[(2R,3S,4S,5R,6R)-6-[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: fc9ca0e2-0a60-4e54-a326-6cb64ea57916
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(C(O2)OC3(C(C(C(O3)CO)O)O)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)O[C@@]3([C@H]([C@@H]([C@H](O3)CO)O)O)CO)O)O)O)O
• InChI: InChI=1S/C22H30O14/c1-32-12-6-10(2-4-11(12)25)3-5-15(26)33-8-14-16(27)18(29)19(30)21(34-14)36-22(9-24)20(31)17(28)13(7-23)35-22/h2-6,13-14,16-21,23-25,27-31H,7-9H2,1H3/b5-3+/t13-,14-,16-,17-,18+,19-,20+,21-,22-/m1/s1
• InChI Key: XMBZZLUIFFOAHR-HNDQWBAUSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₁₄
• Molecular Weight: 518.50 g/mol
• Exact Mass: 518.16355563 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -3.42
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

• 118230-77-6
• [(2R,3S,4S,5R,6R)-6-[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7383	73.83%
Caco-2	-	0.9162	91.62%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7601	76.01%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.8787	87.87%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6918	69.18%
P-glycoprotein inhibitior	-	0.7210	72.10%
P-glycoprotein substrate	-	0.7853	78.53%
CYP3A4 substrate	+	0.6242	62.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8593	85.93%
CYP3A4 inhibition	-	0.8192	81.92%
CYP2C9 inhibition	-	0.8331	83.31%
CYP2C19 inhibition	-	0.7423	74.23%
CYP2D6 inhibition	-	0.8953	89.53%
CYP1A2 inhibition	-	0.8898	88.98%
CYP2C8 inhibition	+	0.6832	68.32%
CYP inhibitory promiscuity	-	0.5905	59.05%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6227	62.27%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9545	95.45%
Skin irritation	-	0.8374	83.74%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3888	38.88%
Micronuclear	-	0.6226	62.26%
Hepatotoxicity	-	0.9000	90.00%
skin sensitisation	-	0.8039	80.39%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.9020	90.20%
Acute Oral Toxicity (c)	III	0.7020	70.20%
Estrogen receptor binding	+	0.7262	72.62%
Androgen receptor binding	+	0.5658	56.58%
Thyroid receptor binding	+	0.5350	53.50%
Glucocorticoid receptor binding	-	0.4898	48.98%
Aromatase binding	+	0.6214	62.14%
PPAR gamma	+	0.6883	68.83%
Honey bee toxicity	-	0.7625	76.25%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.7963	79.63%

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	99.56%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.30%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.17%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.72%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.11%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.76%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	92.51%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.64%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	89.72%	94.73%
CHEMBL3194	P02766	Transthyretin	89.56%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.98%	97.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.77%	95.83%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.63%	85.14%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.58%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.12%	95.89%
CHEMBL4208	P20618	Proteasome component C5	81.57%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.33%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.09%	92.62%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.07%	89.62%

Plants that contains it

• Lilium speciosum

Cross-Links

• PubChem: 6443651
• LOTUS: LTS0004795
• wikiData: Q105330631