[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-6-methoxy-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 2-methylpropanoate

Details

• Internal ID: 9cfc8b27-a362-4c67-ae0a-204e1376f073
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-6-methoxy-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 2-methylpropanoate
• SMILES (Canonical): CC(C)C(=O)OCC1C(C(C(C(O1)OC2=C(C(=C3C(=C2)OC(=C(C3=O)O)C4=CC(=C(C=C4)O)O)O)OC)O)O)O
• SMILES (Isomeric): CC(C)C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=C(C(=C3C(=C2)OC(=C(C3=O)O)C4=CC(=C(C=C4)O)O)O)OC)O)O)O
• InChI: InChI=1S/C26H28O14/c1-9(2)25(35)37-8-15-17(29)20(32)22(34)26(40-15)39-14-7-13-16(19(31)24(14)36-3)18(30)21(33)23(38-13)10-4-5-11(27)12(28)6-10/h4-7,9,15,17,20,22,26-29,31-34H,8H2,1-3H3/t15-,17-,20+,22-,26-/m1/s1
• InChI Key: AIDVHFDSVRUDAJ-BUEDXGQVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₄
• Molecular Weight: 564.50 g/mol
• Exact Mass: 564.14790556 g/mol
• Topological Polar Surface Area (TPSA): 222.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 0.68
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• Patuletin 7-(6-isobutyrylglucoside)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5000	50.00%
Caco-2	-	0.8845	88.45%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7061	70.61%
OATP2B1 inhibitior	-	0.5665	56.65%
OATP1B1 inhibitior	+	0.8822	88.22%
OATP1B3 inhibitior	+	0.9172	91.72%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7838	78.38%
P-glycoprotein inhibitior	-	0.4376	43.76%
P-glycoprotein substrate	-	0.5147	51.47%
CYP3A4 substrate	+	0.6467	64.67%
CYP2C9 substrate	-	0.6356	63.56%
CYP2D6 substrate	-	0.8712	87.12%
CYP3A4 inhibition	-	0.9026	90.26%
CYP2C9 inhibition	-	0.7607	76.07%
CYP2C19 inhibition	-	0.8916	89.16%
CYP2D6 inhibition	-	0.9315	93.15%
CYP1A2 inhibition	-	0.8546	85.46%
CYP2C8 inhibition	+	0.8110	81.10%
CYP inhibitory promiscuity	-	0.8007	80.07%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6700	67.00%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9053	90.53%
Skin irritation	-	0.8560	85.60%
Skin corrosion	-	0.9573	95.73%
Ames mutagenesis	+	0.5036	50.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4267	42.67%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.9257	92.57%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.9779	97.79%
Acute Oral Toxicity (c)	III	0.6705	67.05%
Estrogen receptor binding	+	0.8501	85.01%
Androgen receptor binding	+	0.6323	63.23%
Thyroid receptor binding	+	0.6014	60.14%
Glucocorticoid receptor binding	+	0.7574	75.74%
Aromatase binding	+	0.5434	54.34%
PPAR gamma	+	0.6937	69.37%
Honey bee toxicity	-	0.7589	75.89%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7149	71.49%
Fish aquatic toxicity	+	0.9289	92.89%

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	99.74%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.96%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.63%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	96.13%	99.15%
CHEMBL2581	P07339	Cathepsin D	96.03%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	95.28%	95.64%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.34%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.14%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.88%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.83%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.89%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.39%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	89.00%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.37%	92.62%
CHEMBL213	P08588	Beta-1 adrenergic receptor	83.07%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	83.00%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.92%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.92%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.73%	94.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.17%	99.23%

Plants that contains it

• Buphthalmum salicifolium
• Pentanema britannicum

Cross-Links

• PubChem: 10076594
• NPASS: NPC233994
• LOTUS: LTS0115300
• wikiData: Q104912675