4-[(3R,3aR,6S,6aR)-3-(3,4-dihydroxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]benzene-1,2-diol

Details

• Internal ID: 65228309-0df6-4348-9958-9ba818ae845e
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans
• IUPAC Name: 4-[(3R,3aR,6S,6aR)-3-(3,4-dihydroxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]benzene-1,2-diol
• SMILES (Canonical): C1C2C(COC2C3=CC(=C(C=C3)O)O)C(O1)C4=CC(=C(C=C4)O)O
• SMILES (Isomeric): C1[C@H]2[C@H](CO[C@@H]2C3=CC(=C(C=C3)O)O)[C@@H](O1)C4=CC(=C(C=C4)O)O
• InChI: InChI=1S/C18H18O6/c19-13-3-1-9(5-15(13)21)17-11-7-24-18(12(11)8-23-17)10-2-4-14(20)16(22)6-10/h1-6,11-12,17-22H,7-8H2/t11-,12-,17-,18+/m0/s1
• InChI Key: OQSOTSIYXPYTRE-GNTOHDJUSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈O₆
• Molecular Weight: 330.30 g/mol
• Exact Mass: 330.11033829 g/mol
• Topological Polar Surface Area (TPSA): 99.40 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• EC-2
• BDBM50443540

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9749	97.49%
Caco-2	-	0.5241	52.41%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8036	80.36%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.9715	97.15%
OATP1B3 inhibitior	+	0.9656	96.56%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7632	76.32%
P-glycoprotein inhibitior	-	0.5648	56.48%
P-glycoprotein substrate	-	0.9830	98.30%
CYP3A4 substrate	-	0.6596	65.96%
CYP2C9 substrate	-	0.7786	77.86%
CYP2D6 substrate	+	0.3664	36.64%
CYP3A4 inhibition	-	0.7978	79.78%
CYP2C9 inhibition	+	0.6290	62.90%
CYP2C19 inhibition	+	0.5454	54.54%
CYP2D6 inhibition	-	0.7870	78.70%
CYP1A2 inhibition	+	0.6984	69.84%
CYP2C8 inhibition	-	0.7463	74.63%
CYP inhibitory promiscuity	+	0.6425	64.25%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9008	90.08%
Carcinogenicity (trinary)	Non-required	0.4698	46.98%
Eye corrosion	-	0.9910	99.10%
Eye irritation	+	0.7433	74.33%
Skin irritation	-	0.7124	71.24%
Skin corrosion	-	0.9531	95.31%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7808	78.08%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.6925	69.25%
skin sensitisation	-	0.7962	79.62%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8762	87.62%
Acute Oral Toxicity (c)	III	0.5413	54.13%
Estrogen receptor binding	+	0.8195	81.95%
Androgen receptor binding	+	0.7364	73.64%
Thyroid receptor binding	+	0.6857	68.57%
Glucocorticoid receptor binding	+	0.6046	60.46%
Aromatase binding	+	0.5194	51.94%
PPAR gamma	+	0.6586	65.86%
Honey bee toxicity	-	0.9028	90.28%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9844	98.44%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	21860 nM	IC50	PMID: 25129171

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.09%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.43%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.81%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.94%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.53%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.96%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.87%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.63%	92.94%

Plants that contains it

• Morinda citrifolia

Cross-Links

• PubChem: 53321379
• NPASS: NPC257682
• ChEMBL: CHEMBL1688937
• LOTUS: LTS0141124
• wikiData: Q105197196