(1R,5S,6R,8aR)-1-(furan-3-yl)-4-hydroxy-5,8a-dimethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6,7,8-tetrahydro-1H-isochromen-3-one

Details

• Internal ID: 20467942-c1c9-4dfc-9c5a-93e8df375d60
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (1R,5S,6R,8aR)-1-(furan-3-yl)-4-hydroxy-5,8a-dimethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6,7,8-tetrahydro-1H-isochromen-3-one
• SMILES (Canonical): CC1C(CCC2(C1=C(C(=O)OC2C3=COC=C3)O)C)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H](CC[C@@]2(C1=C(C(=O)O[C@H]2C3=COC=C3)O)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C21H28O10/c1-9-11(29-20-17(26)16(25)14(23)12(7-22)30-20)3-5-21(2)13(9)15(24)19(27)31-18(21)10-4-6-28-8-10/h4,6,8-9,11-12,14,16-18,20,22-26H,3,5,7H2,1-2H3/t9-,11-,12-,14-,16+,17-,18+,20-,21-/m1/s1
• InChI Key: XAOOOVFRRCYNSK-ONSJZDGLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₁₀
• Molecular Weight: 440.40 g/mol
• Exact Mass: 440.16824709 g/mol
• Topological Polar Surface Area (TPSA): 159.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.31
• H-Bond Acceptor: 10
• 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	+	0.8915	89.15%
Caco-2	-	0.8088	80.88%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8288	82.88%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	-	0.3365	33.65%
OATP1B3 inhibitior	+	0.8654	86.54%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7154	71.54%
P-glycoprotein inhibitior	-	0.7147	71.47%
P-glycoprotein substrate	-	0.8002	80.02%
CYP3A4 substrate	+	0.6623	66.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8800	88.00%
CYP3A4 inhibition	-	0.7385	73.85%
CYP2C9 inhibition	-	0.8125	81.25%
CYP2C19 inhibition	-	0.8773	87.73%
CYP2D6 inhibition	-	0.8969	89.69%
CYP1A2 inhibition	-	0.7946	79.46%
CYP2C8 inhibition	+	0.4688	46.88%
CYP inhibitory promiscuity	-	0.5988	59.88%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5571	55.71%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9804	98.04%
Skin irritation	-	0.6295	62.95%
Skin corrosion	-	0.9282	92.82%
Ames mutagenesis	-	0.7340	73.40%
Human Ether-a-go-go-Related Gene inhibition	-	0.5421	54.21%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.6423	64.23%
skin sensitisation	-	0.8902	89.02%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6244	62.44%
Acute Oral Toxicity (c)	I	0.5489	54.89%
Estrogen receptor binding	+	0.7999	79.99%
Androgen receptor binding	+	0.5198	51.98%
Thyroid receptor binding	+	0.5619	56.19%
Glucocorticoid receptor binding	+	0.7136	71.36%
Aromatase binding	+	0.6778	67.78%
PPAR gamma	+	0.7484	74.84%
Honey bee toxicity	-	0.8115	81.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5850	58.50%
Fish aquatic toxicity	+	0.9546	95.46%

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	99.61%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.08%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.15%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.27%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.47%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.81%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.54%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.48%	94.00%
CHEMBL221	P23219	Cyclooxygenase-1	86.19%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.09%	95.89%
CHEMBL2581	P07339	Cathepsin D	85.91%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.33%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	84.44%	83.82%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.18%	95.83%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.83%	97.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.76%	91.24%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.92%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.82%	96.00%

Plants that contains it

• Dictamnus dasycarpus

Cross-Links

• PubChem: 161657597
• LOTUS: LTS0147742
• wikiData: Q105324029