[(2R,3R,4R,5R,6R)-5-hydroxy-6-[2-(3-hydroxy-4-methoxyphenyl)ethoxy]-2-(hydroxymethyl)-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: 71de9648-7c27-4f23-9c71-d338f1e58c4c
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4R,5R,6R)-5-hydroxy-6-[2-(3-hydroxy-4-methoxyphenyl)ethoxy]-2-(hydroxymethyl)-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)OC)CO)OCCC4=CC(=C(C=C4)OC)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H]([C@@H]([C@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)OC)CO)OCCC4=CC(=C(C=C4)OC)O)O)O)O)O
• InChI: InChI=1S/C31H40O15/c1-15-24(36)25(37)26(38)31(43-15)46-29-27(39)30(42-11-10-17-5-8-20(40-2)19(34)12-17)44-22(14-32)28(29)45-23(35)9-6-16-4-7-18(33)21(13-16)41-3/h4-9,12-13,15,22,24-34,36-39H,10-11,14H2,1-3H3/b9-6+/t15-,22-,24-,25+,26+,27-,28-,29-,30-,31-/m1/s1
• InChI Key: WLWAYPFRKDSFCL-PMQRAQSFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₀O₁₅
• Molecular Weight: 652.60 g/mol
• Exact Mass: 652.23672056 g/mol
• Topological Polar Surface Area (TPSA): 223.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.41
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7814	78.14%
Caco-2	-	0.9017	90.17%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7303	73.03%
OATP2B1 inhibitior	-	0.8621	86.21%
OATP1B1 inhibitior	+	0.8787	87.87%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7854	78.54%
P-glycoprotein inhibitior	-	0.4703	47.03%
P-glycoprotein substrate	+	0.5153	51.53%
CYP3A4 substrate	+	0.6685	66.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8621	86.21%
CYP3A4 inhibition	-	0.8790	87.90%
CYP2C9 inhibition	-	0.8119	81.19%
CYP2C19 inhibition	-	0.8663	86.63%
CYP2D6 inhibition	-	0.9035	90.35%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.8092	80.92%
CYP inhibitory promiscuity	-	0.6839	68.39%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6779	67.79%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9269	92.69%
Skin irritation	-	0.8502	85.02%
Skin corrosion	-	0.9613	96.13%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6947	69.47%
Micronuclear	-	0.6567	65.67%
Hepatotoxicity	-	0.9000	90.00%
skin sensitisation	-	0.8582	85.82%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.9561	95.61%
Acute Oral Toxicity (c)	III	0.7777	77.77%
Estrogen receptor binding	+	0.8209	82.09%
Androgen receptor binding	-	0.6288	62.88%
Thyroid receptor binding	+	0.5711	57.11%
Glucocorticoid receptor binding	+	0.6961	69.61%
Aromatase binding	-	0.4904	49.04%
PPAR gamma	+	0.6914	69.14%
Honey bee toxicity	-	0.6809	68.09%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.6878	68.78%

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	99.41%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.21%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.72%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.74%	96.00%
CHEMBL3194	P02766	Transthyretin	95.34%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.70%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.59%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.55%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	88.35%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	87.25%	91.49%
CHEMBL2581	P07339	Cathepsin D	85.73%	98.95%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.89%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.25%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.28%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.90%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.78%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.29%	95.89%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.21%	80.78%

Plants that contains it

• Clerodendrum trichotomum
• Paulownia tomentosa
• Pedicularis plicata
• Plantago lanceolata
• Rehmannia glutinosa

Cross-Links

• PubChem: 44429856
• NPASS: NPC165932
• LOTUS: LTS0096857
• wikiData: Q105308294