3,4,6,7-Tetrahydroxy-2-(hydroxymethyl)-8-[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]-9-oxo-3,4,4a,6,9,9b-hexahydro-2H-pyrano[3,2-b][1]benzo[b]furan-6-yl beta-D-glucopyranoside

Details

• Internal ID: ef50bfe2-ae22-4f65-bd91-a76983ea005a
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives
• IUPAC Name: 3,4,6,9-tetrahydroxy-2-(hydroxymethyl)-8-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,4a,9b-tetrahydro-2H-pyrano[3,2-b][1]benzofuran-7-one
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)C2=C(C3=C(C(C2=O)(O)OC4C(C(C(C(O4)CO)O)O)O)OC5C3OC(C(C5O)O)CO)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C(=O)C2=C(C3=C(C(C2=O)(O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC5C3OC(C(C5O)O)CO)O)O
• InChI: InChI=1S/C27H30O16/c28-7-12-17(33)20(36)23-22(40-12)15-18(34)14(11(31)6-3-9-1-4-10(30)5-2-9)24(38)27(39,25(15)42-23)43-26-21(37)19(35)16(32)13(8-29)41-26/h1-6,12-13,16-17,19-23,26,28-30,32-37,39H,7-8H2/b6-3+/t12?,13-,16-,17?,19+,20?,21-,22?,23?,26+,27?/m1/s1
• InChI Key: AQMZAOSKHKZGNI-BRESOZKGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₆
• Molecular Weight: 610.50 g/mol
• Exact Mass: 610.15338487 g/mol
• Topological Polar Surface Area (TPSA): 273.00 Ų
• XlogP: -3.10
• Atomic LogP (AlogP): -3.99
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 7

Synonyms

• 3,4,6,7-Tetrahydroxy-2-(hydroxymethyl)-8-[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]-9-oxo-3,4,4a,6,9,9b-hexahydro-2H-pyrano[3,2-b][1]benzo[b]furan-6-yl beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5791	57.91%
Caco-2	-	0.9191	91.91%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7355	73.55%
OATP2B1 inhibitior	-	0.7024	70.24%
OATP1B1 inhibitior	+	0.8354	83.54%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6476	64.76%
P-glycoprotein inhibitior	-	0.5382	53.82%
P-glycoprotein substrate	-	0.7829	78.29%
CYP3A4 substrate	+	0.6338	63.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8622	86.22%
CYP3A4 inhibition	-	0.8799	87.99%
CYP2C9 inhibition	-	0.7891	78.91%
CYP2C19 inhibition	-	0.7179	71.79%
CYP2D6 inhibition	-	0.8659	86.59%
CYP1A2 inhibition	-	0.8461	84.61%
CYP2C8 inhibition	+	0.6076	60.76%
CYP inhibitory promiscuity	-	0.6638	66.38%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5384	53.84%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.9013	90.13%
Skin irritation	-	0.7698	76.98%
Skin corrosion	-	0.9417	94.17%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6572	65.72%
Micronuclear	+	0.5233	52.33%
Hepatotoxicity	-	0.7082	70.82%
skin sensitisation	-	0.8170	81.70%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.5796	57.96%
Acute Oral Toxicity (c)	III	0.4565	45.65%
Estrogen receptor binding	+	0.7608	76.08%
Androgen receptor binding	+	0.6933	69.33%
Thyroid receptor binding	-	0.5545	55.45%
Glucocorticoid receptor binding	-	0.5316	53.16%
Aromatase binding	+	0.5961	59.61%
PPAR gamma	+	0.6769	67.69%
Honey bee toxicity	-	0.7434	74.34%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9029	90.29%

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	99.22%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.76%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.38%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.36%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.29%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.22%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.22%	89.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.99%	91.71%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.94%	89.67%
CHEMBL3401	O75469	Pregnane X receptor	84.48%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.60%	99.17%
CHEMBL2581	P07339	Cathepsin D	82.95%	98.95%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.63%	94.62%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.26%	94.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.76%	96.09%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.07%	85.00%

Plants that contains it

• Carthamus tinctorius

Cross-Links

• PubChem: 71463725
• NPASS: NPC283584