Patuletin 3-(2''-apiosyl-[2'''-feruloylgentiobioside])

Details

• Internal ID: d9de43ec-23d5-4877-9094-d42c0c936844
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6S)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4-oxochromen-3-yl]oxy-3,4-dihydroxyoxan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OC2C(C(C(OC2OCC3C(C(C(C(O3)OC4=C(OC5=C(C4=O)C(=C(C(=C5)O)OC)O)C6=CC(=C(C=C6)O)O)OC7C(C(CO7)(CO)O)O)O)O)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)OC4=C(OC5=C(C4=O)C(=C(C(=C5)O)OC)O)C6=CC(=C(C=C6)O)O)O[C@H]7[C@@H]([C@](CO7)(CO)O)O)O)O)CO)O)O)O
• InChI: InChI=1S/C43H48O25/c1-59-22-9-16(3-6-19(22)47)4-8-26(50)66-37-32(55)28(51)24(12-44)64-40(37)61-13-25-29(52)33(56)38(68-42-39(57)43(58,14-45)15-62-42)41(65-25)67-36-31(54)27-23(11-21(49)35(60-2)30(27)53)63-34(36)17-5-7-18(46)20(48)10-17/h3-11,24-25,28-29,32-33,37-42,44-49,51-53,55-58H,12-15H2,1-2H3/b8-4+/t24-,25-,28-,29-,32+,33+,37-,38-,39+,40-,41+,42+,43-/m1/s1
• InChI Key: VSMDAOFJZBLZOB-JFGFUAGISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₄₈O₂₅
• Molecular Weight: 964.80 g/mol
• Exact Mass: 964.24846701 g/mol
• Topological Polar Surface Area (TPSA): 389.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -2.26
• H-Bond Acceptor: 25
• H-Bond Donor: 13
• Rotatable Bonds: 15

Synonyms

• Patuletin 3-(2''-apiosyl-[2'''-feruloylgentiobioside])
• Patuletin 3-O-(2''-feruloylglucosyl)(1->6)-[apiosyl(1->2)]-glucoside
• 195206-61-2
• 3-[[O-D-Apio-beta-D-furanosyl-(1-->2)-O-[2-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]-beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one
• 3-[[O-D-Apio-beta-D-furanosyl-(1->2)-O-[2-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]-beta-D-glucopyranosyl-(1->6)]-beta-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one
• Patuletin 3-O-beta-D-(2''-feruloylglucopyranosyl)(1->6)-[beta-D-apiofuranosyl(1->2)]-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7004	70.04%
Caco-2	-	0.8735	87.35%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5797	57.97%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.8551	85.51%
OATP1B3 inhibitior	+	0.9685	96.85%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.5699	56.99%
P-glycoprotein inhibitior	+	0.7258	72.58%
P-glycoprotein substrate	+	0.6983	69.83%
CYP3A4 substrate	+	0.7305	73.05%
CYP2C9 substrate	-	0.8158	81.58%
CYP2D6 substrate	-	0.8657	86.57%
CYP3A4 inhibition	-	0.8009	80.09%
CYP2C9 inhibition	-	0.8644	86.44%
CYP2C19 inhibition	-	0.8596	85.96%
CYP2D6 inhibition	-	0.9210	92.10%
CYP1A2 inhibition	-	0.9189	91.89%
CYP2C8 inhibition	+	0.8640	86.40%
CYP inhibitory promiscuity	-	0.7816	78.16%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5380	53.80%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9034	90.34%
Skin irritation	-	0.8125	81.25%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.5728	57.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.7169	71.69%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8337	83.37%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.9820	98.20%
Acute Oral Toxicity (c)	III	0.5990	59.90%
Estrogen receptor binding	+	0.7834	78.34%
Androgen receptor binding	+	0.6556	65.56%
Thyroid receptor binding	+	0.5262	52.62%
Glucocorticoid receptor binding	+	0.6329	63.29%
Aromatase binding	+	0.6153	61.53%
PPAR gamma	+	0.7609	76.09%
Honey bee toxicity	-	0.6499	64.99%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.8920	89.20%

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	99.96%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	99.28%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.02%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.97%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.38%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.86%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.59%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.43%	97.09%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	91.99%	80.78%
CHEMBL226	P30542	Adenosine A1 receptor	90.65%	95.93%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	90.37%	94.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.21%	94.00%
CHEMBL2581	P07339	Cathepsin D	88.53%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.71%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.62%	86.92%
CHEMBL3194	P02766	Transthyretin	86.47%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.88%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	85.44%	91.49%
CHEMBL4208	P20618	Proteasome component C5	85.20%	90.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.75%	97.28%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.65%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.20%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.34%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.71%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.52%	92.94%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.95%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	81.68%	91.19%
CHEMBL4302	P08183	P-glycoprotein 1	81.62%	92.98%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.21%	91.03%
CHEMBL3401	O75469	Pregnane X receptor	80.49%	94.73%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.43%	96.90%

Plants that contains it

• Spinacia oleracea

Cross-Links

• PubChem: 101714006
• LOTUS: LTS0270823
• wikiData: Q105292343