(3aS,6R,7aR)-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,6,7,7a-tetrahydro-3H-1-benzofuran-2-one

Details

• Internal ID: c2c2fd85-8381-4d01-ab2d-3762d4a6a43a
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (3aS,6R,7aR)-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,6,7,7a-tetrahydro-3H-1-benzofuran-2-one
• SMILES (Canonical): C1C(C=CC2C1OC(=O)C2)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C1[C@H](C=C[C@H]2[C@@H]1OC(=O)C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C14H20O8/c15-5-9-11(17)12(18)13(19)14(22-9)20-7-2-1-6-3-10(16)21-8(6)4-7/h1-2,6-9,11-15,17-19H,3-5H2/t6-,7+,8-,9-,11-,12+,13-,14-/m1/s1
• InChI Key: XKKLQZHEFFXJAK-KNOPZTTJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₀O₈
• Molecular Weight: 316.30 g/mol
• Exact Mass: 316.11581759 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.94
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5496	54.96%
Caco-2	-	0.8629	86.29%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7359	73.59%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.8634	86.34%
OATP1B3 inhibitior	+	0.9605	96.05%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9177	91.77%
P-glycoprotein inhibitior	-	0.9393	93.93%
P-glycoprotein substrate	-	0.9445	94.45%
CYP3A4 substrate	+	0.5256	52.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8731	87.31%
CYP3A4 inhibition	-	0.9066	90.66%
CYP2C9 inhibition	-	0.9459	94.59%
CYP2C19 inhibition	-	0.8672	86.72%
CYP2D6 inhibition	-	0.8974	89.74%
CYP1A2 inhibition	-	0.9043	90.43%
CYP2C8 inhibition	-	0.8380	83.80%
CYP inhibitory promiscuity	-	0.8292	82.92%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6993	69.93%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9416	94.16%
Skin irritation	-	0.8269	82.69%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5726	57.26%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7071	70.71%
skin sensitisation	-	0.8945	89.45%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.6182	61.82%
Acute Oral Toxicity (c)	III	0.4139	41.39%
Estrogen receptor binding	-	0.6099	60.99%
Androgen receptor binding	-	0.6497	64.97%
Thyroid receptor binding	-	0.6110	61.10%
Glucocorticoid receptor binding	-	0.5189	51.89%
Aromatase binding	+	0.6346	63.46%
PPAR gamma	-	0.5276	52.76%
Honey bee toxicity	-	0.7807	78.07%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8247	82.47%

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	95.48%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.74%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.90%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.64%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.94%	95.56%
CHEMBL2581	P07339	Cathepsin D	84.47%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.96%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.26%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.11%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	80.71%	94.73%

Plants that contains it

• Glochidion zeylanicum

Cross-Links

• PubChem: 10829178
• LOTUS: LTS0042023
• wikiData: Q105329524