(1R,2R,7S,10S,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

Details

• Internal ID: 861f9353-0739-4812-a0e4-6c7ee5e01cd0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: (1R,2R,7S,10S,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-BMJHCZSQSA-N
• Popularity: 3 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

There are no found synonyms.

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:

No proven targets yet!

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

• Ageratina saltillensis
• Agnorhiza bolanderi
• Anaxagorea crassipetala
• Araujia sericifera
• Arnica nevadensis
• Artemisia gmelinii
• Asterolasia squamuligera
• Beyeria sulcata var. brevipes
• Bidens andicola
• Bunium paucifolium
• Bursaria spinosa
• Catharanthus roseus
• Chloranthus tianmushanensis
• Chromolaena odorata
• Chromolaena pulchella
• Cinnamomum chekiangense
• Citrus × aurantium
• Craibia grandiflora
• Dendrosenecio kilimanjari
• Dictamnus dasycarpus
• Dipterocarpus alatus
• Drosera peltata
• Echinops amplexicaulis
• Esenbeckia hartmanii
• Ficus formosana
• Flacourtia jangomas
• Gardenia fosbergii
• Grewia villosa
• Ilex affinis
• Isodon umbrosus
• Kaempferia pulchra
• Ligularia hodgsonii
• Litogyne gariepina
• Moringa oleifera
• Odixia angusta
• Phellodendron amurense
• Pluchea dioscoridis
• Prosopis glandulosa
• Prunus laurocerasus
• Pteris plumieri
• Pyrola rotundifolia
• Quercus cerris
• Salta triflora
• Salvia officinalis
• Salvia polystachya
• Senecio squalidus
• Seriphidium cinum
• Sesbania punicea
• Simira eliezeriana
• Sorbus pallescens
• Stenostomum lucidum
• Stevia alpina
• Taxodium huegelii
• Trifolium montanum
• Vitex madiensis

Cross-Links

• PubChem: 92966492
• NPASS: NPC273756
• LOTUS: LTS0222914
• wikiData: Q105138119