5-[(3S,3aR,6S,6aR)-3-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-4-methyl-1,3-benzodioxole

Details

• Internal ID: aa3ad061-e7df-4227-8351-de29f66362af
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans
• IUPAC Name: 5-[(3S,3aR,6S,6aR)-3-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-4-methyl-1,3-benzodioxole
• SMILES (Canonical): CC1=C(C=CC2=C1OCO2)C3C4COC(C4CO3)C5=CC(=C(C=C5)OC)OC
• SMILES (Isomeric): CC1=C(C=CC2=C1OCO2)[C@@H]3[C@H]4CO[C@@H]([C@H]4CO3)C5=CC(=C(C=C5)OC)OC
• InChI: InChI=1S/C22H24O6/c1-12-14(5-7-18-20(12)28-11-27-18)22-16-10-25-21(15(16)9-26-22)13-4-6-17(23-2)19(8-13)24-3/h4-8,15-16,21-22H,9-11H2,1-3H3/t15-,16-,21+,22+/m0/s1
• InChI Key: MPPQCCFNXBGKFC-RZTYQLBFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₄O₆
• Molecular Weight: 384.40 g/mol
• Exact Mass: 384.15728848 g/mol
• Topological Polar Surface Area (TPSA): 55.40 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.82
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9859	98.59%
Caco-2	+	0.7078	70.78%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7071	70.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9185	91.85%
OATP1B3 inhibitior	+	0.9691	96.91%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8390	83.90%
P-glycoprotein inhibitior	+	0.7978	79.78%
P-glycoprotein substrate	-	0.7822	78.22%
CYP3A4 substrate	+	0.5907	59.07%
CYP2C9 substrate	-	0.7980	79.80%
CYP2D6 substrate	-	0.6891	68.91%
CYP3A4 inhibition	+	0.9131	91.31%
CYP2C9 inhibition	+	0.8069	80.69%
CYP2C19 inhibition	+	0.8992	89.92%
CYP2D6 inhibition	-	0.6569	65.69%
CYP1A2 inhibition	+	0.5689	56.89%
CYP2C8 inhibition	+	0.6373	63.73%
CYP inhibitory promiscuity	+	0.9415	94.15%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9208	92.08%
Carcinogenicity (trinary)	Non-required	0.4355	43.55%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.8893	88.93%
Skin irritation	-	0.8420	84.20%
Skin corrosion	-	0.9695	96.95%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8772	87.72%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.7172	71.72%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.7198	71.98%
Acute Oral Toxicity (c)	III	0.5522	55.22%
Estrogen receptor binding	+	0.8196	81.96%
Androgen receptor binding	+	0.7466	74.66%
Thyroid receptor binding	+	0.6456	64.56%
Glucocorticoid receptor binding	+	0.7042	70.42%
Aromatase binding	-	0.7277	72.77%
PPAR gamma	+	0.5560	55.60%
Honey bee toxicity	-	0.8163	81.63%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9890	98.90%

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	94.24%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.22%	95.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	93.14%	89.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.45%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.20%	86.33%
CHEMBL2535	P11166	Glucose transporter	91.11%	98.75%
CHEMBL2581	P07339	Cathepsin D	89.55%	98.95%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	88.65%	82.67%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.95%	92.62%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	87.25%	89.44%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.04%	92.94%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	86.95%	85.49%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	86.95%	94.03%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.58%	91.11%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	83.46%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.89%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.84%	97.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.79%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.79%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.64%	85.14%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.62%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.00%	96.00%

Plants that contains it

• Leucophyllum ambiguum

Cross-Links

• PubChem: 11025425
• LOTUS: LTS0022513
• wikiData: Q103815904