5-hydroxy-3-[4-hydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

• Internal ID: fb5dc98b-7639-4317-b357-dc18548f379e
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 5-hydroxy-3-[4-hydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=COC3=CC(=CC(=C3C2=O)O)OC4C(C(C(C(O4)CO)O)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=COC3=CC(=CC(=C3C2=O)O)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O[C@@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C27H30O16/c28-6-16-20(33)22(35)24(37)26(42-16)40-10-4-13(31)18-15(5-10)39-8-11(19(18)32)9-1-2-12(30)14(3-9)41-27-25(38)23(36)21(34)17(7-29)43-27/h1-5,8,16-17,20-31,33-38H,6-7H2/t16-,17-,20-,21-,22+,23+,24-,25-,26+,27+/m1/s1
• InChI Key: WBUYXWBGDDXLJL-XHYOFSJDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₆
• Molecular Weight: 610.50 g/mol
• Exact Mass: 610.15338487 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -2.77
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9102	91.02%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5514	55.14%
OATP1B1 inhibitior	+	0.9524	95.24%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7273	72.73%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.8722	87.22%
CYP3A4 substrate	+	0.6038	60.38%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9315	93.15%
CYP2C19 inhibition	-	0.9047	90.47%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9180	91.80%
CYP2C8 inhibition	+	0.6656	66.56%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8826	88.26%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.5182	51.82%
Human Ether-a-go-go-Related Gene inhibition	+	0.7020	70.20%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7071	70.71%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.5561	55.61%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.7492	74.92%
Androgen receptor binding	+	0.5523	55.23%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5627	56.27%
Aromatase binding	+	0.5554	55.54%
PPAR gamma	+	0.7907	79.07%
Honey bee toxicity	-	0.7236	72.36%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5299	52.99%
Fish aquatic toxicity	+	0.7958	79.58%

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	98.77%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.51%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.74%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.64%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.41%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.96%	96.21%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	92.85%	95.78%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.55%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.72%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.00%	97.09%
CHEMBL3194	P02766	Transthyretin	87.68%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.35%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.88%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.39%	95.56%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.08%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.21%	95.89%
CHEMBL220	P22303	Acetylcholinesterase	82.14%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.43%	90.71%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.76%	95.53%
CHEMBL4208	P20618	Proteasome component C5	80.52%	90.00%

Plants that contains it

• Perilla frutescens

Cross-Links

• PubChem: 99653118
• NPASS: NPC89845