Amurenoside A

Details

• Internal ID: 566eed6e-100a-4ab3-9e0a-f7cbc91765d6
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2R,3R,4R,5S,6S)-2-[[(2R,3R,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methoxy]-3,5-dihydroxy-6-methyloxan-4-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)COC6C(C(C(C(O6)C)O)OC(=O)C=CC7=CC(=C(C=C7)O)OC)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H]([C@H](O[C@H]2OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)CO[C@H]6[C@@H]([C@@H]([C@H]([C@@H](O6)C)O)OC(=O)/C=C/C7=CC(=C(C=C7)O)OC)O)O)O)O)O)O
• InChI: InChI=1S/C43H48O23/c1-15-29(50)33(54)35(56)42(61-15)66-40-34(55)31(52)26(14-59-41-36(57)38(30(51)16(2)60-41)64-27(49)9-5-17-4-7-21(46)24(10-17)58-3)63-43(40)65-39-32(53)28-23(48)12-19(44)13-25(28)62-37(39)18-6-8-20(45)22(47)11-18/h4-13,15-16,26,29-31,33-36,38,40-48,50-52,54-57H,14H2,1-3H3/b9-5+/t15-,16-,26+,29-,30-,31-,33+,34-,35+,36+,38+,40+,41+,42-,43-/m0/s1
• InChI Key: MJIKFVGKCRVQNL-WQKFSZIYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₄₈O₂₃
• Molecular Weight: 932.80 g/mol
• Exact Mass: 932.25863777 g/mol
• Topological Polar Surface Area (TPSA): 360.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.86
• H-Bond Acceptor: 23
• H-Bond Donor: 12
• Rotatable Bonds: 12

Synonyms

• [(2R,3R,4R,5S,6S)-2-[[(2R,3R,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methoxy]-3,5-dihydroxy-6-methyloxan-4-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5530	55.30%
Caco-2	-	0.8785	87.85%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5729	57.29%
OATP2B1 inhibitior	-	0.7120	71.20%
OATP1B1 inhibitior	+	0.8694	86.94%
OATP1B3 inhibitior	+	0.9478	94.78%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7837	78.37%
P-glycoprotein inhibitior	+	0.6978	69.78%
P-glycoprotein substrate	+	0.7265	72.65%
CYP3A4 substrate	+	0.7123	71.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8699	86.99%
CYP3A4 inhibition	-	0.9007	90.07%
CYP2C9 inhibition	-	0.8872	88.72%
CYP2C19 inhibition	-	0.9236	92.36%
CYP2D6 inhibition	-	0.9301	93.01%
CYP1A2 inhibition	-	0.9344	93.44%
CYP2C8 inhibition	+	0.9026	90.26%
CYP inhibitory promiscuity	-	0.7459	74.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6348	63.48%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9047	90.47%
Skin irritation	-	0.8375	83.75%
Skin corrosion	-	0.9543	95.43%
Ames mutagenesis	-	0.6265	62.65%
Human Ether-a-go-go-Related Gene inhibition	+	0.7325	73.25%
Micronuclear	+	0.7092	70.92%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.9161	91.61%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.9847	98.47%
Acute Oral Toxicity (c)	III	0.5848	58.48%
Estrogen receptor binding	+	0.7917	79.17%
Androgen receptor binding	+	0.6233	62.33%
Thyroid receptor binding	+	0.5472	54.72%
Glucocorticoid receptor binding	+	0.6892	68.92%
Aromatase binding	+	0.6091	60.91%
PPAR gamma	+	0.7513	75.13%
Honey bee toxicity	-	0.6572	65.72%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9530	95.30%

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	99.89%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	99.24%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	99.05%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	98.92%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.89%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.35%	96.09%
CHEMBL3194	P02766	Transthyretin	95.30%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.40%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.36%	99.17%
CHEMBL2581	P07339	Cathepsin D	93.02%	98.95%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.91%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	90.30%	94.73%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	89.93%	80.78%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.16%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.74%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.56%	94.00%
CHEMBL4208	P20618	Proteasome component C5	83.68%	90.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.52%	95.64%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.85%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.88%	95.50%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.40%	95.78%

Plants that contains it

• Albizia altissima
• Artocarpus altilis
• Centaurea solstitialis
• Cosmos diversifolius
• Cryptocarya oblata
• Curcuma caesia
• Erythrina pallida
• Eucalyptus radiata subsp. radiata
• Inga velutina
• Lactuca serriola
• Lagochilus leiacanthus
• Ocimum africanum
• Onobrychis viciifolia
• Phelline lucida
• Piptostigma fugax
• Rhododendron mucronatum
• Strychnos tricalysioides
• Trichodesma incanum
• Urochloa eminii
• Vicia amurensis
• Xanthorrhoea resinosa

Cross-Links

• PubChem: 10653411
• NPASS: NPC32940
• LOTUS: LTS0256169
• wikiData: Q105165443