Amurenoside B

Details

• Internal ID: e855377e-141b-475f-9bd5-4df1d0715269
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2R,3R,4R,5R,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]-4,5-dihydroxy-6-methyloxan-3-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)O)OC(=O)C=CC7=CC(=C(C=C7)O)OC)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)O)OC(=O)/C=C/C7=CC(=C(C=C7)O)OC)O)O)O)O)O
• InChI: InChI=1S/C43H48O23/c1-15-29(50)33(54)36(57)41(60-15)66-40-35(56)31(52)26(14-59-42-39(34(55)30(51)16(2)61-42)64-27(49)9-5-17-4-7-21(46)24(10-17)58-3)63-43(40)65-38-32(53)28-23(48)12-19(44)13-25(28)62-37(38)18-6-8-20(45)22(47)11-18/h4-13,15-16,26,29-31,33-36,39-48,50-52,54-57H,14H2,1-3H3/b9-5+/t15-,16-,26+,29-,30-,31-,33+,34+,35-,36+,39+,40+,41-,42+,43-/m0/s1
• InChI Key: XQSMSRSJNXQHLT-ABYIYZCWSA-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,5R,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]-4,5-dihydroxy-6-methyloxan-3-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	-	0.8803	88.03%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5729	57.29%
OATP2B1 inhibitior	-	0.7115	71.15%
OATP1B1 inhibitior	+	0.8717	87.17%
OATP1B3 inhibitior	+	0.9478	94.78%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7321	73.21%
P-glycoprotein inhibitior	+	0.6854	68.54%
P-glycoprotein substrate	+	0.7065	70.65%
CYP3A4 substrate	+	0.7080	70.80%
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	+	0.9054	90.54%
CYP inhibitory promiscuity	-	0.7459	74.59%
UGT catelyzed	+	0.7000	70.00%
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	-	0.6365	63.65%
Human Ether-a-go-go-Related Gene inhibition	+	0.6595	65.95%
Micronuclear	+	0.7092	70.92%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.9161	91.61%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.9886	98.86%
Acute Oral Toxicity (c)	III	0.5848	58.48%
Estrogen receptor binding	+	0.7887	78.87%
Androgen receptor binding	+	0.6191	61.91%
Thyroid receptor binding	+	0.5365	53.65%
Glucocorticoid receptor binding	+	0.6924	69.24%
Aromatase binding	+	0.5971	59.71%
PPAR gamma	+	0.7474	74.74%
Honey bee toxicity	-	0.6686	66.86%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
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	99.86%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	99.24%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.96%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	98.94%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.89%	96.00%
CHEMBL3194	P02766	Transthyretin	95.48%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.45%	96.09%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	94.36%	80.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.29%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.26%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.25%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.04%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	89.54%	95.64%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.78%	97.36%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.48%	95.50%
CHEMBL4208	P20618	Proteasome component C5	86.75%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.23%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.40%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.01%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.44%	85.14%
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: 11803929
• NPASS: NPC209528
• LOTUS: LTS0056511
• wikiData: Q105340012