(3R,3aS,6aS)-3-(4-hydroxy-3-methoxyphenyl)-3,3a,4,6a-tetrahydro-1H-furo[3,4-c]furan-6-one

Details

• Internal ID: 109a6d57-615d-4daf-9aaf-86fe40d11c3e
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones
• IUPAC Name: (3R,3aS,6aS)-3-(4-hydroxy-3-methoxyphenyl)-3,3a,4,6a-tetrahydro-1H-furo[3,4-c]furan-6-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2C3COC(=O)C3CO2)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)[C@H]2[C@@H]3COC(=O)[C@@H]3CO2)O
• InChI: InChI=1S/C13H14O5/c1-16-11-4-7(2-3-10(11)14)12-8-5-18-13(15)9(8)6-17-12/h2-4,8-9,12,14H,5-6H2,1H3/t8-,9-,12+/m1/s1
• InChI Key: HYZRWYQBGNTGTK-LNLATYFQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₄O₅
• Molecular Weight: 250.25 g/mol
• Exact Mass: 250.08412354 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.26
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9904	99.04%
Caco-2	+	0.7942	79.42%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8333	83.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9362	93.62%
OATP1B3 inhibitior	+	0.9764	97.64%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.9129	91.29%
P-glycoprotein inhibitior	-	0.9359	93.59%
P-glycoprotein substrate	-	0.9365	93.65%
CYP3A4 substrate	+	0.5250	52.50%
CYP2C9 substrate	+	0.5918	59.18%
CYP2D6 substrate	-	0.7517	75.17%
CYP3A4 inhibition	-	0.5999	59.99%
CYP2C9 inhibition	+	0.6787	67.87%
CYP2C19 inhibition	+	0.7064	70.64%
CYP2D6 inhibition	-	0.8620	86.20%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	-	0.7019	70.19%
CYP inhibitory promiscuity	-	0.5415	54.15%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9040	90.40%
Carcinogenicity (trinary)	Non-required	0.4930	49.30%
Eye corrosion	-	0.9664	96.64%
Eye irritation	+	0.5564	55.64%
Skin irritation	-	0.7823	78.23%
Skin corrosion	-	0.9710	97.10%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5093	50.93%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	-	0.5906	59.06%
skin sensitisation	-	0.7011	70.11%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7036	70.36%
Acute Oral Toxicity (c)	III	0.6023	60.23%
Estrogen receptor binding	+	0.6207	62.07%
Androgen receptor binding	+	0.6867	68.67%
Thyroid receptor binding	-	0.6582	65.82%
Glucocorticoid receptor binding	-	0.4660	46.60%
Aromatase binding	-	0.7177	71.77%
PPAR gamma	-	0.6856	68.56%
Honey bee toxicity	-	0.8374	83.74%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9438	94.38%

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	98.48%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.56%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.09%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.65%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.34%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.90%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.47%	94.00%
CHEMBL2535	P11166	Glucose transporter	88.25%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.62%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.45%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.10%	97.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.87%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.64%	99.23%

Plants that contains it

• Zanthoxylum simulans

Cross-Links

• PubChem: 162923974
• LOTUS: LTS0090035
• wikiData: Q105035552