4-hydroxy-9-(4-hydroxy-3,5-dimethoxy-phenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one

Details

• Internal ID: 0af56d3e-f072-43c7-a4c6-5e5ba52306d8
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones
• IUPAC Name: 4-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2C3C(CC4=C(C5=C(C=C24)OCO5)O)COC3=O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)C2C3C(CC4=C(C5=C(C=C24)OCO5)O)COC3=O
• InChI: InChI=1S/C21H20O8/c1-25-13-4-9(5-14(26-2)19(13)23)16-11-6-15-20(29-8-28-15)18(22)12(11)3-10-7-27-21(24)17(10)16/h4-6,10,16-17,22-23H,3,7-8H2,1-2H3
• InChI Key: JGGWNGRBXJWAOC-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₈
• Molecular Weight: 400.40 g/mol
• Exact Mass: 400.11581759 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.32
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• NSC659373
• TimTec1_004963
• Oprea1_162188
• CHEMBL1591274
• CHEBI:182204
• HMS1548B13
• AKOS024322663
• NCGC00161931-01
• 4-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• PD027851
• 10-HO-5-(4-HO-3,5-DI-MEO-PH)-5AH-FURO(3',4':6,7)NAPHTHO(2,3-D)(1,3)DIOXOL-6-ONE
• 10-Hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
• 4-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzouro[5,6-][1,3]benzodioxol-8-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9609	96.09%
Caco-2	+	0.5725	57.25%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7984	79.84%
OATP2B1 inhibitior	-	0.8642	86.42%
OATP1B1 inhibitior	+	0.8672	86.72%
OATP1B3 inhibitior	+	0.9535	95.35%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7485	74.85%
P-glycoprotein inhibitior	-	0.6628	66.28%
P-glycoprotein substrate	-	0.6327	63.27%
CYP3A4 substrate	+	0.6126	61.26%
CYP2C9 substrate	+	0.5918	59.18%
CYP2D6 substrate	-	0.7535	75.35%
CYP3A4 inhibition	+	0.7847	78.47%
CYP2C9 inhibition	+	0.9212	92.12%
CYP2C19 inhibition	+	0.8883	88.83%
CYP2D6 inhibition	-	0.7327	73.27%
CYP1A2 inhibition	-	0.8453	84.53%
CYP2C8 inhibition	+	0.4713	47.13%
CYP inhibitory promiscuity	+	0.8456	84.56%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4633	46.33%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.8555	85.55%
Skin irritation	-	0.7949	79.49%
Skin corrosion	-	0.9555	95.55%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6658	66.58%
Micronuclear	+	0.8674	86.74%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8235	82.35%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.7718	77.18%
Acute Oral Toxicity (c)	III	0.6411	64.11%
Estrogen receptor binding	+	0.8881	88.81%
Androgen receptor binding	+	0.7132	71.32%
Thyroid receptor binding	+	0.7630	76.30%
Glucocorticoid receptor binding	+	0.8771	87.71%
Aromatase binding	-	0.6971	69.71%
PPAR gamma	+	0.7098	70.98%
Honey bee toxicity	-	0.7460	74.60%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9600	96.00%

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	99.33%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.05%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.50%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.00%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.75%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.75%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.75%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.88%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.28%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.73%	95.89%
CHEMBL2535	P11166	Glucose transporter	85.18%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.51%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.12%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.76%	96.77%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.41%	90.71%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	80.51%	96.86%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.33%	100.00%

Plants that contains it

• Eriope latifolia
• Linum capitatum
• Linum cariense
• Podophyllum peltatum
• Podophyllum versipelle

Cross-Links

• PubChem: 500180
• LOTUS: LTS0123569
• wikiData: Q105127355