7-[(2S,3S,4S,5R,6S)-3-[(2S,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-methoxy-3-(4-methoxyphenyl)chromen-4-one

Details

• Internal ID: c2ad7e8c-33c9-4b94-a506-5d5e1f0d769f
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 7-[(2S,3S,4S,5R,6S)-3-[(2S,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-methoxy-3-(4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2=COC3=CC(=C(C=C3C2=O)OC)OC4C(C(C(C(O4)CO)O)O)OC5C(C(CO5)(CO)O)O
• SMILES (Isomeric): COC1=CC=C(C=C1)C2=COC3=CC(=C(C=C3C2=O)OC)O[C@H]4[C@H]([C@H]([C@H]([C@@H](O4)CO)O)O)O[C@H]5[C@H]([C@@](CO5)(CO)O)O
• InChI: InChI=1S/C28H32O14/c1-36-14-5-3-13(4-6-14)16-10-38-17-8-19(18(37-2)7-15(17)21(16)31)40-26-24(23(33)22(32)20(9-29)41-26)42-27-25(34)28(35,11-30)12-39-27/h3-8,10,20,22-27,29-30,32-35H,9,11-12H2,1-2H3/t20-,22-,23-,24-,25+,26+,27-,28-/m0/s1
• InChI Key: VVSQZIYHJQSIII-JRRIJNMMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₄
• Molecular Weight: 592.50 g/mol
• Exact Mass: 592.17920569 g/mol
• Topological Polar Surface Area (TPSA): 203.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.88
• H-Bond Acceptor: 14
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6634	66.34%
Caco-2	-	0.8775	87.75%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6223	62.23%
OATP2B1 inhibitior	-	0.8494	84.94%
OATP1B1 inhibitior	+	0.9069	90.69%
OATP1B3 inhibitior	+	0.9601	96.01%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8715	87.15%
P-glycoprotein inhibitior	-	0.4398	43.98%
P-glycoprotein substrate	-	0.5254	52.54%
CYP3A4 substrate	+	0.6997	69.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8359	83.59%
CYP3A4 inhibition	-	0.8178	81.78%
CYP2C9 inhibition	-	0.9078	90.78%
CYP2C19 inhibition	-	0.8665	86.65%
CYP2D6 inhibition	-	0.9193	91.93%
CYP1A2 inhibition	-	0.8977	89.77%
CYP2C8 inhibition	+	0.5676	56.76%
CYP inhibitory promiscuity	-	0.7651	76.51%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5686	56.86%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9375	93.75%
Skin irritation	-	0.8182	81.82%
Skin corrosion	-	0.9454	94.54%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6859	68.59%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	+	0.5149	51.49%
skin sensitisation	-	0.8795	87.95%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7777	77.77%
Acute Oral Toxicity (c)	III	0.6977	69.77%
Estrogen receptor binding	+	0.8436	84.36%
Androgen receptor binding	+	0.7273	72.73%
Thyroid receptor binding	+	0.5902	59.02%
Glucocorticoid receptor binding	+	0.6902	69.02%
Aromatase binding	+	0.6393	63.93%
PPAR gamma	+	0.7782	77.82%
Honey bee toxicity	-	0.7472	74.72%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.7109	71.09%

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	99.07%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.60%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.24%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.99%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.74%	89.00%
CHEMBL4302	P08183	P-glycoprotein 1	95.69%	92.98%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.24%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.87%	86.92%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.05%	92.94%
CHEMBL1937	Q92769	Histone deacetylase 2	90.79%	94.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.67%	96.00%
CHEMBL226	P30542	Adenosine A1 receptor	90.57%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.63%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.62%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.41%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.45%	96.77%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.04%	97.36%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.03%	97.14%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.16%	97.28%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.62%	95.83%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	84.49%	95.53%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.27%	94.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.25%	96.21%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.64%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.60%	99.23%
CHEMBL5747	Q92793	CREB-binding protein	82.57%	95.12%
CHEMBL3085	P43003	Excitatory amino acid transporter 1	82.31%	94.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.18%	99.17%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	80.79%	90.95%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	80.13%	96.47%

Plants that contains it

• Centrosema pubescens

Cross-Links

• PubChem: 163078833
• LOTUS: LTS0209216
• wikiData: Q105297856