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

Details

• Internal ID: 038cf3e7-3c85-4dec-b1fc-262ee2c1e537
• 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-[[(6S)-6-(hydroxymethyl)-5,5-dimethyl-3-oxocyclohexen-1-yl]methoxy]oxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1(CC(=O)C=C(C1CO)COC2C(C(C(C(O2)COC(=O)C=CC3=CC(=C(C(=C3)OC)O)OC)O)O)O)C
• SMILES (Isomeric): CC1(CC(=O)C=C([C@H]1CO)CO[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
• InChI: InChI=1S/C27H36O12/c1-27(2)10-16(29)9-15(17(27)11-28)12-38-26-25(34)24(33)23(32)20(39-26)13-37-21(30)6-5-14-7-18(35-3)22(31)19(8-14)36-4/h5-9,17,20,23-26,28,31-34H,10-13H2,1-4H3/b6-5+/t17-,20-,23-,24+,25-,26-/m1/s1
• InChI Key: QDPPYFUKGGLDCP-FWMDYHNWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₆O₁₂
• Molecular Weight: 552.60 g/mol
• Exact Mass: 552.22067658 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 0.32
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7170	71.70%
Caco-2	-	0.8718	87.18%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8040	80.40%
OATP2B1 inhibitior	-	0.8638	86.38%
OATP1B1 inhibitior	+	0.8230	82.30%
OATP1B3 inhibitior	+	0.8746	87.46%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7175	71.75%
P-glycoprotein inhibitior	+	0.6284	62.84%
P-glycoprotein substrate	-	0.5623	56.23%
CYP3A4 substrate	+	0.6757	67.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8802	88.02%
CYP3A4 inhibition	-	0.7675	76.75%
CYP2C9 inhibition	-	0.6854	68.54%
CYP2C19 inhibition	-	0.6283	62.83%
CYP2D6 inhibition	-	0.9028	90.28%
CYP1A2 inhibition	-	0.5984	59.84%
CYP2C8 inhibition	+	0.6827	68.27%
CYP inhibitory promiscuity	-	0.8669	86.69%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7059	70.59%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9355	93.55%
Skin irritation	-	0.8122	81.22%
Skin corrosion	-	0.9543	95.43%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4841	48.41%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.6572	65.72%
skin sensitisation	-	0.8209	82.09%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.7263	72.63%
Acute Oral Toxicity (c)	III	0.5846	58.46%
Estrogen receptor binding	+	0.7982	79.82%
Androgen receptor binding	+	0.6318	63.18%
Thyroid receptor binding	+	0.5295	52.95%
Glucocorticoid receptor binding	+	0.6882	68.82%
Aromatase binding	+	0.6355	63.55%
PPAR gamma	+	0.6682	66.82%
Honey bee toxicity	-	0.7901	79.01%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9912	99.12%

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	99.75%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.76%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.31%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.45%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.36%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.02%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.75%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.83%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.34%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.60%	92.94%
CHEMBL5255	O00206	Toll-like receptor 4	88.52%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.12%	99.17%
CHEMBL2581	P07339	Cathepsin D	87.52%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.16%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.17%	96.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.34%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.44%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.36%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	81.32%	95.93%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.20%	94.33%
CHEMBL3194	P02766	Transthyretin	80.37%	90.71%

Plants that contains it

• Gardenia jasminoides

Cross-Links

• PubChem: 163190562
• LOTUS: LTS0198696
• wikiData: Q105218915