Acetic acid [(2S)-2alpha,5alpha-bis(4-methoxy-1,3-benzodioxole-6-yl)-4alpha-(hydroxymethyl)tetrahydrofuran]-3beta-ylmethyl ester

Details

• Internal ID: e39af86f-ca5b-4408-8ee8-6ec138ff6c10
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 7,7-epoxylignans
• IUPAC Name: [(2S,3R,4R,5R)-4-(hydroxymethyl)-2,5-bis(7-methoxy-1,3-benzodioxol-5-yl)oxolan-3-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(OC1C2=CC3=C(C(=C2)OC)OCO3)C4=CC5=C(C(=C4)OC)OCO5)CO
• SMILES (Isomeric): CC(=O)OC[C@H]1[C@@H]([C@@H](O[C@@H]1C2=CC3=C(C(=C2)OC)OCO3)C4=CC5=C(C(=C4)OC)OCO5)CO
• InChI: InChI=1S/C24H26O10/c1-12(26)29-9-16-15(8-25)21(13-4-17(27-2)23-19(6-13)30-10-32-23)34-22(16)14-5-18(28-3)24-20(7-14)31-11-33-24/h4-7,15-16,21-22,25H,8-11H2,1-3H3/t15-,16-,21-,22+/m0/s1
• InChI Key: YPQDTAINIDFHAR-WWLNLUSPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₆O₁₀
• Molecular Weight: 474.50 g/mol
• Exact Mass: 474.15259702 g/mol
• Topological Polar Surface Area (TPSA): 111.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.76
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• BDBM50250270
• 7,8-trans-8,8''-trans-7'',8''-cis-7,7''-bis(5-methoxy-3,4-methylenedioxyphenyl)-8-acetoxymethyl-8''-hydroxymethyltetrahydrofuran
• Acetic acid [(2S)-2alpha,5alpha-bis(4-methoxy-1,3-benzodioxole-6-yl)-4alpha-(hydroxymethyl)tetrahydrofuran]-3beta-ylmethyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9713	97.13%
Caco-2	+	0.5229	52.29%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7263	72.63%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9131	91.31%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9852	98.52%
P-glycoprotein inhibitior	+	0.7565	75.65%
P-glycoprotein substrate	-	0.8966	89.66%
CYP3A4 substrate	+	0.5330	53.30%
CYP2C9 substrate	-	0.7943	79.43%
CYP2D6 substrate	-	0.8382	83.82%
CYP3A4 inhibition	+	0.7577	75.77%
CYP2C9 inhibition	+	0.6919	69.19%
CYP2C19 inhibition	+	0.7234	72.34%
CYP2D6 inhibition	-	0.8392	83.92%
CYP1A2 inhibition	-	0.8474	84.74%
CYP2C8 inhibition	-	0.8022	80.22%
CYP inhibitory promiscuity	+	0.8429	84.29%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5062	50.62%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9336	93.36%
Skin irritation	-	0.7953	79.53%
Skin corrosion	-	0.9615	96.15%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3655	36.55%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.6100	61.00%
skin sensitisation	-	0.8289	82.89%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5443	54.43%
Acute Oral Toxicity (c)	III	0.4714	47.14%
Estrogen receptor binding	+	0.8011	80.11%
Androgen receptor binding	+	0.7380	73.80%
Thyroid receptor binding	+	0.5873	58.73%
Glucocorticoid receptor binding	+	0.8077	80.77%
Aromatase binding	-	0.5479	54.79%
PPAR gamma	+	0.6039	60.39%
Honey bee toxicity	-	0.7939	79.39%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9804	98.04%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL206	P03372	Estrogen receptor alpha	3100 nM	EC50	PMID: 16499324

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.83%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.78%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.06%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.33%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.89%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.85%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.56%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.49%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.33%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.13%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	87.74%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.72%	96.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.03%	96.77%
CHEMBL340	P08684	Cytochrome P450 3A4	85.09%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.08%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.78%	95.89%
CHEMBL2581	P07339	Cathepsin D	84.40%	98.95%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.33%	89.50%

Plants that contains it

• Metanarthecium luteoviride
• Pandanus tectorius
• Peperomia blanda
• Peperomia pellucida
• Sarcococca saligna

Cross-Links

• PubChem: 11554672
• NPASS: NPC166884
• ChEMBL: CHEMBL490350
• LOTUS: LTS0126543
• wikiData: Q105351779