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

Details

• Internal ID: 87058d03-4eaf-40b0-a19c-6c3e56f5aba8
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4S,5R,6R)-2-[(1R,2E,3S,4R,5S)-2-(cyanomethylidene)-3-hydroxy-4,5-dimethoxycyclohexyl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-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)OC(=O)C=CC3=CC(=C(C=C3)O)OC)O
• 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)OC(=O)/C=C/C3=CC(=C(C=C3)O)OC)O
• InChI: InChI=1S/C26H33NO12/c1-34-17-10-13(4-6-15(17)29)5-7-20(30)39-25-22(32)19(12-28)38-26(23(25)33)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: FEUUHPJKQACSKU-YIJSCCIGSA-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	+	0.7604	76.04%
Caco-2	-	0.8807	88.07%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.5363	53.63%
OATP2B1 inhibitior	-	0.8604	86.04%
OATP1B1 inhibitior	+	0.8577	85.77%
OATP1B3 inhibitior	+	0.9301	93.01%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6633	66.33%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.5000	50.00%
CYP3A4 substrate	+	0.6816	68.16%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.8494	84.94%
CYP3A4 inhibition	-	0.6695	66.95%
CYP2C9 inhibition	-	0.6428	64.28%
CYP2C19 inhibition	-	0.5985	59.85%
CYP2D6 inhibition	-	0.7911	79.11%
CYP1A2 inhibition	-	0.5809	58.09%
CYP2C8 inhibition	+	0.6935	69.35%
CYP inhibitory promiscuity	+	0.6962	69.62%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9728	97.28%
Carcinogenicity (trinary)	Non-required	0.7643	76.43%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9409	94.09%
Skin irritation	-	0.7985	79.85%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	-	0.5764	57.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.3981	39.81%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8284	82.84%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8805	88.05%
Acute Oral Toxicity (c)	III	0.5815	58.15%
Estrogen receptor binding	+	0.8031	80.31%
Androgen receptor binding	-	0.5068	50.68%
Thyroid receptor binding	+	0.6026	60.26%
Glucocorticoid receptor binding	+	0.6871	68.71%
Aromatase binding	+	0.5540	55.40%
PPAR gamma	+	0.6888	68.88%
Honey bee toxicity	-	0.6939	69.39%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5755	57.55%
Fish aquatic toxicity	+	0.7996	79.96%

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	99.70%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.19%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.04%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.92%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.06%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.02%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.15%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.83%	99.17%
CHEMBL3194	P02766	Transthyretin	88.76%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.90%	86.92%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.96%	95.83%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.59%	92.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.92%	95.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.18%	97.28%
CHEMBL4208	P20618	Proteasome component C5	82.04%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.40%	94.45%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	80.62%	97.03%

Plants that contains it

• Simmondsia chinensis

Cross-Links

• PubChem: 101993517
• LOTUS: LTS0269962
• wikiData: Q104994210