[(2R,3R,4S,5R,6R)-3,5-dihydroxy-6-[2-(4-hydroxy-3-methoxy-phenyl)ethoxy]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]methyl (E)-3-(3-hydroxy-4-methoxy-phenyl)prop-2-enoate

Details

• Internal ID: e2e5326d-7121-4200-8d21-94c786ae3cd8
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4S,5R,6R)-3,5-dihydroxy-6-[2-(4-hydroxy-3-methoxyphenyl)ethoxy]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2O)OCCC3=CC(=C(C=C3)O)OC)COC(=O)C=CC4=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]2O)OCCC3=CC(=C(C=C3)O)OC)COC(=O)/C=C/C4=CC(=C(C=C4)OC)O)O)O)O)O
• InChI: InChI=1S/C31H40O15/c1-15-24(35)26(37)27(38)31(44-15)46-29-25(36)22(14-43-23(34)9-6-16-5-8-20(40-2)19(33)12-16)45-30(28(29)39)42-11-10-17-4-7-18(32)21(13-17)41-3/h4-9,12-13,15,22,24-33,35-39H,10-11,14H2,1-3H3/b9-6+/t15-,22+,24-,25+,26+,27+,28+,29-,30+,31-/m0/s1
• InChI Key: YRJXXSNZBARBSO-ZXLVUZSHSA-N
• Popularity: 3 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

• [(2R,3R,4S,5R,6R)-3,5-dihydroxy-6-[2-(4-hydroxy-3-methoxy-phenyl)ethoxy]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]methyl (E)-3-(3-hydroxy-4-methoxy-phenyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7485	74.85%
Caco-2	-	0.8970	89.70%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7443	74.43%
OATP2B1 inhibitior	-	0.8638	86.38%
OATP1B1 inhibitior	+	0.8732	87.32%
OATP1B3 inhibitior	+	0.9389	93.89%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7947	79.47%
P-glycoprotein inhibitior	-	0.4833	48.33%
P-glycoprotein substrate	+	0.5145	51.45%
CYP3A4 substrate	+	0.6715	67.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8608	86.08%
CYP3A4 inhibition	-	0.9188	91.88%
CYP2C9 inhibition	-	0.7805	78.05%
CYP2C19 inhibition	-	0.8494	84.94%
CYP2D6 inhibition	-	0.9000	90.00%
CYP1A2 inhibition	-	0.8746	87.46%
CYP2C8 inhibition	+	0.8536	85.36%
CYP inhibitory promiscuity	-	0.7303	73.03%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6501	65.01%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9279	92.79%
Skin irritation	-	0.8529	85.29%
Skin corrosion	-	0.9576	95.76%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6576	65.76%
Micronuclear	-	0.6467	64.67%
Hepatotoxicity	-	0.8591	85.91%
skin sensitisation	-	0.8765	87.65%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	-	0.9634	96.34%
Acute Oral Toxicity (c)	III	0.7764	77.64%
Estrogen receptor binding	+	0.8169	81.69%
Androgen receptor binding	-	0.5436	54.36%
Thyroid receptor binding	+	0.5692	56.92%
Glucocorticoid receptor binding	+	0.6854	68.54%
Aromatase binding	+	0.5201	52.01%
PPAR gamma	+	0.7089	70.89%
Honey bee toxicity	-	0.7339	73.39%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.8236	82.36%

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	99.18%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	99.09%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	98.35%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.76%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.88%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.76%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.57%	89.00%
CHEMBL3194	P02766	Transthyretin	93.61%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.84%	86.92%
CHEMBL2581	P07339	Cathepsin D	87.27%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	86.84%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.60%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.23%	90.71%
CHEMBL2179	P04062	Beta-glucocerebrosidase	83.73%	85.31%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.58%	94.45%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.98%	80.78%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.61%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.14%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.25%	95.89%
CHEMBL4208	P20618	Proteasome component C5	80.46%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.45%	97.36%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	80.38%	97.31%

Plants that contains it

• Plantago asiatica
• Prostanthera melissifolia
• Scutellaria albida subsp. albida

Cross-Links

• PubChem: 6476337
• NPASS: NPC75913
• LOTUS: LTS0209402
• wikiData: Q105352834