[(1S,2R,4R,5R,6S,8R,10S,11S,12R,14R,15R,16S,19R,20R,21S)-4,20,21-triacetyloxy-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-16-yl] (2R)-2-methylbutanoate

Details

• Internal ID: ff992152-8d54-4b41-a24b-c687c8ab0153
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1S,2R,4R,5R,6S,8R,10S,11S,12R,14R,15R,16S,19R,20R,21S)-4,20,21-triacetyloxy-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-16-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C2(C3CC(C4(C(C3(CO1)C(C(C2OC(=O)C)OC(=O)C)O)C(=O)C(C5(C46C(O6)CC5C7=COC=C7)C)OC(=O)C)C)O)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@H]1[C@@]2([C@@H]3C[C@H]([C@@]4([C@@H]([C@@]3(CO1)[C@H]([C@H]([C@H]2OC(=O)C)OC(=O)C)O)C(=O)[C@@H]([C@@]5([C@]46[C@H](O6)C[C@H]5C7=COC=C7)C)OC(=O)C)C)O)C
• InChI: InChI=1S/C37H48O14/c1-9-16(2)31(44)50-32-33(6)22-13-23(41)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)12-24-37(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-/m1/s1
• InChI Key: AVSOCPWJWLVCAL-FNYJTGHVSA-N
• Popularity: 0 references 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): 198.00 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	+	0.9702	97.02%
Caco-2	-	0.8369	83.69%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7248	72.48%
OATP2B1 inhibitior	-	0.7203	72.03%
OATP1B1 inhibitior	+	0.6862	68.62%
OATP1B3 inhibitior	+	0.8252	82.52%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9666	96.66%
P-glycoprotein inhibitior	+	0.8065	80.65%
P-glycoprotein substrate	+	0.6758	67.58%
CYP3A4 substrate	+	0.7067	70.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8322	83.22%
CYP3A4 inhibition	+	0.6602	66.02%
CYP2C9 inhibition	-	0.7598	75.98%
CYP2C19 inhibition	-	0.8361	83.61%
CYP2D6 inhibition	-	0.9481	94.81%
CYP1A2 inhibition	-	0.8754	87.54%
CYP2C8 inhibition	+	0.7202	72.02%
CYP inhibitory promiscuity	-	0.7882	78.82%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5334	53.34%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9060	90.60%
Skin irritation	-	0.7064	70.64%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	-	0.5455	54.55%
Human Ether-a-go-go-Related Gene inhibition	+	0.6590	65.90%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5677	56.77%
skin sensitisation	-	0.8882	88.82%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6284	62.84%
Acute Oral Toxicity (c)	I	0.4393	43.93%
Estrogen receptor binding	+	0.8147	81.47%
Androgen receptor binding	+	0.7548	75.48%
Thyroid receptor binding	+	0.5696	56.96%
Glucocorticoid receptor binding	+	0.7933	79.33%
Aromatase binding	+	0.6969	69.69%
PPAR gamma	+	0.7839	78.39%
Honey bee toxicity	-	0.6795	67.95%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
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	98.54%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.42%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	97.64%	90.17%
CHEMBL2581	P07339	Cathepsin D	97.55%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.42%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.02%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.88%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	91.82%	83.82%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.07%	96.77%
CHEMBL3922	P50579	Methionine aminopeptidase 2	90.33%	97.28%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.09%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.45%	95.56%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	87.49%	95.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.23%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.96%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	85.37%	97.79%
CHEMBL340	P08684	Cytochrome P450 3A4	85.16%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.38%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.01%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	84.00%	94.73%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.43%	82.69%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.42%	98.75%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.76%	96.47%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.70%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.97%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.37%	100.00%

Plants that contains it

• Melia azedarach

Cross-Links

• PubChem: 163185099
• LOTUS: LTS0227182
• wikiData: Q104919774