[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(1R)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]methoxy]oxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

Details

• Internal ID: 3165c872-61e3-40af-b725-4bf48fe05601
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(1R)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]methoxy]oxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1=CC(=O)CC(C1COC2C(C(C(C(O2)COC(=O)C=CC3=CC(=C(C(=C3)OC)O)OC)O)O)O)(C)C
• SMILES (Isomeric): CC1=CC(=O)CC([C@H]1CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)/C=C/C3=CC(=C(C(=C3)OC)O)OC)O)O)O)(C)C
• InChI: InChI=1S/C27H36O11/c1-14-8-16(28)11-27(2,3)17(14)12-37-26-25(33)24(32)23(31)20(38-26)13-36-21(29)7-6-15-9-18(34-4)22(30)19(10-15)35-5/h6-10,17,20,23-26,30-33H,11-13H2,1-5H3/b7-6+/t17-,20+,23+,24-,25+,26+/m0/s1
• InChI Key: SGHMUAWQXUYUAJ-JALQXBGLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₆O₁₁
• Molecular Weight: 536.60 g/mol
• Exact Mass: 536.22576196 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.35
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7385	73.85%
Caco-2	-	0.8351	83.51%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7803	78.03%
OATP2B1 inhibitior	-	0.8613	86.13%
OATP1B1 inhibitior	+	0.8250	82.50%
OATP1B3 inhibitior	+	0.8982	89.82%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7339	73.39%
P-glycoprotein inhibitior	+	0.6701	67.01%
P-glycoprotein substrate	-	0.5911	59.11%
CYP3A4 substrate	+	0.6877	68.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8801	88.01%
CYP3A4 inhibition	-	0.8323	83.23%
CYP2C9 inhibition	-	0.5889	58.89%
CYP2C19 inhibition	-	0.5732	57.32%
CYP2D6 inhibition	-	0.8758	87.58%
CYP1A2 inhibition	-	0.5229	52.29%
CYP2C8 inhibition	+	0.6458	64.58%
CYP inhibitory promiscuity	-	0.7957	79.57%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6620	66.20%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9294	92.94%
Skin irritation	-	0.8115	81.15%
Skin corrosion	-	0.9485	94.85%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5639	56.39%
Micronuclear	-	0.6526	65.26%
Hepatotoxicity	-	0.7323	73.23%
skin sensitisation	-	0.7804	78.04%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8888	88.88%
Acute Oral Toxicity (c)	III	0.6292	62.92%
Estrogen receptor binding	+	0.7403	74.03%
Androgen receptor binding	+	0.5678	56.78%
Thyroid receptor binding	+	0.5583	55.83%
Glucocorticoid receptor binding	+	0.7138	71.38%
Aromatase binding	+	0.6693	66.93%
PPAR gamma	+	0.6774	67.74%
Honey bee toxicity	-	0.7968	79.68%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9916	99.16%

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	99.66%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.95%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.74%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.38%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.37%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.57%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.39%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.94%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.81%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	88.68%	92.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.91%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.59%	96.95%
CHEMBL2581	P07339	Cathepsin D	85.09%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.87%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	82.86%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.67%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.58%	96.21%
CHEMBL1871	P10275	Androgen Receptor	82.22%	96.43%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.76%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.72%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.40%	99.17%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.66%	96.61%
CHEMBL4208	P20618	Proteasome component C5	80.46%	90.00%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	80.34%	98.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.24%	99.23%

Plants that contains it

• Gardenia jasminoides

Cross-Links

• PubChem: 102596098
• LOTUS: LTS0022160
• wikiData: Q105252321