(3S,3aR,4'R,6R,6aR)-3-hydroxy-4'-(4-hydroxyphenyl)-6a-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,3a-dihydro-2H-furo[3,2-b]furan-6,5'-oxolane]-2',5-dione

Details

• Internal ID: 1d7b20a2-9ad9-4b6b-bbaf-cd2909135123
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (3S,3aR,4'R,6R,6aR)-3-hydroxy-4'-(4-hydroxyphenyl)-6a-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,3a-dihydro-2H-furo[3,2-b]furan-6,5'-oxolane]-2',5-dione
• SMILES (Canonical): C1C(C2(C(=O)OC3C2(OCC3O)OC4C(C(C(C(O4)CO)O)O)O)OC1=O)C5=CC=C(C=C5)O
• SMILES (Isomeric): C1[C@@H]([C@@]2(C(=O)O[C@H]3[C@@]2(OC[C@@H]3O)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC1=O)C5=CC=C(C=C5)O
• InChI: InChI=1S/C21H24O13/c22-6-12-14(26)15(27)16(28)18(31-12)34-21-17(11(24)7-30-21)32-19(29)20(21)10(5-13(25)33-20)8-1-3-9(23)4-2-8/h1-4,10-12,14-18,22-24,26-28H,5-7H2/t10-,11+,12-,14-,15+,16-,17-,18-,20+,21-/m1/s1
• InChI Key: LQPXLFOWOYAKCV-ZKLKCDADSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₁₃
• Molecular Weight: 484.40 g/mol
• Exact Mass: 484.12169082 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -3.01
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4768	47.68%
Caco-2	-	0.8959	89.59%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6147	61.47%
OATP2B1 inhibitior	-	0.8541	85.41%
OATP1B1 inhibitior	+	0.8464	84.64%
OATP1B3 inhibitior	+	0.9634	96.34%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6422	64.22%
P-glycoprotein inhibitior	-	0.6922	69.22%
P-glycoprotein substrate	-	0.7022	70.22%
CYP3A4 substrate	+	0.6419	64.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8493	84.93%
CYP3A4 inhibition	-	0.8514	85.14%
CYP2C9 inhibition	-	0.9264	92.64%
CYP2C19 inhibition	-	0.8781	87.81%
CYP2D6 inhibition	-	0.9258	92.58%
CYP1A2 inhibition	-	0.9359	93.59%
CYP2C8 inhibition	+	0.4528	45.28%
CYP inhibitory promiscuity	-	0.8787	87.87%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5357	53.57%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9434	94.34%
Skin irritation	-	0.8102	81.02%
Skin corrosion	-	0.9458	94.58%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5628	56.28%
Micronuclear	+	0.5633	56.33%
Hepatotoxicity	-	0.7343	73.43%
skin sensitisation	-	0.8836	88.36%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.4869	48.69%
Acute Oral Toxicity (c)	III	0.5556	55.56%
Estrogen receptor binding	+	0.7329	73.29%
Androgen receptor binding	+	0.6975	69.75%
Thyroid receptor binding	-	0.5772	57.72%
Glucocorticoid receptor binding	-	0.4848	48.48%
Aromatase binding	+	0.6375	63.75%
PPAR gamma	+	0.6350	63.50%
Honey bee toxicity	-	0.7092	70.92%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5550	55.50%
Fish aquatic toxicity	+	0.6494	64.94%

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	99.63%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.98%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	95.10%	83.82%
CHEMBL1951	P21397	Monoamine oxidase A	93.57%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.33%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.30%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.14%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.86%	96.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.07%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.25%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.12%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.10%	86.92%
CHEMBL2581	P07339	Cathepsin D	84.56%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.50%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.83%	99.23%
CHEMBL4208	P20618	Proteasome component C5	81.08%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	80.79%	94.73%

Plants that contains it

• Viburnum wrightii

Cross-Links

• PubChem: 162850294
• LOTUS: LTS0231045
• wikiData: Q105155665