[(2R,3S,4S)-4-hydroxy-2-methyl-5-oxooxolan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: 08f98399-5dff-4632-98cc-d95a95cac149
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3S,4S)-4-hydroxy-2-methyl-5-oxooxolan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• InChI: InChI=1S/C14H14O7/c1-7-13(12(18)14(19)20-7)21-11(17)5-3-8-2-4-9(15)10(16)6-8/h2-7,12-13,15-16,18H,1H3/b5-3+/t7-,12+,13-/m1/s1
• InChI Key: GAKVKJFTNYQYDY-KOAAFIIWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₇
• Molecular Weight: 294.26 g/mol
• Exact Mass: 294.07395278 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.33
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• CHEMBL486185

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9377	93.77%
Caco-2	-	0.6338	63.38%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8188	81.88%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9149	91.49%
OATP1B3 inhibitior	+	0.9636	96.36%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7423	74.23%
P-glycoprotein inhibitior	-	0.8828	88.28%
P-glycoprotein substrate	-	0.8799	87.99%
CYP3A4 substrate	+	0.5092	50.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8699	86.99%
CYP3A4 inhibition	-	0.8908	89.08%
CYP2C9 inhibition	-	0.7043	70.43%
CYP2C19 inhibition	-	0.5995	59.95%
CYP2D6 inhibition	-	0.9577	95.77%
CYP1A2 inhibition	-	0.5235	52.35%
CYP2C8 inhibition	-	0.6560	65.60%
CYP inhibitory promiscuity	-	0.6602	66.02%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8894	88.94%
Carcinogenicity (trinary)	Non-required	0.4730	47.30%
Eye corrosion	-	0.9217	92.17%
Eye irritation	-	0.7459	74.59%
Skin irritation	-	0.5551	55.51%
Skin corrosion	-	0.8067	80.67%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7893	78.93%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.5351	53.51%
skin sensitisation	-	0.6601	66.01%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8241	82.41%
Acute Oral Toxicity (c)	III	0.5791	57.91%
Estrogen receptor binding	-	0.4747	47.47%
Androgen receptor binding	+	0.7095	70.95%
Thyroid receptor binding	-	0.6790	67.90%
Glucocorticoid receptor binding	-	0.5871	58.71%
Aromatase binding	-	0.7026	70.26%
PPAR gamma	-	0.5896	58.96%
Honey bee toxicity	-	0.8327	83.27%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9779	97.79%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.52%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.48%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.37%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.51%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.41%	89.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	89.33%	80.78%
CHEMBL3194	P02766	Transthyretin	87.69%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	86.33%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.38%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.24%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.23%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.29%	99.23%

Plants that contains it

• Haplopteris anguste-elongata

Cross-Links

• PubChem: 11673743
• LOTUS: LTS0145301
• wikiData: Q105005460