[(2R,3R,5R)-5-[(2S)-3,3-dimethyloxiran-2-yl]-3-[(1R,2R,8R,10R,11R,15S,16S)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.02,8.012,16]octadec-12-en-15-yl]oxolan-2-yl] acetate

Details

• Internal ID: dfe99cf6-88e0-458d-83dc-83481ccd7de3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(2R,3R,5R)-5-[(2S)-3,3-dimethyloxiran-2-yl]-3-[(1R,2R,8R,10R,11R,15S,16S)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.02,8.012,16]octadec-12-en-15-yl]oxolan-2-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(CC(O1)C2C(O2)(C)C)C3CC=C4C3(CCC5C4(C(CC6C5(CCC(=O)OC6(C)C)C)O)C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@H](C[C@@H](O1)[C@H]2C(O2)(C)C)[C@@H]3CC=C4[C@]3(CC[C@H]5[C@]4([C@@H](C[C@@H]6[C@@]5(CCC(=O)OC6(C)C)C)O)C)C
• InChI: InChI=1S/C32H48O7/c1-17(33)36-27-18(15-20(37-27)26-29(4,5)39-26)19-9-10-21-30(19,6)13-11-22-31(7)14-12-25(35)38-28(2,3)23(31)16-24(34)32(21,22)8/h10,18-20,22-24,26-27,34H,9,11-16H2,1-8H3/t18-,19+,20-,22-,23+,24-,26+,27+,30+,31-,32+/m1/s1
• InChI Key: XFBKYNDAKVXPHE-NITHGSSBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₈O₇
• Molecular Weight: 544.70 g/mol
• Exact Mass: 544.34000387 g/mol
• Topological Polar Surface Area (TPSA): 94.60 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 5.33
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	-	0.7213	72.13%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7955	79.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8587	85.87%
OATP1B3 inhibitior	+	0.8464	84.64%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8699	86.99%
P-glycoprotein inhibitior	+	0.7627	76.27%
P-glycoprotein substrate	-	0.5873	58.73%
CYP3A4 substrate	+	0.7403	74.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8656	86.56%
CYP3A4 inhibition	+	0.5189	51.89%
CYP2C9 inhibition	-	0.7090	70.90%
CYP2C19 inhibition	-	0.8148	81.48%
CYP2D6 inhibition	-	0.9367	93.67%
CYP1A2 inhibition	-	0.7225	72.25%
CYP2C8 inhibition	+	0.6995	69.95%
CYP inhibitory promiscuity	-	0.8984	89.84%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4140	41.40%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9363	93.63%
Skin irritation	-	0.5127	51.27%
Skin corrosion	-	0.9092	90.92%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6968	69.68%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8259	82.59%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.6026	60.26%
Acute Oral Toxicity (c)	I	0.4890	48.90%
Estrogen receptor binding	+	0.6821	68.21%
Androgen receptor binding	+	0.7194	71.94%
Thyroid receptor binding	+	0.5577	55.77%
Glucocorticoid receptor binding	+	0.7212	72.12%
Aromatase binding	+	0.7237	72.37%
PPAR gamma	+	0.6627	66.27%
Honey bee toxicity	-	0.6926	69.26%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9944	99.44%

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	96.45%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.48%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.85%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	92.68%	83.82%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.61%	100.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	92.25%	89.05%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.85%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	89.17%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.06%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.84%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.11%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.69%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.32%	85.14%
CHEMBL1937	Q92769	Histone deacetylase 2	83.11%	94.75%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.37%	93.04%
CHEMBL1871	P10275	Androgen Receptor	82.31%	96.43%
CHEMBL5028	O14672	ADAM10	81.94%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	81.40%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.94%	91.24%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.38%	97.14%

Plants that contains it

• Luvunga sarmentosa

Cross-Links

• PubChem: 101193284
• LOTUS: LTS0070645
• wikiData: Q105326910