(2S)-7-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethyl-2,3-dihydrochromen-4-one

Details

• Internal ID: 4e2479aa-02be-4ea5-b09f-5d72df43ce4f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: (2S)-7-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC1=C(C2=C(C(=C1OC3C(C(C(C(O3)COC4C(C(CO4)(CO)O)O)O)O)O)C)OC(CC2=O)C5=CC=C(C=C5)O)O
• SMILES (Isomeric): CC1=C(C2=C(C(=C1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@](CO4)(CO)O)O)O)O)O)C)O[C@@H](CC2=O)C5=CC=C(C=C5)O)O
• InChI: InChI=1S/C28H34O14/c1-11-19(32)18-15(31)7-16(13-3-5-14(30)6-4-13)40-24(18)12(2)23(11)42-26-22(35)21(34)20(33)17(41-26)8-38-27-25(36)28(37,9-29)10-39-27/h3-6,16-17,20-22,25-27,29-30,32-37H,7-10H2,1-2H3/t16-,17+,20+,21-,22+,25-,26-,27+,28+/m0/s1
• InChI Key: KABGCWRGCBCLOH-YFVJAWDISA-N
• Popularity: 41 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₄O₁₄
• Molecular Weight: 594.60 g/mol
• Exact Mass: 594.19485575 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -0.94
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• AC-20237

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6961	69.61%
Caco-2	-	0.8857	88.57%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7317	73.17%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.8330	83.30%
OATP1B3 inhibitior	+	0.9486	94.86%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4679	46.79%
P-glycoprotein inhibitior	-	0.5118	51.18%
P-glycoprotein substrate	-	0.5642	56.42%
CYP3A4 substrate	+	0.6893	68.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8560	85.60%
CYP3A4 inhibition	-	0.8749	87.49%
CYP2C9 inhibition	-	0.9183	91.83%
CYP2C19 inhibition	-	0.8641	86.41%
CYP2D6 inhibition	-	0.9324	93.24%
CYP1A2 inhibition	-	0.8888	88.88%
CYP2C8 inhibition	+	0.6734	67.34%
CYP inhibitory promiscuity	-	0.8048	80.48%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6108	61.08%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9262	92.62%
Skin irritation	-	0.8232	82.32%
Skin corrosion	-	0.9525	95.25%
Ames mutagenesis	+	0.5446	54.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.3628	36.28%
Micronuclear	+	0.5774	57.74%
Hepatotoxicity	-	0.6499	64.99%
skin sensitisation	-	0.8824	88.24%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.5959	59.59%
Acute Oral Toxicity (c)	III	0.5433	54.33%
Estrogen receptor binding	+	0.8360	83.60%
Androgen receptor binding	+	0.5880	58.80%
Thyroid receptor binding	+	0.5411	54.11%
Glucocorticoid receptor binding	+	0.6548	65.48%
Aromatase binding	+	0.6774	67.74%
PPAR gamma	+	0.7098	70.98%
Honey bee toxicity	-	0.7512	75.12%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5950	59.50%
Fish aquatic toxicity	+	0.8926	89.26%

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	98.93%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.69%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.31%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.34%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.72%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.46%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.79%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.28%	99.23%
CHEMBL226	P30542	Adenosine A1 receptor	85.63%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.02%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.65%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	83.89%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.76%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.00%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.60%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.42%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.15%	99.15%

Plants that contains it

• Artemisia annua
• Rhododendron dauricum
• Rhododendron mucronulatum

Cross-Links

• PubChem: 11093171
• NPASS: NPC210877