methyl 2-[(1R,2R,6S,7R,8R,9R,10R,12S,14R,15S,16S,17R,18S,19R,20R)-8,18-diacetyloxy-15-(acetyloxymethyl)-6-(furan-3-yl)-9,19,20-trihydroxy-7,12,17-trimethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.114,17.01,10.02,7.010,15.014,19]docosan-16-yl]acetate

Details

• Internal ID: 80ba39ae-fca4-4fda-bab4-3fdd25572d2d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: methyl 2-[(1R,2R,6S,7R,8R,9R,10R,12S,14R,15S,16S,17R,18S,19R,20R)-8,18-diacetyloxy-15-(acetyloxymethyl)-6-(furan-3-yl)-9,19,20-trihydroxy-7,12,17-trimethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.114,17.01,10.02,7.010,15.014,19]docosan-16-yl]acetate
• SMILES (Canonical): CC(=O)OCC12C(C3(CC14C(C3OC(=O)C)(C(C56C2(C(C(C7(C5CC(=O)OC7C8=COC=C8)C)OC(=O)C)O)OC(O4)(O6)C)O)O)C)CC(=O)OC
• SMILES (Isomeric): CC(=O)OC[C@@]12[C@H]([C@]3(C[C@]14[C@]([C@H]3OC(=O)C)([C@H]([C@@]56[C@@]2([C@@H]([C@@H]([C@@]7([C@H]5CC(=O)O[C@H]7C8=COC=C8)C)OC(=O)C)O)O[C@@](O4)(O6)C)O)O)C)CC(=O)OC
• InChI: InChI=1S/C35H42O17/c1-15(36)46-14-31-19(10-21(39)44-7)28(4)13-32(31)33(43,27(28)48-17(3)38)26(42)34-20-11-22(40)49-24(18-8-9-45-12-18)29(20,5)25(47-16(2)37)23(41)35(31,34)52-30(6,50-32)51-34/h8-9,12,19-20,23-27,41-43H,10-11,13-14H2,1-7H3/t19-,20+,23+,24-,25-,26+,27-,28+,29+,30-,31+,32+,33+,34+,35-/m0/s1
• InChI Key: XQYBLSBUGMZEFP-MKSOBYFMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₂O₁₇
• Molecular Weight: 734.70 g/mol
• Exact Mass: 734.24219987 g/mol
• Topological Polar Surface Area (TPSA): 233.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): 0.35
• H-Bond Acceptor: 17
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9085	90.85%
Caco-2	-	0.8326	83.26%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7837	78.37%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	-	0.4364	43.64%
OATP1B3 inhibitior	+	0.8247	82.47%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9605	96.05%
P-glycoprotein inhibitior	+	0.7635	76.35%
P-glycoprotein substrate	+	0.7231	72.31%
CYP3A4 substrate	+	0.7206	72.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8377	83.77%
CYP3A4 inhibition	-	0.7869	78.69%
CYP2C9 inhibition	-	0.8409	84.09%
CYP2C19 inhibition	-	0.8384	83.84%
CYP2D6 inhibition	-	0.9486	94.86%
CYP1A2 inhibition	-	0.8665	86.65%
CYP2C8 inhibition	+	0.8033	80.33%
CYP inhibitory promiscuity	-	0.8904	89.04%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6067	60.67%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.8872	88.72%
Skin irritation	-	0.7710	77.10%
Skin corrosion	-	0.9437	94.37%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7189	71.89%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.5771	57.71%
skin sensitisation	-	0.8996	89.96%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5527	55.27%
Acute Oral Toxicity (c)	I	0.4395	43.95%
Estrogen receptor binding	+	0.7824	78.24%
Androgen receptor binding	+	0.7701	77.01%
Thyroid receptor binding	+	0.5958	59.58%
Glucocorticoid receptor binding	+	0.7038	70.38%
Aromatase binding	+	0.7007	70.07%
PPAR gamma	+	0.7324	73.24%
Honey bee toxicity	-	0.7303	73.03%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.9889	98.89%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.75%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	98.92%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.63%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.15%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.64%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.53%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	93.05%	91.49%
CHEMBL2996	Q05655	Protein kinase C delta	91.87%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.67%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.82%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.42%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.78%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	87.52%	91.19%
CHEMBL5028	O14672	ADAM10	87.51%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.58%	99.23%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.77%	91.24%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.58%	95.71%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.08%	94.80%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.39%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.37%	92.62%
CHEMBL332	P03956	Matrix metalloproteinase-1	81.07%	94.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.99%	99.17%
CHEMBL299	P17252	Protein kinase C alpha	80.82%	98.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.79%	97.14%
CHEMBL221	P23219	Cyclooxygenase-1	80.65%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.41%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.24%	95.56%

Plants that contains it

• Chukrasia tabularis

Cross-Links

• PubChem: 154497548
• LOTUS: LTS0168115
• wikiData: Q105340217