[(1S)-1-[(2S,5R)-5-[(S)-hydroxy-[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]oxolan-2-yl]ethyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: 95a236fc-96fa-40e6-af38-6fdd1a5acecd
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(1S)-1-[(2S,5R)-5-[(S)-hydroxy-[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]oxolan-2-yl]ethyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC(C1CCC(O1)C(C2CC=CC(=O)O2)O)OC(=O)C=CC3=CC(=C(C=C3)O)O
• SMILES (Isomeric): C[C@@H]([C@@H]1CC[C@@H](O1)[C@@H]([C@H]2CC=CC(=O)O2)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O
• InChI: InChI=1S/C21H24O8/c1-12(27-20(25)10-6-13-5-7-14(22)15(23)11-13)16-8-9-18(28-16)21(26)17-3-2-4-19(24)29-17/h2,4-7,10-12,16-18,21-23,26H,3,8-9H2,1H3/b10-6+/t12-,16-,17+,18+,21+/m0/s1
• InChI Key: QMGPOYYFOFDFEO-JPYSVIHJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₈
• Molecular Weight: 404.40 g/mol
• Exact Mass: 404.14711772 g/mol
• Topological Polar Surface Area (TPSA): 123.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.82
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8254	82.54%
Caco-2	-	0.7487	74.87%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.9026	90.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9165	91.65%
OATP1B3 inhibitior	+	0.8942	89.42%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.6343	63.43%
P-glycoprotein inhibitior	-	0.6583	65.83%
P-glycoprotein substrate	-	0.6076	60.76%
CYP3A4 substrate	+	0.6189	61.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8749	87.49%
CYP3A4 inhibition	-	0.8823	88.23%
CYP2C9 inhibition	-	0.7104	71.04%
CYP2C19 inhibition	-	0.5773	57.73%
CYP2D6 inhibition	-	0.9115	91.15%
CYP1A2 inhibition	+	0.5276	52.76%
CYP2C8 inhibition	+	0.4433	44.33%
CYP inhibitory promiscuity	-	0.8346	83.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.4974	49.74%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9485	94.85%
Skin irritation	-	0.6871	68.71%
Skin corrosion	-	0.8859	88.59%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4089	40.89%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8232	82.32%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.5541	55.41%
Acute Oral Toxicity (c)	III	0.3635	36.35%
Estrogen receptor binding	+	0.6995	69.95%
Androgen receptor binding	+	0.6567	65.67%
Thyroid receptor binding	-	0.5095	50.95%
Glucocorticoid receptor binding	+	0.6121	61.21%
Aromatase binding	-	0.5313	53.13%
PPAR gamma	+	0.6143	61.43%
Honey bee toxicity	-	0.8352	83.52%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9793	97.93%

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	99.25%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.73%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.22%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.90%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.22%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.91%	97.09%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	90.69%	92.88%
CHEMBL3194	P02766	Transthyretin	90.33%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	90.14%	91.49%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.94%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.50%	99.15%
CHEMBL4208	P20618	Proteasome component C5	88.07%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.55%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.01%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.13%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.96%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.93%	95.89%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	83.57%	83.10%
CHEMBL4015	P41597	C-C chemokine receptor type 2	83.44%	98.57%
CHEMBL321	P14780	Matrix metalloproteinase 9	83.01%	92.12%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.80%	91.07%
CHEMBL3401	O75469	Pregnane X receptor	81.95%	94.73%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.90%	90.24%
CHEMBL340	P08684	Cytochrome P450 3A4	81.19%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.79%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.71%	100.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.54%	93.40%

Plants that contains it

• Hyptis brevipes

Cross-Links

• PubChem: 137661365
• LOTUS: LTS0185606
• wikiData: Q103815882