methyl (1R,2S,3R,6R,8S,9S,13S,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-11-ene-17-carboxylate

Details

• Internal ID: 03fb6253-fe99-4f15-8aeb-63d19858c7c0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8S,9S,13S,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-11-ene-17-carboxylate
• SMILES (Canonical): CC1C2CC3C45COC(C4C(C(=O)O3)OC(=O)C=C(C)C(C)(C)OC(=O)C)(C(C(C5C2(C=C(C1=O)OC6C(C(C(C(O6)CO)O)O)O)C)O)O)C(=O)OC
• SMILES (Isomeric): C[C@H]1[C@@H]2C[C@@H]3[C@@]45CO[C@@]([C@@H]4[C@H](C(=O)O3)OC(=O)/C=C(\C)/C(C)(C)OC(=O)C)([C@H]([C@@H]([C@@H]5[C@]2(C=C(C1=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)O)O)C(=O)OC
• InChI: InChI=1S/C36H48O18/c1-13(33(4,5)54-15(3)38)8-20(39)53-26-28-35-12-49-36(28,32(47)48-7)29(45)25(44)27(35)34(6)10-17(21(40)14(2)16(34)9-19(35)52-30(26)46)50-31-24(43)23(42)22(41)18(11-37)51-31/h8,10,14,16,18-19,22-29,31,37,41-45H,9,11-12H2,1-7H3/b13-8+/t14-,16-,18+,19+,22+,23-,24+,25+,26+,27+,28+,29-,31+,34-,35+,36-/m0/s1
• InChI Key: YNYBTCKMNHXXGZ-CYIYFLOKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₈O₁₈
• Molecular Weight: 768.80 g/mol
• Exact Mass: 768.28406468 g/mol
• Topological Polar Surface Area (TPSA): 271.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -2.05
• H-Bond Acceptor: 18
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

• 95258-17-6
• AKOS040760762

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7012	70.12%
Caco-2	-	0.8687	86.87%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7392	73.92%
OATP2B1 inhibitior	-	0.8617	86.17%
OATP1B1 inhibitior	+	0.8205	82.05%
OATP1B3 inhibitior	+	0.9346	93.46%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8393	83.93%
P-glycoprotein inhibitior	+	0.7569	75.69%
P-glycoprotein substrate	+	0.7778	77.78%
CYP3A4 substrate	+	0.7300	73.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8918	89.18%
CYP3A4 inhibition	-	0.8951	89.51%
CYP2C9 inhibition	-	0.8400	84.00%
CYP2C19 inhibition	-	0.8450	84.50%
CYP2D6 inhibition	-	0.9304	93.04%
CYP1A2 inhibition	-	0.8917	89.17%
CYP2C8 inhibition	+	0.6794	67.94%
CYP inhibitory promiscuity	-	0.8718	87.18%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5995	59.95%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9094	90.94%
Skin irritation	-	0.7143	71.43%
Skin corrosion	-	0.9347	93.47%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3732	37.32%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5198	51.98%
skin sensitisation	-	0.8488	84.88%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5052	50.52%
Acute Oral Toxicity (c)	III	0.5883	58.83%
Estrogen receptor binding	+	0.8019	80.19%
Androgen receptor binding	+	0.7422	74.22%
Thyroid receptor binding	+	0.5266	52.66%
Glucocorticoid receptor binding	+	0.7800	78.00%
Aromatase binding	+	0.6864	68.64%
PPAR gamma	+	0.7624	76.24%
Honey bee toxicity	-	0.6017	60.17%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9128	91.28%

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	99.66%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.09%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.26%	96.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	97.08%	89.34%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.94%	96.00%
CHEMBL2581	P07339	Cathepsin D	95.38%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.68%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	91.98%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.81%	86.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.88%	91.24%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.33%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.10%	94.45%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.88%	91.07%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.51%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.85%	89.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.65%	97.33%
CHEMBL5028	O14672	ADAM10	85.12%	97.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.49%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.93%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.83%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.58%	94.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.02%	96.61%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.01%	96.90%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.87%	97.14%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.52%	96.95%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.15%	89.50%

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: 101659161
• NPASS: NPC227438
• LOTUS: LTS0184098
• wikiData: Q105351158