(9S,13S,17S,1R,3R,15R)-11,15,16-trihydroxy-17-(Methoxycarbonyl)-9,13-dimethyl-5,18-dioxa-4,12-dioxopentacyclo[12.5.0.0<1,6>.0<2,17>.0<8,13>]nonadec-10-en-3-yl (2E)-3,4-dimethylpent-2-enoate

Details

• Internal ID: f38e9095-9385-477d-a6a8-0b13cb098a79
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8S,9S,13S,14S,15R,16S,17R)-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-11,15,16-trihydroxy-9,13-dimethyl-4,12-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-10-ene-17-carboxylate
• SMILES (Canonical): CC1C=C(C(=O)C2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C(C)C)(OC5)C(=O)OC)O)O)C)O
• SMILES (Isomeric): C[C@@H]1C=C(C(=O)[C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@@]([C@@H]4[C@H](C(=O)O3)OC(=O)/C=C(\C)/C(C)C)(OC5)C(=O)OC)O)O)C)O
• InChI: InChI=1S/C28H36O11/c1-11(2)12(3)8-17(30)39-19-21-27-10-37-28(21,25(35)36-6)23(33)18(31)20(27)26(5)14(9-16(27)38-24(19)34)13(4)7-15(29)22(26)32/h7-8,11,13-14,16,18-21,23,29,31,33H,9-10H2,1-6H3/b12-8+/t13-,14+,16-,18-,19-,20-,21-,23+,26+,27-,28-/m1/s1
• InChI Key: PCKQDAAUYVCTJJ-GEUFJCQASA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₆O₁₁
• Molecular Weight: 548.60 g/mol
• Exact Mass: 548.22576196 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.01
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• (9S,13S,17S,1R,3R,15R)-11,15,16-trihydroxy-17-(Methoxycarbonyl)-9,13-dimethyl-5,18-dioxa-4,12-dioxopentacyclo[12.5.0.0<1,6>.0<2,17>.0<8,13>]nonadec-10-en-3-yl (2E)-3,4-dimethylpent-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9094	90.94%
Caco-2	-	0.7790	77.90%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8028	80.28%
OATP2B1 inhibitior	-	0.8613	86.13%
OATP1B1 inhibitior	+	0.8360	83.60%
OATP1B3 inhibitior	+	0.9545	95.45%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6656	66.56%
P-glycoprotein inhibitior	+	0.7020	70.20%
P-glycoprotein substrate	+	0.8483	84.83%
CYP3A4 substrate	+	0.7128	71.28%
CYP2C9 substrate	-	0.8191	81.91%
CYP2D6 substrate	-	0.8902	89.02%
CYP3A4 inhibition	-	0.7964	79.64%
CYP2C9 inhibition	-	0.8531	85.31%
CYP2C19 inhibition	-	0.8300	83.00%
CYP2D6 inhibition	-	0.9193	91.93%
CYP1A2 inhibition	-	0.8397	83.97%
CYP2C8 inhibition	+	0.5473	54.73%
CYP inhibitory promiscuity	-	0.8827	88.27%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5006	50.06%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.9146	91.46%
Skin irritation	-	0.6643	66.43%
Skin corrosion	-	0.9246	92.46%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5493	54.93%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8168	81.68%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5916	59.16%
Acute Oral Toxicity (c)	III	0.5269	52.69%
Estrogen receptor binding	+	0.8030	80.30%
Androgen receptor binding	+	0.6638	66.38%
Thyroid receptor binding	+	0.5374	53.74%
Glucocorticoid receptor binding	+	0.7631	76.31%
Aromatase binding	+	0.6758	67.58%
PPAR gamma	+	0.7090	70.90%
Honey bee toxicity	-	0.5349	53.49%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9606	96.06%

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	99.59%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.57%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	95.56%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.28%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.05%	96.00%
CHEMBL2581	P07339	Cathepsin D	93.46%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.28%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.66%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.12%	91.07%
CHEMBL1937	Q92769	Histone deacetylase 2	89.48%	94.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.43%	96.77%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.26%	98.75%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	87.01%	95.71%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.83%	96.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.49%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.26%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.21%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.71%	99.23%
CHEMBL4072	P07858	Cathepsin B	84.61%	93.67%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.56%	89.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.16%	97.33%
CHEMBL340	P08684	Cytochrome P450 3A4	84.10%	91.19%
CHEMBL2535	P11166	Glucose transporter	83.66%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.64%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.57%	90.71%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.81%	89.34%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.53%	94.33%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	80.98%	90.93%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.67%	97.28%

Plants that contains it

• Brucea antidysenterica

Cross-Links

• PubChem: 15953936
• LOTUS: LTS0108367
• wikiData: Q105205805