(3R,3aR,6R,6aR)-3,6a-dihydroxy-6-[(4-hydroxyphenyl)methyl]-6-methoxy-3,3a-dihydro-2H-furo[3,2-b]furan-5-one

Details

• Internal ID: 72d37a90-c66f-413f-b0ba-a969409cca5a
• Taxonomy: Organoheterocyclic compounds > Furofurans > Isosorbides
• IUPAC Name: (3R,3aR,6R,6aR)-3,6a-dihydroxy-6-[(4-hydroxyphenyl)methyl]-6-methoxy-3,3a-dihydro-2H-furo[3,2-b]furan-5-one
• SMILES (Canonical): COC1(C(=O)OC2C1(OCC2O)O)CC3=CC=C(C=C3)O
• SMILES (Isomeric): CO[C@]1(C(=O)O[C@H]2[C@]1(OC[C@H]2O)O)CC3=CC=C(C=C3)O
• InChI: InChI=1S/C14H16O7/c1-19-13(6-8-2-4-9(15)5-3-8)12(17)21-11-10(16)7-20-14(11,13)18/h2-5,10-11,15-16,18H,6-7H2,1H3/t10-,11-,13+,14-/m1/s1
• InChI Key: LHVOCXKOGQTWPH-MHDGFBEUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₆O₇
• Molecular Weight: 296.27 g/mol
• Exact Mass: 296.08960285 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.68
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9455	94.55%
Caco-2	-	0.6767	67.67%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6704	67.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9007	90.07%
OATP1B3 inhibitior	+	0.9294	92.94%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7850	78.50%
P-glycoprotein inhibitior	-	0.9230	92.30%
P-glycoprotein substrate	-	0.6128	61.28%
CYP3A4 substrate	+	0.6151	61.51%
CYP2C9 substrate	-	0.8016	80.16%
CYP2D6 substrate	-	0.8035	80.35%
CYP3A4 inhibition	-	0.9077	90.77%
CYP2C9 inhibition	-	0.9054	90.54%
CYP2C19 inhibition	-	0.9011	90.11%
CYP2D6 inhibition	-	0.9223	92.23%
CYP1A2 inhibition	-	0.8744	87.44%
CYP2C8 inhibition	-	0.7063	70.63%
CYP inhibitory promiscuity	-	0.8818	88.18%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5434	54.34%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.8294	82.94%
Skin irritation	-	0.7383	73.83%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8151	81.51%
Micronuclear	-	0.6267	62.67%
Hepatotoxicity	-	0.5354	53.54%
skin sensitisation	-	0.8273	82.73%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.4575	45.75%
Acute Oral Toxicity (c)	III	0.5270	52.70%
Estrogen receptor binding	+	0.6045	60.45%
Androgen receptor binding	+	0.6838	68.38%
Thyroid receptor binding	-	0.6360	63.60%
Glucocorticoid receptor binding	-	0.5066	50.66%
Aromatase binding	-	0.6123	61.23%
PPAR gamma	-	0.5131	51.31%
Honey bee toxicity	-	0.8257	82.57%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.7660	76.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.46%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.59%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.54%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.49%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.56%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.71%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.29%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.76%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.20%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.96%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.77%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.81%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.28%	95.89%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162933529
• LOTUS: LTS0011043
• wikiData: Q105152004