[(2S,3S,4R,5R,6R)-3,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-4-yl] (2S)-2-methylbutanoate

Details

• Internal ID: e97b0395-dafb-45e2-9131-121c4ae24eb5
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: [(2S,3S,4R,5R,6R)-3,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-4-yl] (2S)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C(C(OC(C1O)C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=C(C=C4)O)O)OC)CO)O
• SMILES (Isomeric): CC[C@H](C)C(=O)O[C@H]1[C@@H]([C@H](O[C@H]([C@@H]1O)C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=C(C=C4)O)O)OC)CO)O
• InChI: InChI=1S/C27H30O11/c1-4-12(2)27(34)38-26-22(32)19(11-28)37-25(23(26)33)21-18(35-3)10-16(31)20-15(30)9-17(36-24(20)21)13-5-7-14(29)8-6-13/h5-10,12,19,22-23,25-26,28-29,31-33H,4,11H2,1-3H3/t12-,19+,22+,23-,25-,26-/m0/s1
• InChI Key: OHXSEHQAFDYWTK-PNUZGILLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₁
• Molecular Weight: 530.50 g/mol
• Exact Mass: 530.17881177 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 1.99
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8515	85.15%
Caco-2	-	0.8377	83.77%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6037	60.37%
OATP2B1 inhibitior	-	0.8437	84.37%
OATP1B1 inhibitior	+	0.8021	80.21%
OATP1B3 inhibitior	+	0.8160	81.60%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9528	95.28%
P-glycoprotein inhibitior	-	0.4482	44.82%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6503	65.03%
CYP2C9 substrate	+	0.6327	63.27%
CYP2D6 substrate	-	0.8510	85.10%
CYP3A4 inhibition	-	0.9081	90.81%
CYP2C9 inhibition	-	0.7604	76.04%
CYP2C19 inhibition	-	0.8788	87.88%
CYP2D6 inhibition	-	0.9644	96.44%
CYP1A2 inhibition	-	0.8781	87.81%
CYP2C8 inhibition	+	0.7289	72.89%
CYP inhibitory promiscuity	-	0.7847	78.47%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6865	68.65%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9275	92.75%
Skin irritation	-	0.8587	85.87%
Skin corrosion	-	0.9594	95.94%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5162	51.62%
Micronuclear	+	0.5874	58.74%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.9143	91.43%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.7745	77.45%
Acute Oral Toxicity (c)	III	0.6589	65.89%
Estrogen receptor binding	+	0.8003	80.03%
Androgen receptor binding	+	0.7926	79.26%
Thyroid receptor binding	+	0.5478	54.78%
Glucocorticoid receptor binding	+	0.7504	75.04%
Aromatase binding	-	0.4930	49.30%
PPAR gamma	+	0.6501	65.01%
Honey bee toxicity	-	0.7004	70.04%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6949	69.49%
Fish aquatic toxicity	+	0.9073	90.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.76%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.52%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.83%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.84%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.43%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.72%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.52%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.49%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.31%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.68%	86.92%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.34%	96.21%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.49%	99.15%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.40%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.14%	97.14%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	86.72%	89.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.55%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.23%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.54%	92.62%
CHEMBL3401	O75469	Pregnane X receptor	82.41%	94.73%

Plants that contains it

• Trollius ledebourii

Cross-Links

• PubChem: 162961442
• LOTUS: LTS0162741
• wikiData: Q105192363