[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[3-hydroxy-2-[3-(4-hydroxyphenyl)propanoyl]-5-methoxyphenoxy]-6-(hydroxymethyl)oxan-3-yl] acetate

Details

• Internal ID: 2f7f78db-ef55-4bf8-bbf9-dbe5e5cb417d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[3-hydroxy-2-[3-(4-hydroxyphenyl)propanoyl]-5-methoxyphenoxy]-6-(hydroxymethyl)oxan-3-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(C(C(OC1OC2=CC(=CC(=C2C(=O)CCC3=CC=C(C=C3)O)O)OC)CO)O)O
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=CC(=CC(=C2C(=O)CCC3=CC=C(C=C3)O)O)OC)CO)O)O
• InChI: InChI=1S/C24H28O11/c1-12(26)33-23-22(31)21(30)19(11-25)35-24(23)34-18-10-15(32-2)9-17(29)20(18)16(28)8-5-13-3-6-14(27)7-4-13/h3-4,6-7,9-10,19,21-25,27,29-31H,5,8,11H2,1-2H3/t19-,21-,22+,23-,24-/m1/s1
• InChI Key: MLDPUOQFWOXHRX-PFKOEMKTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₁₁
• Molecular Weight: 492.50 g/mol
• Exact Mass: 492.16316171 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 0.67
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8194	81.94%
Caco-2	-	0.8389	83.89%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7398	73.98%
OATP2B1 inhibitior	-	0.8490	84.90%
OATP1B1 inhibitior	+	0.8484	84.84%
OATP1B3 inhibitior	+	0.9297	92.97%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.9302	93.02%
P-glycoprotein inhibitior	+	0.6111	61.11%
P-glycoprotein substrate	-	0.6436	64.36%
CYP3A4 substrate	+	0.6141	61.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8675	86.75%
CYP3A4 inhibition	-	0.8270	82.70%
CYP2C9 inhibition	-	0.6187	61.87%
CYP2C19 inhibition	-	0.8464	84.64%
CYP2D6 inhibition	-	0.9273	92.73%
CYP1A2 inhibition	-	0.8101	81.01%
CYP2C8 inhibition	+	0.6555	65.55%
CYP inhibitory promiscuity	-	0.8730	87.30%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.8006	80.06%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9152	91.52%
Skin irritation	-	0.8557	85.57%
Skin corrosion	-	0.9512	95.12%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5297	52.97%
Micronuclear	-	0.6167	61.67%
Hepatotoxicity	-	0.7051	70.51%
skin sensitisation	-	0.9149	91.49%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8339	83.39%
Acute Oral Toxicity (c)	III	0.7863	78.63%
Estrogen receptor binding	+	0.8029	80.29%
Androgen receptor binding	+	0.5865	58.65%
Thyroid receptor binding	-	0.5264	52.64%
Glucocorticoid receptor binding	+	0.6418	64.18%
Aromatase binding	-	0.5386	53.86%
PPAR gamma	+	0.7411	74.11%
Honey bee toxicity	-	0.7491	74.91%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6255	62.55%
Fish aquatic toxicity	+	0.6954	69.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.75%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.45%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.35%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.37%	99.17%
CHEMBL2581	P07339	Cathepsin D	94.05%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.62%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	92.27%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.55%	95.89%
CHEMBL4208	P20618	Proteasome component C5	90.49%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.19%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.96%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.38%	95.56%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	86.08%	85.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.84%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.80%	96.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.27%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.49%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.56%	89.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.33%	97.21%

Plants that contains it

• Pieris japonica
• Psorospermum adamauense
• Psorospermum glaberrimum
• Psorospermum tenuifolium

Cross-Links

• PubChem: 11431848
• LOTUS: LTS0149120
• wikiData: Q104991203