5-Hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-3,7-bis[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one

Details

• Internal ID: 51e60b66-d402-4a94-854a-edb616cd6bb1
• 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)-3,7-bis[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C=C(C2=C1OC(=C(C2=O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC=C(C=C4)OC)O)OC5C(C(C(C(O5)CO)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=C(C2=C1OC(=C(C2=O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC=C(C=C4)OC)O)OC5C(C(C(C(O5)CO)O)O)O)C
• InChI: InChI=1S/C33H40O16/c1-13(2)4-9-16-18(45-32-27(42)25(40)22(37)19(11-34)46-32)10-17(36)21-24(39)31(49-33-28(43)26(41)23(38)20(12-35)47-33)29(48-30(16)21)14-5-7-15(44-3)8-6-14/h4-8,10,19-20,22-23,25-28,32-38,40-43H,9,11-12H2,1-3H3
• InChI Key: OKSDRSVOPASNHO-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₆
• Molecular Weight: 692.70 g/mol
• Exact Mass: 692.23163518 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): -0.96
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

• 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,7-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-4H-chromen-4-one
• 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-3,7-bis[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8164	81.64%
Caco-2	-	0.9252	92.52%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6461	64.61%
OATP2B1 inhibitior	-	0.5787	57.87%
OATP1B1 inhibitior	+	0.8966	89.66%
OATP1B3 inhibitior	+	0.9556	95.56%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8429	84.29%
P-glycoprotein inhibitior	+	0.6511	65.11%
P-glycoprotein substrate	-	0.6641	66.41%
CYP3A4 substrate	+	0.6407	64.07%
CYP2C9 substrate	-	0.8387	83.87%
CYP2D6 substrate	-	0.8462	84.62%
CYP3A4 inhibition	-	0.9605	96.05%
CYP2C9 inhibition	-	0.7520	75.20%
CYP2C19 inhibition	-	0.6564	65.64%
CYP2D6 inhibition	-	0.8523	85.23%
CYP1A2 inhibition	-	0.7720	77.20%
CYP2C8 inhibition	+	0.6403	64.03%
CYP inhibitory promiscuity	-	0.5971	59.71%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7249	72.49%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9108	91.08%
Skin irritation	-	0.8116	81.16%
Skin corrosion	-	0.9490	94.90%
Ames mutagenesis	+	0.5709	57.09%
Human Ether-a-go-go-Related Gene inhibition	+	0.7870	78.70%
Micronuclear	-	0.5167	51.67%
Hepatotoxicity	-	0.5540	55.40%
skin sensitisation	-	0.8660	86.60%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6346	63.46%
Acute Oral Toxicity (c)	III	0.6499	64.99%
Estrogen receptor binding	+	0.8060	80.60%
Androgen receptor binding	+	0.6815	68.15%
Thyroid receptor binding	+	0.5281	52.81%
Glucocorticoid receptor binding	+	0.5874	58.74%
Aromatase binding	+	0.5591	55.91%
PPAR gamma	+	0.6759	67.59%
Honey bee toxicity	-	0.7494	74.94%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9594	95.94%

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	99.79%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.11%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.10%	85.14%
CHEMBL2581	P07339	Cathepsin D	94.80%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.85%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	93.27%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.26%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.86%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.37%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.30%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.68%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.60%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.38%	86.92%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.75%	96.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.01%	95.50%
CHEMBL4208	P20618	Proteasome component C5	82.38%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.87%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.79%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.61%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.35%	92.62%

Plants that contains it

• Vancouveria hexandra

Cross-Links

• PubChem: 74978141
• LOTUS: LTS0210049
• wikiData: Q105193723