[(2S,5R)-2,5-dihydroxycyclopentyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: f473f480-e85f-4c25-b53b-49e654b316ac
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2S,5R)-2,5-dihydroxycyclopentyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• InChI: InChI=1S/C14H16O6/c15-9-3-1-8(7-12(9)18)2-6-13(19)20-14-10(16)4-5-11(14)17/h1-3,6-7,10-11,14-18H,4-5H2/b6-2+/t10-,11+,14?
• InChI Key: XYGMVEGBGQSULF-RQEVDEIRSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₆O₆
• Molecular Weight: 280.27 g/mol
• Exact Mass: 280.09468823 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.54
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8739	87.39%
Caco-2	-	0.7386	73.86%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7373	73.73%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9654	96.54%
OATP1B3 inhibitior	+	0.9551	95.51%
MATE1 inhibitior	-	0.5400	54.00%
OCT2 inhibitior	-	0.9338	93.38%
BSEP inhibitior	-	0.7978	79.78%
P-glycoprotein inhibitior	-	0.9458	94.58%
P-glycoprotein substrate	-	0.9482	94.82%
CYP3A4 substrate	-	0.5334	53.34%
CYP2C9 substrate	-	0.7965	79.65%
CYP2D6 substrate	-	0.8337	83.37%
CYP3A4 inhibition	-	0.8953	89.53%
CYP2C9 inhibition	-	0.8611	86.11%
CYP2C19 inhibition	-	0.7996	79.96%
CYP2D6 inhibition	-	0.9263	92.63%
CYP1A2 inhibition	-	0.6558	65.58%
CYP2C8 inhibition	-	0.6246	62.46%
CYP inhibitory promiscuity	-	0.9160	91.60%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6265	62.65%
Eye corrosion	-	0.9767	97.67%
Eye irritation	-	0.6307	63.07%
Skin irritation	-	0.5217	52.17%
Skin corrosion	-	0.8832	88.32%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7900	79.00%
Micronuclear	+	0.5259	52.59%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	+	0.5508	55.08%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.9089	90.89%
Acute Oral Toxicity (c)	III	0.6370	63.70%
Estrogen receptor binding	+	0.7473	74.73%
Androgen receptor binding	+	0.7413	74.13%
Thyroid receptor binding	+	0.5295	52.95%
Glucocorticoid receptor binding	+	0.5402	54.02%
Aromatase binding	-	0.6185	61.85%
PPAR gamma	+	0.6786	67.86%
Honey bee toxicity	-	0.8649	86.49%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5455	54.55%
Fish aquatic toxicity	+	0.8890	88.90%

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	99.47%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.95%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.42%	97.09%
CHEMBL3194	P02766	Transthyretin	91.03%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.62%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.67%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.66%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.10%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.79%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.25%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.89%	99.15%
CHEMBL4040	P28482	MAP kinase ERK2	82.60%	83.82%
CHEMBL4208	P20618	Proteasome component C5	82.42%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.50%	91.19%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.10%	96.12%

Plants that contains it

• Prunus cerasus

Cross-Links

• PubChem: 9903815
• LOTUS: LTS0263198
• wikiData: Q105344475