[(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-acetyloxy-4-ethoxy-8-(furan-3-yl)-12-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.02,11.06,10.016,20]icos-9-en-19-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: d6c10acc-f85e-45f6-9072-89cae70051ed
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-acetyloxy-4-ethoxy-8-(furan-3-yl)-12-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.02,11.06,10.016,20]icos-9-en-19-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CCOC1CC2C3(C(CC(C4(C3C(C(C2(C5=C(C(CC5O1)C6=COC=C6)C)C)O)OC4)C)OC(=O)C)OC(=O)C(=CC)C)C
• SMILES (Isomeric): CCO[C@H]1C[C@@H]2[C@]3([C@H](C[C@H]([C@@]4([C@@H]3[C@H]([C@H]([C@]2(C5=C([C@@H](C[C@@H]5O1)C6=COC=C6)C)C)O)OC4)C)OC(=O)C)OC(=O)/C(=C/C)/C)C
• InChI: InChI=1S/C35H48O9/c1-9-18(3)32(38)44-26-15-25(42-20(5)36)33(6)17-41-29-30(33)34(26,7)24-14-27(40-10-2)43-23-13-22(21-11-12-39-16-21)19(4)28(23)35(24,8)31(29)37/h9,11-12,16,22-27,29-31,37H,10,13-15,17H2,1-8H3/b18-9+/t22-,23+,24-,25-,26+,27-,29-,30+,31-,33-,34+,35-/m1/s1
• InChI Key: DJLOIVPDTPRBMS-WHAOCMSESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₈O₉
• Molecular Weight: 612.70 g/mol
• Exact Mass: 612.32983310 g/mol
• Topological Polar Surface Area (TPSA): 114.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 5.47
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9906	99.06%
Caco-2	-	0.7843	78.43%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7554	75.54%
OATP2B1 inhibitior	-	0.7213	72.13%
OATP1B1 inhibitior	+	0.7591	75.91%
OATP1B3 inhibitior	+	0.8789	87.89%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9961	99.61%
P-glycoprotein inhibitior	+	0.8115	81.15%
P-glycoprotein substrate	+	0.6638	66.38%
CYP3A4 substrate	+	0.7322	73.22%
CYP2C9 substrate	-	0.7965	79.65%
CYP2D6 substrate	-	0.8876	88.76%
CYP3A4 inhibition	+	0.5317	53.17%
CYP2C9 inhibition	-	0.6984	69.84%
CYP2C19 inhibition	-	0.7049	70.49%
CYP2D6 inhibition	-	0.9439	94.39%
CYP1A2 inhibition	-	0.8169	81.69%
CYP2C8 inhibition	+	0.8317	83.17%
CYP inhibitory promiscuity	-	0.5795	57.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4228	42.28%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9083	90.83%
Skin irritation	-	0.5919	59.19%
Skin corrosion	-	0.9464	94.64%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7652	76.52%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8733	87.33%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.4653	46.53%
Acute Oral Toxicity (c)	I	0.4959	49.59%
Estrogen receptor binding	+	0.8214	82.14%
Androgen receptor binding	+	0.7156	71.56%
Thyroid receptor binding	+	0.5392	53.92%
Glucocorticoid receptor binding	+	0.7793	77.93%
Aromatase binding	+	0.7185	71.85%
PPAR gamma	+	0.7715	77.15%
Honey bee toxicity	-	0.6511	65.11%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.23%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	96.88%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.02%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.01%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.82%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.57%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.06%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.10%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.19%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.28%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	84.89%	94.73%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	84.54%	81.11%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	84.27%	87.67%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.92%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.67%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.28%	97.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.23%	99.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.81%	93.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.06%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.02%	95.56%

Plants that contains it

• Melia azedarach

Cross-Links

• PubChem: 56950633
• NPASS: NPC264690