[(2R,3R,4S,5S,6R)-2-[(1R,2E,3S,4R,5S)-2-(cyanomethylidene)-3-hydroxy-4,5-dimethoxycyclohexyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: 51c0c44c-41ec-4f45-a49c-8d69d830e143
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4S,5S,6R)-2-[(1R,2E,3S,4R,5S)-2-(cyanomethylidene)-3-hydroxy-4,5-dimethoxycyclohexyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1CC(C(=CC#N)C(C1OC)O)OC2C(C(C(C(O2)CO)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)OC
• SMILES (Isomeric): CO[C@H]1C[C@H](/C(=C/C#N)/[C@@H]([C@H]1OC)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)OC
• InChI: InChI=1S/C26H33NO12/c1-34-17-10-13(4-6-15(17)29)5-7-20(30)39-25-23(33)22(32)19(12-28)38-26(25)37-16-11-18(35-2)24(36-3)21(31)14(16)8-9-27/h4-8,10,16,18-19,21-26,28-29,31-33H,11-12H2,1-3H3/b7-5+,14-8-/t16-,18+,19-,21+,22-,23+,24+,25-,26-/m1/s1
• InChI Key: GWXJMPVVJCHQIB-WSVSSVRQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₃NO₁₂
• Molecular Weight: 551.50 g/mol
• Exact Mass: 551.20027549 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -0.61
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6123	61.23%
Caco-2	-	0.8776	87.76%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5702	57.02%
OATP2B1 inhibitior	-	0.8636	86.36%
OATP1B1 inhibitior	+	0.8458	84.58%
OATP1B3 inhibitior	+	0.9425	94.25%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7094	70.94%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.5317	53.17%
CYP3A4 substrate	+	0.6755	67.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8515	85.15%
CYP3A4 inhibition	-	0.7241	72.41%
CYP2C9 inhibition	-	0.7126	71.26%
CYP2C19 inhibition	-	0.7082	70.82%
CYP2D6 inhibition	-	0.8198	81.98%
CYP1A2 inhibition	-	0.6111	61.11%
CYP2C8 inhibition	+	0.6766	67.66%
CYP inhibitory promiscuity	+	0.5075	50.75%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7680	76.80%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9335	93.35%
Skin irritation	-	0.8009	80.09%
Skin corrosion	-	0.9591	95.91%
Ames mutagenesis	-	0.5964	59.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7368	73.68%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8236	82.36%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9337	93.37%
Acute Oral Toxicity (c)	III	0.6231	62.31%
Estrogen receptor binding	+	0.7644	76.44%
Androgen receptor binding	-	0.5124	51.24%
Thyroid receptor binding	+	0.5651	56.51%
Glucocorticoid receptor binding	+	0.6180	61.80%
Aromatase binding	+	0.5378	53.78%
PPAR gamma	+	0.6934	69.34%
Honey bee toxicity	-	0.6977	69.77%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6055	60.55%
Fish aquatic toxicity	+	0.8242	82.42%

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	99.58%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.51%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.21%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.63%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.17%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.86%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.72%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.45%	97.09%
CHEMBL3194	P02766	Transthyretin	90.02%	90.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.24%	95.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.62%	86.92%
CHEMBL4208	P20618	Proteasome component C5	85.61%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.59%	94.45%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.38%	95.83%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.75%	97.28%
CHEMBL226	P30542	Adenosine A1 receptor	81.26%	95.93%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.13%	92.62%

Plants that contains it

• Simmondsia chinensis

Cross-Links

• PubChem: 101993518
• LOTUS: LTS0106679
• wikiData: Q104403284