(1R,2S,3R,6R,8R,13S,14R,15R,16S,17R)-10,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylic acid

Details

• Internal ID: 9a9218f1-e341-4665-9979-33cbe5050f3f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: (1R,2S,3R,6R,8R,13S,14R,15R,16S,17R)-10,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylic acid
• SMILES (Canonical): CC1=C(C(=O)CC2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C)(OC5)C(=O)O)O)O)C)O
• SMILES (Isomeric): CC1=C(C(=O)C[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)(OC5)C(=O)O)O)O)C)O
• InChI: InChI=1S/C25H30O11/c1-9(2)5-14(27)36-17-19-24-8-34-25(19,22(32)33)20(30)16(29)18(24)23(4)7-12(26)15(28)10(3)11(23)6-13(24)35-21(17)31/h5,11,13,16-20,28-30H,6-8H2,1-4H3,(H,32,33)/t11-,13+,16+,17+,18+,19+,20-,23-,24+,25+/m0/s1
• InChI Key: RIYGDELXURVOBZ-HVCNMUSHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₀O₁₁
• Molecular Weight: 506.50 g/mol
• Exact Mass: 506.17881177 g/mol
• Topological Polar Surface Area (TPSA): 177.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.43
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8993	89.93%
Caco-2	-	0.8051	80.51%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8135	81.35%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.8549	85.49%
OATP1B3 inhibitior	+	0.9205	92.05%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8819	88.19%
P-glycoprotein inhibitior	-	0.4324	43.24%
P-glycoprotein substrate	+	0.8389	83.89%
CYP3A4 substrate	+	0.6928	69.28%
CYP2C9 substrate	-	0.8191	81.91%
CYP2D6 substrate	-	0.8935	89.35%
CYP3A4 inhibition	-	0.8683	86.83%
CYP2C9 inhibition	-	0.7973	79.73%
CYP2C19 inhibition	-	0.8751	87.51%
CYP2D6 inhibition	-	0.9396	93.96%
CYP1A2 inhibition	-	0.8667	86.67%
CYP2C8 inhibition	+	0.5209	52.09%
CYP inhibitory promiscuity	-	0.9039	90.39%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5995	59.95%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9111	91.11%
Skin irritation	-	0.6210	62.10%
Skin corrosion	-	0.9351	93.51%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5634	56.34%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.5323	53.23%
skin sensitisation	-	0.8505	85.05%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.8711	87.11%
Acute Oral Toxicity (c)	III	0.4965	49.65%
Estrogen receptor binding	+	0.7432	74.32%
Androgen receptor binding	+	0.6888	68.88%
Thyroid receptor binding	-	0.5622	56.22%
Glucocorticoid receptor binding	+	0.7554	75.54%
Aromatase binding	+	0.7222	72.22%
PPAR gamma	+	0.6529	65.29%
Honey bee toxicity	-	0.5827	58.27%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9932	99.32%

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	96.22%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	95.79%	83.82%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.33%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.25%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.91%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.81%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.27%	99.23%
CHEMBL2581	P07339	Cathepsin D	89.31%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.03%	85.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.85%	91.07%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.68%	96.95%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.54%	96.38%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.31%	96.77%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.17%	96.21%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.55%	89.34%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.01%	86.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.19%	93.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.87%	96.47%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	84.61%	97.88%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	84.03%	97.47%
CHEMBL340	P08684	Cytochrome P450 3A4	83.97%	91.19%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.52%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.40%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.27%	93.04%
CHEMBL5028	O14672	ADAM10	82.06%	97.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.67%	95.50%

Plants that contains it

• Asplenium normale
• Brucea javanica
• Carpobrotus edulis
• Castanea crenata
• Centrolobium tomentosum
• Ceratophyllum submersum
• Dracocephalum kotschyi
• Lippia carviodora
• Myrica nana
• Psilostrophe cooperi
• Sideritis tragoriganum
• Solanum jamaicense
• Trifolium alexandrinum

Cross-Links

• PubChem: 10391474
• NPASS: NPC312833
• LOTUS: LTS0125156
• wikiData: Q105237271