punicea
• Simira eliezeriana
• Skimmia japonica
• Sorbus pallescens
• Spiranthera odoratissima
• Stenostomum lucidum
• Strychnos spinosa
• Taxodium huegelii
• Tetradium daniellii
• Tetradium glabrifolium
• Tetradium ruticarpum
• Tetradium trichotomum
• Thalictrum lucidum
• Trifolium montanum
• Vepris louisii
• Vepris suaveolens
• Vernonia chloropappa
• Vitex madiensis

Cross-Links

• PubChem: 179651
• NPASS: NPC305016
• ChEMBL: CHEMBL517449
• LOTUS: LTS0207873
• wikiData: Q2398745