irilone-4'-O-[beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside]

Details

• Internal ID: aaef2302-609c-4f01-be78-c2fc2f3d6766
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 9-hydroxy-7-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyphenyl]-[1,3]dioxolo[4,5-g]chromen-8-one
• SMILES (Canonical): C1OC2=C(O1)C(=C3C(=C2)OC=C(C3=O)C4=CC=C(C=C4)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)O)O)O)O
• SMILES (Isomeric): C1OC2=C(O1)C(=C3C(=C2)OC=C(C3=O)C4=CC=C(C=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C28H30O16/c29-6-15-19(31)22(34)24(36)27(43-15)39-8-16-20(32)23(35)25(37)28(44-16)42-11-3-1-10(2-4-11)12-7-38-13-5-14-26(41-9-40-14)21(33)17(13)18(12)30/h1-5,7,15-16,19-20,22-25,27-29,31-37H,6,8-9H2/t15-,16-,19-,20-,22+,23+,24-,25-,27-,28-/m1/s1
• InChI Key: MRXZOZKDGKQEMG-SKLZQIAYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₀O₁₆
• Molecular Weight: 622.50 g/mol
• Exact Mass: 622.15338487 g/mol
• Topological Polar Surface Area (TPSA): 244.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -2.10
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• CHEBI:66084
• Q27134597
• 4-(9-hydroxy-8-oxo-8H-[1,3]dioxolo[4,5-g]chromen-7-yl)phenyl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5949	59.49%
Caco-2	-	0.9111	91.11%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6301	63.01%
OATP2B1 inhibitior	-	0.8456	84.56%
OATP1B1 inhibitior	+	0.9292	92.92%
OATP1B3 inhibitior	+	0.9468	94.68%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4657	46.57%
P-glycoprotein inhibitior	-	0.5270	52.70%
P-glycoprotein substrate	-	0.7893	78.93%
CYP3A4 substrate	+	0.6420	64.20%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.5780	57.80%
CYP2C9 inhibition	-	0.8821	88.21%
CYP2C19 inhibition	-	0.7756	77.56%
CYP2D6 inhibition	-	0.8441	84.41%
CYP1A2 inhibition	-	0.8878	88.78%
CYP2C8 inhibition	+	0.5987	59.87%
CYP inhibitory promiscuity	+	0.5366	53.66%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5924	59.24%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9120	91.20%
Skin irritation	-	0.8047	80.47%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3905	39.05%
Micronuclear	+	0.6933	69.33%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8767	87.67%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7380	73.80%
Acute Oral Toxicity (c)	III	0.5647	56.47%
Estrogen receptor binding	+	0.7596	75.96%
Androgen receptor binding	+	0.6342	63.42%
Thyroid receptor binding	-	0.5668	56.68%
Glucocorticoid receptor binding	-	0.5643	56.43%
Aromatase binding	+	0.5635	56.35%
PPAR gamma	+	0.7518	75.18%
Honey bee toxicity	-	0.6995	69.95%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8350	83.50%

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	99.72%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.65%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.51%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.46%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.43%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.36%	96.77%
CHEMBL226	P30542	Adenosine A1 receptor	94.42%	95.93%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.50%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.56%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.50%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.90%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.87%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.55%	92.62%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.28%	96.21%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.52%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.20%	95.56%
CHEMBL4208	P20618	Proteasome component C5	83.46%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.93%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.81%	86.92%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	82.65%	95.53%
CHEMBL3401	O75469	Pregnane X receptor	82.38%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.20%	96.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.87%	97.36%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.66%	95.83%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.42%	100.00%

Plants that contains it

• Iris pseudopumila

Cross-Links

• PubChem: 70697868
• LOTUS: LTS0034656
• wikiData: Q27134597