6''-O-Acetylastragalin

Details

• Internal ID: f7f761aa-0f3b-42ea-87d8-fac1c7328766
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)O)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)O)O)O
• InChI: InChI=1S/C23H22O12/c1-9(24)32-8-15-17(28)19(30)20(31)23(34-15)35-22-18(29)16-13(27)6-12(26)7-14(16)33-21(22)10-2-4-11(25)5-3-10/h2-7,15,17,19-20,23,25-28,30-31H,8H2,1H3/t15-,17-,19+,20-,23+/m1/s1
• InChI Key: AKENCGNASJPQNR-LNNZMUSMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₁₂
• Molecular Weight: 490.40 g/mol
• Exact Mass: 490.11112613 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.33
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• 6-O-Acetylastragalin
• 6''-O-Acetylastragalin
• Kaempferol 3-O-acetyl-glucoside
• [(2R,3S,4S,5R,6S)-6-[5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• Kaempferol 3-O-(6''-O-acetyl)glucoside
• starbld0000800
• 6/'/'-O-Acetylastragalin
• Kaempferol 3-(acetylglucoside)
• MEGxp0_000380
• ACon1_001416
• DTXSID701341626
• AKOS032961780
• Kaempferol-3-O--D-6''-acetylglucoside
• BRD-K18568936-001-01-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5759	57.59%
Caco-2	-	0.9146	91.46%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6926	69.26%
OATP2B1 inhibitior	+	0.7161	71.61%
OATP1B1 inhibitior	+	0.8682	86.82%
OATP1B3 inhibitior	+	0.9515	95.15%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8087	80.87%
P-glycoprotein inhibitior	-	0.4701	47.01%
P-glycoprotein substrate	-	0.6657	66.57%
CYP3A4 substrate	+	0.6453	64.53%
CYP2C9 substrate	+	0.5319	53.19%
CYP2D6 substrate	-	0.8787	87.87%
CYP3A4 inhibition	-	0.9505	95.05%
CYP2C9 inhibition	-	0.9129	91.29%
CYP2C19 inhibition	-	0.9233	92.33%
CYP2D6 inhibition	-	0.9603	96.03%
CYP1A2 inhibition	-	0.8935	89.35%
CYP2C8 inhibition	+	0.8489	84.89%
CYP inhibitory promiscuity	-	0.8491	84.91%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7134	71.34%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.8872	88.72%
Skin irritation	-	0.8133	81.33%
Skin corrosion	-	0.9497	94.97%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4309	43.09%
Micronuclear	+	0.5892	58.92%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.9339	93.39%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7726	77.26%
Acute Oral Toxicity (c)	III	0.5815	58.15%
Estrogen receptor binding	+	0.8035	80.35%
Androgen receptor binding	+	0.7653	76.53%
Thyroid receptor binding	-	0.5719	57.19%
Glucocorticoid receptor binding	+	0.6491	64.91%
Aromatase binding	-	0.5401	54.01%
PPAR gamma	+	0.6074	60.74%
Honey bee toxicity	-	0.8240	82.40%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6650	66.50%
Fish aquatic toxicity	+	0.9613	96.13%

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	98.94%	91.11%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	97.84%	95.64%
CHEMBL2581	P07339	Cathepsin D	97.58%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.32%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.95%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	93.60%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.88%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.65%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.29%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	90.54%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.22%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.16%	99.17%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.84%	95.78%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.65%	94.80%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.59%	99.15%
CHEMBL3194	P02766	Transthyretin	81.30%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.93%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.55%	95.56%

Plants that contains it

• Arnica chamissonis
• Arnica longifolia
• Baphia pubescens
• Chiliadenus montanus
• Crocus sativus
• Lasiosiphon kraussianus
• Morinda morindoides
• Petrosedum pruinatum
• Picea abies
• Populus angustifolia
• Sasa senanensis
• Senecio franchetii
• Stachyurus himalaicus

Cross-Links

• PubChem: 10435673
• NPASS: NPC27641
• LOTUS: LTS0090405
• wikiData: Q105172394