3,5-dihydroxy-6-(3-hydroxy-3-methylbutyl)-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one

Details

• Internal ID: c4072e8b-66b0-4de6-8480-04d23470bf6d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3,5-dihydroxy-6-(3-hydroxy-3-methylbutyl)-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(C)(CCC1=C(C=C2C(=C1O)C(=O)C(C(O2)C3=CC=C(C=C3)O)O)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): CC(C)(CCC1=C(C=C2C(=C1O)C(=O)C(C(O2)C3=CC=C(C=C3)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C26H32O12/c1-26(2,35)8-7-13-14(37-25-23(34)21(32)19(30)16(10-27)38-25)9-15-17(18(13)29)20(31)22(33)24(36-15)11-3-5-12(28)6-4-11/h3-6,9,16,19,21-25,27-30,32-35H,7-8,10H2,1-2H3/t16-,19-,21+,22?,23-,24?,25-/m1/s1
• InChI Key: YXACCHLOUSCDDR-OAOFYEKTSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₂
• Molecular Weight: 536.50 g/mol
• Exact Mass: 536.18937645 g/mol
• Topological Polar Surface Area (TPSA): 207.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -0.34
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8088	80.88%
Caco-2	-	0.8953	89.53%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.7679	76.79%
OATP2B1 inhibitior	-	0.8491	84.91%
OATP1B1 inhibitior	+	0.7865	78.65%
OATP1B3 inhibitior	+	0.9093	90.93%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8537	85.37%
BSEP inhibitior	+	0.8646	86.46%
P-glycoprotein inhibitior	-	0.5304	53.04%
P-glycoprotein substrate	-	0.6976	69.76%
CYP3A4 substrate	+	0.6525	65.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8566	85.66%
CYP3A4 inhibition	-	0.8261	82.61%
CYP2C9 inhibition	-	0.8690	86.90%
CYP2C19 inhibition	-	0.9155	91.55%
CYP2D6 inhibition	-	0.9175	91.75%
CYP1A2 inhibition	-	0.7363	73.63%
CYP2C8 inhibition	+	0.6928	69.28%
CYP inhibitory promiscuity	-	0.9143	91.43%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6766	67.66%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.8716	87.16%
Skin irritation	-	0.7808	78.08%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.5654	56.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4388	43.88%
Micronuclear	-	0.6926	69.26%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.9121	91.21%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.6552	65.52%
Acute Oral Toxicity (c)	III	0.6281	62.81%
Estrogen receptor binding	+	0.7667	76.67%
Androgen receptor binding	+	0.6302	63.02%
Thyroid receptor binding	+	0.5535	55.35%
Glucocorticoid receptor binding	+	0.6326	63.26%
Aromatase binding	+	0.6687	66.87%
PPAR gamma	+	0.7416	74.16%
Honey bee toxicity	-	0.7655	76.55%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5049	50.49%
Fish aquatic toxicity	+	0.9368	93.68%

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	99.16%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.31%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.82%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	94.70%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.98%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.84%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.12%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.36%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.83%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.76%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.35%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.49%	99.23%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.36%	90.93%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.26%	95.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.92%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.09%	96.95%

Plants that contains it

• Phellodendron amurense

Cross-Links

• PubChem: 5320517
• NPASS: NPC174554