3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one

Details

• Internal ID: 2050486a-f866-4718-816c-15adab7aae05
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)OC4C(C(C(C(O4)CO)O)O)O)O)C5=CC=C(C=C5)OC)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H](C(O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)OC4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C5=CC=C(C=C5)OC)O)O)O
• InChI: InChI=1S/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32?,33?/m0/s1
• InChI Key: TZJALUIVHRYQQB-XGYHSCOOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₅
• Molecular Weight: 676.70 g/mol
• Exact Mass: 676.23672056 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 0.07
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

• SCHEMBL13038047
• TZJALUIVHRYQQB-XGYHSCOOSA-N
• HMS3884P11
• s2312
• AKOS015894974
• AC-6049
• CCG-270362
• AS-11644
• 3-[(6-Deoxy-.alpha.-L-mannopyranosyl)oxy]-7-(.beta.-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8585	85.85%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6495	64.95%
OATP2B1 inhibitior	-	0.5758	57.58%
OATP1B1 inhibitior	+	0.8807	88.07%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8472	84.72%
P-glycoprotein inhibitior	+	0.6382	63.82%
P-glycoprotein substrate	-	0.5343	53.43%
CYP3A4 substrate	+	0.6488	64.88%
CYP2C9 substrate	-	0.8387	83.87%
CYP2D6 substrate	-	0.8462	84.62%
CYP3A4 inhibition	-	0.9306	93.06%
CYP2C9 inhibition	-	0.7318	73.18%
CYP2C19 inhibition	-	0.6575	65.75%
CYP2D6 inhibition	-	0.8183	81.83%
CYP1A2 inhibition	-	0.7072	70.72%
CYP2C8 inhibition	+	0.6611	66.11%
CYP inhibitory promiscuity	-	0.5487	54.87%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7378	73.78%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9079	90.79%
Skin irritation	-	0.8008	80.08%
Skin corrosion	-	0.9495	94.95%
Ames mutagenesis	+	0.5172	51.72%
Human Ether-a-go-go-Related Gene inhibition	+	0.7132	71.32%
Micronuclear	+	0.5033	50.33%
Hepatotoxicity	-	0.5448	54.48%
skin sensitisation	-	0.8766	87.66%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.7847	78.47%
Acute Oral Toxicity (c)	III	0.6326	63.26%
Estrogen receptor binding	+	0.7985	79.85%
Androgen receptor binding	+	0.6487	64.87%
Thyroid receptor binding	+	0.5382	53.82%
Glucocorticoid receptor binding	+	0.6406	64.06%
Aromatase binding	+	0.5685	56.85%
PPAR gamma	+	0.6904	69.04%
Honey bee toxicity	-	0.7280	72.80%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9668	96.68%

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	99.85%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.60%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.52%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.66%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.92%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.88%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	93.43%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.16%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.11%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.46%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.81%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	90.32%	91.49%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.23%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.47%	94.45%
CHEMBL4208	P20618	Proteasome component C5	82.49%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.33%	97.36%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.00%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.46%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.15%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.05%	96.95%

Plants that contains it

• Crataegus pinnatifida
• Epimedium brevicornu
• Phlomoides rotata

Cross-Links

• PubChem: 45358132
• NPASS: NPC20763