[2-[2-(Cyanomethylidene)-3,5-dihydroxy-4-methoxycyclohexyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: ebfe14df-ecc3-4624-af0e-c2bc6704afcc
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [2-[2-(cyanomethylidene)-3,5-dihydroxy-4-methoxycyclohexyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1C(CC(C(=CC#N)C1O)OC2C(C(C(C(O2)CO)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)OC)O
• SMILES (Isomeric): COC1C(CC(C(=CC#N)C1O)OC2C(C(C(C(O2)CO)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)OC)O
• InChI: InChI=1S/C25H31NO12/c1-34-17-9-12(3-5-14(17)28)4-6-19(30)38-24-22(33)21(32)18(11-27)37-25(24)36-16-10-15(29)23(35-2)20(31)13(16)7-8-26/h3-7,9,15-16,18,20-25,27-29,31-33H,10-11H2,1-2H3
• InChI Key: KZBHGKPXLHDZDW-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₁NO₁₂
• Molecular Weight: 537.50 g/mol
• Exact Mass: 537.18462542 g/mol
• Topological Polar Surface Area (TPSA): 208.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.26
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4621	46.21%
Caco-2	-	0.8938	89.38%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5339	53.39%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.8438	84.38%
OATP1B3 inhibitior	+	0.9564	95.64%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6091	60.91%
P-glycoprotein inhibitior	-	0.5340	53.40%
P-glycoprotein substrate	-	0.5433	54.33%
CYP3A4 substrate	+	0.6668	66.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8515	85.15%
CYP3A4 inhibition	-	0.7016	70.16%
CYP2C9 inhibition	-	0.7785	77.85%
CYP2C19 inhibition	-	0.8011	80.11%
CYP2D6 inhibition	-	0.8290	82.90%
CYP1A2 inhibition	-	0.7120	71.20%
CYP2C8 inhibition	+	0.6638	66.38%
CYP inhibitory promiscuity	-	0.5980	59.80%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7621	76.21%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9382	93.82%
Skin irritation	-	0.7994	79.94%
Skin corrosion	-	0.9562	95.62%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7754	77.54%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	-	0.6716	67.16%
skin sensitisation	-	0.7883	78.83%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.9404	94.04%
Acute Oral Toxicity (c)	III	0.6486	64.86%
Estrogen receptor binding	+	0.7811	78.11%
Androgen receptor binding	-	0.5136	51.36%
Thyroid receptor binding	+	0.5593	55.93%
Glucocorticoid receptor binding	+	0.5545	55.45%
Aromatase binding	+	0.5229	52.29%
PPAR gamma	+	0.6638	66.38%
Honey bee toxicity	-	0.6991	69.91%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5955	59.55%
Fish aquatic toxicity	-	0.3753	37.53%

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	99.61%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.53%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.47%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.43%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.40%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.82%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.04%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.44%	97.09%
CHEMBL3194	P02766	Transthyretin	90.21%	90.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.12%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.10%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.49%	89.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.69%	86.92%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.63%	95.83%
CHEMBL4208	P20618	Proteasome component C5	84.56%	90.00%
CHEMBL226	P30542	Adenosine A1 receptor	84.00%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.17%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.10%	92.62%
CHEMBL5255	O00206	Toll-like receptor 4	80.16%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.13%	95.89%

Plants that contains it

• Simmondsia chinensis

Cross-Links

• PubChem: 85104500
• LOTUS: LTS0045594
• wikiData: Q105148062