Astragaloside

Details

• Internal ID: 911e25e2-c9c2-4ee3-9498-958a014b45c5
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)COC5C(C(C(C(O5)CO)O)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C28H32O17/c1-40-13-4-9(2-3-11(13)31)25-26(20(35)17-12(32)5-10(30)6-14(17)42-25)45-28-24(39)22(37)19(34)16(44-28)8-41-27-23(38)21(36)18(33)15(7-29)43-27/h2-6,15-16,18-19,21-24,27-34,36-39H,7-8H2,1H3/t15-,16-,18-,19-,21+,22+,23-,24-,27-,28+/m1/s1
• InChI Key: GPZLFWVUSQREQH-QDYVESOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₇
• Molecular Weight: 640.50 g/mol
• Exact Mass: 640.16394955 g/mol
• Topological Polar Surface Area (TPSA): 275.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -2.41
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

• 17429-69-5
• Isorhamnetin 3-gentiobioside
• 5X4V9DGC6L
• 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• 4H-1-Benzopyran-4-one, 3-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-
• 4H-1-Benzopyran-4-one, 3-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-
• UNII-5X4V9DGC6L
• Isorhamnetin 3-O-gentiobioside
• DTXSID30169811
• HY-N0435
• AKOS015903992
• 5,7-dihydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
• AC-34281
• AS-75698
• CS-0008954
• A811629
• Isorhamnetin 3-O-(beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside)
• 3-[(6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one
• 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5457	54.57%
Caco-2	-	0.9260	92.60%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5961	59.61%
OATP2B1 inhibitior	-	0.5746	57.46%
OATP1B1 inhibitior	+	0.8997	89.97%
OATP1B3 inhibitior	+	0.9786	97.86%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4865	48.65%
P-glycoprotein inhibitior	-	0.5349	53.49%
P-glycoprotein substrate	-	0.5528	55.28%
CYP3A4 substrate	+	0.6446	64.46%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9437	94.37%
CYP2C9 inhibition	-	0.9060	90.60%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.9150	91.50%
CYP2C8 inhibition	+	0.8645	86.45%
CYP inhibitory promiscuity	-	0.7142	71.42%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6642	66.42%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9097	90.97%
Skin irritation	-	0.8320	83.20%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	-	0.5828	58.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.4451	44.51%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7533	75.33%
Acute Oral Toxicity (c)	III	0.6678	66.78%
Estrogen receptor binding	+	0.8526	85.26%
Androgen receptor binding	+	0.5821	58.21%
Thyroid receptor binding	-	0.4933	49.33%
Glucocorticoid receptor binding	+	0.5923	59.23%
Aromatase binding	+	0.6256	62.56%
PPAR gamma	+	0.7537	75.37%
Honey bee toxicity	-	0.7728	77.28%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6149	61.49%
Fish aquatic toxicity	+	0.6698	66.98%

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	99.15%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.35%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.33%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.57%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.35%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.06%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.46%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.07%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.77%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	88.99%	94.73%
CHEMBL220	P22303	Acetylcholinesterase	88.10%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.89%	86.92%
CHEMBL3194	P02766	Transthyretin	86.80%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.45%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.07%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.60%	96.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.22%	95.78%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	81.56%	95.64%

Plants that contains it

• Allium neapolitanum
• Astragalus aegobromus
• Astragalus buchtormensis
• Astragalus exscapus
• Senna alexandrina
• Tribulus terrestris

Cross-Links

• PubChem: 5488387
• LOTUS: LTS0017885
• wikiData: Q72444003