4-[6-[2-(3,4-Dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]benzene-1,2-diol

Details

• Internal ID: 4aea72e4-68fb-4b9c-942c-19f54b160821
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans
• IUPAC Name: 4-[6-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]benzene-1,2-diol
• SMILES (Canonical): C1C2C(COC2C3=CC4=C(C=C3)OC(C(O4)CO)C5=CC(=C(C=C5)O)O)C(O1)C6=CC(=C(C=C6)O)O
• SMILES (Isomeric): C1C2C(COC2C3=CC4=C(C=C3)OC(C(O4)CO)C5=CC(=C(C=C5)O)O)C(O1)C6=CC(=C(C=C6)O)O
• InChI: InChI=1S/C27H26O9/c28-10-24-27(14-2-5-19(30)21(32)8-14)36-22-6-3-15(9-23(22)35-24)26-17-12-33-25(16(17)11-34-26)13-1-4-18(29)20(31)7-13/h1-9,16-17,24-32H,10-12H2
• InChI Key: RSGUJBLAYQHQGR-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₆O₉
• Molecular Weight: 494.50 g/mol
• Exact Mass: 494.15768240 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 3.46
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9259	92.59%
Caco-2	-	0.8916	89.16%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8128	81.28%
OATP2B1 inhibitior	-	0.7135	71.35%
OATP1B1 inhibitior	+	0.9314	93.14%
OATP1B3 inhibitior	+	0.9662	96.62%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5839	58.39%
P-glycoprotein inhibitior	+	0.6456	64.56%
P-glycoprotein substrate	-	0.9431	94.31%
CYP3A4 substrate	-	0.5303	53.03%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	+	0.3628	36.28%
CYP3A4 inhibition	-	0.8224	82.24%
CYP2C9 inhibition	-	0.7581	75.81%
CYP2C19 inhibition	-	0.6235	62.35%
CYP2D6 inhibition	-	0.8214	82.14%
CYP1A2 inhibition	-	0.6502	65.02%
CYP2C8 inhibition	-	0.7122	71.22%
CYP inhibitory promiscuity	-	0.5058	50.58%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5442	54.42%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.8491	84.91%
Skin irritation	-	0.7896	78.96%
Skin corrosion	-	0.9579	95.79%
Ames mutagenesis	+	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7978	79.78%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.6425	64.25%
skin sensitisation	-	0.8356	83.56%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.8191	81.91%
Acute Oral Toxicity (c)	III	0.4976	49.76%
Estrogen receptor binding	+	0.7753	77.53%
Androgen receptor binding	+	0.7442	74.42%
Thyroid receptor binding	+	0.6395	63.95%
Glucocorticoid receptor binding	-	0.4653	46.53%
Aromatase binding	+	0.5491	54.91%
PPAR gamma	+	0.7644	76.44%
Honey bee toxicity	-	0.8329	83.29%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.8935	89.35%

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	99.49%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.79%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.30%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	91.61%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.10%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.62%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.38%	99.15%

Plants that contains it

• Capparis flavicans
• Joannesia princeps

Cross-Links

• PubChem: 74963247
• LOTUS: LTS0230912
• wikiData: Q104400143