(8aR)-2-(3,4-dihydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromene-5,7,8a-triol

Details

• Internal ID: 6878ae0a-10e2-470d-98a4-77d33a743b68
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (8aR)-2-(3,4-dihydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromene-5,7,8a-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4(C=C(C=C(C4=C3)O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(O[C@@]4(C=C(C=C(C4=C3)O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C27H32O16/c1-9-18(32)20(34)22(36)25(40-9)39-8-17-19(33)21(35)23(37)26(42-17)41-16-6-12-14(30)5-11(28)7-27(12,38)43-24(16)10-2-3-13(29)15(31)4-10/h2-7,9,17-23,25-26,28-38H,8H2,1H3/t9-,17+,18-,19+,20+,21-,22+,23+,25+,26+,27+/m0/s1
• InChI Key: IRSGRLMGSFMPBE-DATOARKTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₁₆
• Molecular Weight: 612.50 g/mol
• Exact Mass: 612.16903493 g/mol
• Topological Polar Surface Area (TPSA): 269.00 Ų
• XlogP: -3.20
• Atomic LogP (AlogP): -2.02
• H-Bond Acceptor: 16
• H-Bond Donor: 11
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6799	67.99%
Caco-2	-	0.9022	90.22%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7462	74.62%
OATP2B1 inhibitior	-	0.7116	71.16%
OATP1B1 inhibitior	+	0.9048	90.48%
OATP1B3 inhibitior	+	0.9492	94.92%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7908	79.08%
P-glycoprotein inhibitior	-	0.6088	60.88%
P-glycoprotein substrate	+	0.5097	50.97%
CYP3A4 substrate	+	0.6526	65.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8545	85.45%
CYP3A4 inhibition	-	0.9081	90.81%
CYP2C9 inhibition	-	0.5510	55.10%
CYP2C19 inhibition	-	0.5000	50.00%
CYP2D6 inhibition	-	0.8461	84.61%
CYP1A2 inhibition	-	0.7329	73.29%
CYP2C8 inhibition	+	0.7505	75.05%
CYP inhibitory promiscuity	+	0.6071	60.71%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6021	60.21%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9011	90.11%
Skin irritation	-	0.7694	76.94%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	-	0.5170	51.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7369	73.69%
Micronuclear	+	0.6018	60.18%
Hepatotoxicity	-	0.6841	68.41%
skin sensitisation	-	0.8308	83.08%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.9132	91.32%
Acute Oral Toxicity (c)	III	0.4435	44.35%
Estrogen receptor binding	+	0.7176	71.76%
Androgen receptor binding	+	0.5242	52.42%
Thyroid receptor binding	+	0.5787	57.87%
Glucocorticoid receptor binding	+	0.5462	54.62%
Aromatase binding	+	0.6449	64.49%
PPAR gamma	+	0.7067	70.67%
Honey bee toxicity	-	0.7067	70.67%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5550	55.50%
Fish aquatic toxicity	+	0.9256	92.56%

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%
CHEMBL2581	P07339	Cathepsin D	95.78%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.50%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	94.51%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.36%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.93%	99.15%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.93%	97.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.68%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.13%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	89.64%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	89.41%	94.73%
CHEMBL4208	P20618	Proteasome component C5	86.88%	90.00%
CHEMBL221	P23219	Cyclooxygenase-1	84.49%	90.17%
CHEMBL1944	P08473	Neprilysin	84.20%	92.63%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.88%	95.64%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.28%	92.94%
CHEMBL3492	P49721	Proteasome Macropain subunit	83.06%	90.24%
CHEMBL1937	Q92769	Histone deacetylase 2	81.75%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.60%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.56%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.83%	95.89%

Plants that contains it

• Hedera colchica

Cross-Links

• PubChem: 163019469
• LOTUS: LTS0160371
• wikiData: Q105119096