methyl (1R,3S,7R,7aR)-7-hydroxy-3-methoxy-7-methyl-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-3,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 1fe83a4a-d84c-4c25-9803-2ef7c2a12acf
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: methyl (1R,3S,7R,7aR)-7-hydroxy-3-methoxy-7-methyl-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-3,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1(CCC2=C(C(OC(C21)OC3C(C(C(C(O3)COC(=O)C=CC4=CC=C(C=C4)O)O)O)O)OC)C(=O)OC)O
• SMILES (Isomeric): C[C@]1(CCC2=C([C@H](O[C@@H]([C@H]21)O[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)COC(=O)/C=C/C4=CC=C(C=C4)O)O)O)O)OC)C(=O)OC)O
• InChI: InChI=1S/C27H34O13/c1-27(34)11-10-15-18(23(33)35-2)24(36-3)39-25(19(15)27)40-26-22(32)21(31)20(30)16(38-26)12-37-17(29)9-6-13-4-7-14(28)8-5-13/h4-9,16,19-22,24-26,28,30-32,34H,10-12H2,1-3H3/b9-6+/t16-,19-,20-,21+,22-,24-,25+,26+,27+/m0/s1
• InChI Key: WDVZASUHGJGVQO-XVHOMBRNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₁₃
• Molecular Weight: 566.50 g/mol
• Exact Mass: 566.19994113 g/mol
• Topological Polar Surface Area (TPSA): 191.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.27
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8891	88.91%
Caco-2	-	0.8665	86.65%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7088	70.88%
OATP2B1 inhibitior	-	0.8617	86.17%
OATP1B1 inhibitior	+	0.8361	83.61%
OATP1B3 inhibitior	+	0.8890	88.90%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8271	82.71%
BSEP inhibitior	-	0.6594	65.94%
P-glycoprotein inhibitior	-	0.4732	47.32%
P-glycoprotein substrate	-	0.5270	52.70%
CYP3A4 substrate	+	0.7202	72.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8863	88.63%
CYP3A4 inhibition	-	0.8523	85.23%
CYP2C9 inhibition	-	0.8186	81.86%
CYP2C19 inhibition	-	0.8804	88.04%
CYP2D6 inhibition	-	0.9054	90.54%
CYP1A2 inhibition	-	0.8023	80.23%
CYP2C8 inhibition	+	0.7428	74.28%
CYP inhibitory promiscuity	-	0.8695	86.95%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5508	55.08%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9299	92.99%
Skin irritation	-	0.6063	60.63%
Skin corrosion	-	0.9285	92.85%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4377	43.77%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.6800	68.00%
skin sensitisation	-	0.8801	88.01%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.8949	89.49%
Acute Oral Toxicity (c)	I	0.4750	47.50%
Estrogen receptor binding	+	0.7827	78.27%
Androgen receptor binding	+	0.6826	68.26%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7103	71.03%
Aromatase binding	+	0.5330	53.30%
PPAR gamma	+	0.6847	68.47%
Honey bee toxicity	-	0.7405	74.05%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9483	94.83%

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	99.24%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.33%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.78%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	92.58%	90.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.53%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.84%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.49%	89.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	88.23%	93.10%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.15%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	85.51%	94.73%
CHEMBL2581	P07339	Cathepsin D	84.96%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.15%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.06%	94.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.86%	94.45%
CHEMBL5255	O00206	Toll-like receptor 4	83.76%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.56%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.05%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.97%	95.89%
CHEMBL5028	O14672	ADAM10	82.44%	97.50%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.43%	95.64%
CHEMBL1937	Q92769	Histone deacetylase 2	82.42%	94.75%
CHEMBL5957	P21589	5'-nucleotidase	82.06%	97.78%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.01%	91.07%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.92%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	80.39%	95.93%
CHEMBL4208	P20618	Proteasome component C5	80.08%	90.00%

Plants that contains it

• Phlomis brunneogaleata

Cross-Links

• PubChem: 163194610
• LOTUS: LTS0112356
• wikiData: Q105302714