[(1S,2R,4R,5R,6S,8R,9R,10S,11R,13R,14R,15S,18R,19R,20S)-4,19,20-triacetyloxy-6-(furan-3-yl)-8,18-dihydroxy-5,10,14-trimethyl-3-oxo-16,21-dioxahexacyclo[12.3.3.19,11.01,13.02,10.05,9]henicosan-15-yl] 2-methylbutanoate

Details

• Internal ID: 18f6bbdb-e8f7-4377-8185-ecca39f617fa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1S,2R,4R,5R,6S,8R,9R,10S,11R,13R,14R,15S,18R,19R,20S)-4,19,20-triacetyloxy-6-(furan-3-yl)-8,18-dihydroxy-5,10,14-trimethyl-3-oxo-16,21-dioxahexacyclo[12.3.3.19,11.01,13.02,10.05,9]henicosan-15-yl] 2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C2(C3CC4C5(C(C3(CO1)C(C(C2OC(=O)C)OC(=O)C)O)C(=O)C(C6(C5(O4)C(CC6C7=COC=C7)O)C)OC(=O)C)C)C
• SMILES (Isomeric): CCC(C)C(=O)O[C@H]1[C@@]2([C@@H]3C[C@@H]4[C@@]5([C@@H]([C@@]3(CO1)[C@H]([C@H]([C@H]2OC(=O)C)OC(=O)C)O)C(=O)[C@@H]([C@@]6([C@@]5(O4)[C@@H](C[C@H]6C7=COC=C7)O)C)OC(=O)C)C)C
• InChI: InChI=1S/C37H48O14/c1-9-16(2)31(44)50-32-33(6)22-13-24-35(8)27(36(22,15-46-32)28(43)26(47-17(3)38)30(33)49-19(5)40)25(42)29(48-18(4)39)34(7)21(20-10-11-45-14-20)12-23(41)37(34,35)51-24/h10-11,14,16,21-24,26-30,32,41,43H,9,12-13,15H2,1-8H3/t16?,21-,22-,23+,24+,26+,27-,28-,29-,30+,32-,33+,34+,35+,36-,37-/m0/s1
• InChI Key: UEJRZXSOQCUTTA-WVIGIDJZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₄₈O₁₄
• Molecular Weight: 716.80 g/mol
• Exact Mass: 716.30440620 g/mol
• Topological Polar Surface Area (TPSA): 194.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.60
• H-Bond Acceptor: 14
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9672	96.72%
Caco-2	-	0.8385	83.85%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7270	72.70%
OATP2B1 inhibitior	-	0.7214	72.14%
OATP1B1 inhibitior	+	0.6911	69.11%
OATP1B3 inhibitior	+	0.8735	87.35%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9498	94.98%
P-glycoprotein inhibitior	+	0.8017	80.17%
P-glycoprotein substrate	+	0.6725	67.25%
CYP3A4 substrate	+	0.7063	70.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8288	82.88%
CYP3A4 inhibition	-	0.5617	56.17%
CYP2C9 inhibition	-	0.7930	79.30%
CYP2C19 inhibition	-	0.8363	83.63%
CYP2D6 inhibition	-	0.9499	94.99%
CYP1A2 inhibition	-	0.8659	86.59%
CYP2C8 inhibition	+	0.7275	72.75%
CYP inhibitory promiscuity	-	0.8290	82.90%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4829	48.29%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9075	90.75%
Skin irritation	-	0.7051	70.51%
Skin corrosion	-	0.9337	93.37%
Ames mutagenesis	-	0.5155	51.55%
Human Ether-a-go-go-Related Gene inhibition	-	0.3950	39.50%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.5734	57.34%
skin sensitisation	-	0.8946	89.46%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6361	63.61%
Acute Oral Toxicity (c)	III	0.4053	40.53%
Estrogen receptor binding	+	0.8049	80.49%
Androgen receptor binding	+	0.7545	75.45%
Thyroid receptor binding	+	0.5717	57.17%
Glucocorticoid receptor binding	+	0.8037	80.37%
Aromatase binding	+	0.6992	69.92%
PPAR gamma	+	0.7950	79.50%
Honey bee toxicity	-	0.6916	69.16%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9821	98.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.62%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.44%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.31%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.00%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	97.07%	90.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.90%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.73%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.61%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	91.06%	83.82%
CHEMBL3922	P50579	Methionine aminopeptidase 2	89.81%	97.28%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.96%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.39%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.12%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	86.73%	97.79%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.63%	95.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.93%	92.62%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.38%	98.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.98%	96.77%
CHEMBL340	P08684	Cytochrome P450 3A4	82.93%	91.19%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.66%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	82.26%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	81.65%	95.93%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.62%	82.69%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.49%	89.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.38%	100.00%

Plants that contains it

• Melia azedarach

Cross-Links

• PubChem: 101562405
• NPASS: NPC250842