[(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-3-yl] (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

Details

• Internal ID: 94503b37-2a5d-4383-a366-8d995ec167e3
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-3-yl] (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C=CC(=O)OC2C(C(OC2(CO)OC3C(C(C(C(O3)CO)O)O)O)CO)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)/C=C/C(=O)O[C@H]2[C@@H]([C@H](O[C@@]2(CO)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO)O
• InChI: InChI=1S/C23H32O15/c1-33-11-5-10(6-12(34-2)16(11)28)3-4-15(27)36-21-18(30)14(8-25)37-23(21,9-26)38-22-20(32)19(31)17(29)13(7-24)35-22/h3-6,13-14,17-22,24-26,28-32H,7-9H2,1-2H3/b4-3+/t13-,14-,17-,18-,19+,20-,21+,22+,23+/m1/s1
• InChI Key: WTCVROXOIQEIRC-VBFFRYFESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₂O₁₅
• Molecular Weight: 548.50 g/mol
• Exact Mass: 548.17412031 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -3.41
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

• AKOS037514964

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7467	74.67%
Caco-2	-	0.8899	88.99%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7553	75.53%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8400	84.00%
OATP1B3 inhibitior	+	0.9612	96.12%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7358	73.58%
P-glycoprotein inhibitior	-	0.5914	59.14%
P-glycoprotein substrate	-	0.6950	69.50%
CYP3A4 substrate	+	0.6160	61.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8593	85.93%
CYP3A4 inhibition	-	0.7762	77.62%
CYP2C9 inhibition	-	0.8583	85.83%
CYP2C19 inhibition	-	0.7722	77.22%
CYP2D6 inhibition	-	0.9013	90.13%
CYP1A2 inhibition	-	0.8923	89.23%
CYP2C8 inhibition	+	0.6448	64.48%
CYP inhibitory promiscuity	-	0.5878	58.78%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6660	66.60%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9302	93.02%
Skin irritation	-	0.8418	84.18%
Skin corrosion	-	0.9570	95.70%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4418	44.18%
Micronuclear	-	0.6026	60.26%
Hepatotoxicity	-	0.8444	84.44%
skin sensitisation	-	0.7967	79.67%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8771	87.71%
Acute Oral Toxicity (c)	III	0.6841	68.41%
Estrogen receptor binding	+	0.8217	82.17%
Androgen receptor binding	+	0.5377	53.77%
Thyroid receptor binding	+	0.5362	53.62%
Glucocorticoid receptor binding	-	0.4651	46.51%
Aromatase binding	+	0.6546	65.46%
PPAR gamma	+	0.6624	66.24%
Honey bee toxicity	-	0.7191	71.91%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.8298	82.98%

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	99.38%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.43%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.13%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.01%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.36%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.90%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	91.90%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.21%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.75%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.64%	92.94%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.88%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.82%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.74%	97.36%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.60%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.67%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.23%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	80.20%	92.50%
CHEMBL3194	P02766	Transthyretin	80.05%	90.71%

Plants that contains it

• Polygala sibirica
• Polygala tenuifolia

Cross-Links

• PubChem: 102004866
• NPASS: NPC61355