[(2R,3S,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 0c2733e4-67b2-4f01-bf5f-b049540d1742
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid 3-O-p-coumaroyl glycosides
• IUPAC Name: [(2R,3S,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C(=O)OC[C@@H]2[C@H](C(C([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O
• InChI: InChI=1S/C30H26O14/c31-15-5-1-13(2-6-15)3-8-22(36)41-12-21-24(37)26(39)27(40)30(43-21)44-29-25(38)23-19(35)10-16(32)11-20(23)42-28(29)14-4-7-17(33)18(34)9-14/h1-11,21,24,26-27,30-35,37,39-40H,12H2/b8-3+/t21-,24-,26?,27?,30+/m1/s1
• InChI Key: NBAZENYUDPJQIH-JUTLVVRMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₆O₁₄
• Molecular Weight: 610.50 g/mol
• Exact Mass: 610.13225550 g/mol
• Topological Polar Surface Area (TPSA): 233.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.43
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• LMPK12112144

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4689	46.89%
Caco-2	-	0.9100	91.00%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5846	58.46%
OATP2B1 inhibitior	-	0.5528	55.28%
OATP1B1 inhibitior	+	0.8833	88.33%
OATP1B3 inhibitior	+	0.9635	96.35%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.4767	47.67%
P-glycoprotein inhibitior	+	0.6355	63.55%
P-glycoprotein substrate	-	0.6105	61.05%
CYP3A4 substrate	+	0.6737	67.37%
CYP2C9 substrate	-	0.8118	81.18%
CYP2D6 substrate	-	0.8706	87.06%
CYP3A4 inhibition	-	0.8901	89.01%
CYP2C9 inhibition	-	0.8448	84.48%
CYP2C19 inhibition	-	0.8659	86.59%
CYP2D6 inhibition	-	0.9392	93.92%
CYP1A2 inhibition	-	0.9312	93.12%
CYP2C8 inhibition	+	0.9300	93.00%
CYP inhibitory promiscuity	-	0.7755	77.55%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6770	67.70%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.8918	89.18%
Skin irritation	-	0.8069	80.69%
Skin corrosion	-	0.9555	95.55%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4654	46.54%
Micronuclear	+	0.7292	72.92%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8777	87.77%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9293	92.93%
Acute Oral Toxicity (c)	III	0.4048	40.48%
Estrogen receptor binding	+	0.7475	74.75%
Androgen receptor binding	+	0.8258	82.58%
Thyroid receptor binding	+	0.5137	51.37%
Glucocorticoid receptor binding	+	0.6421	64.21%
Aromatase binding	+	0.5360	53.60%
PPAR gamma	+	0.6724	67.24%
Honey bee toxicity	-	0.7235	72.35%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9677	96.77%

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	99.64%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.54%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	97.89%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.07%	86.33%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	96.79%	95.64%
CHEMBL3194	P02766	Transthyretin	96.48%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.33%	99.17%
CHEMBL2581	P07339	Cathepsin D	91.89%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	89.43%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.46%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.21%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.04%	94.45%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	87.91%	80.78%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.81%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.68%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.64%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.37%	95.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.75%	90.71%
CHEMBL1900	P15121	Aldose reductase	81.68%	92.38%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.36%	95.50%

Plants that contains it

• Crocus sativus
• Helianthus annuus

Cross-Links

• PubChem: 44259193
• NPASS: NPC200324