[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[2-[(2R)-2,4,6-trimethyl-3-oxo-1,2-dihydroinden-5-yl]ethoxy]oxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 9632f06d-46d3-4c94-b5d8-7b8fbcb2c3f6
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[2-[(2R)-2,4,6-trimethyl-3-oxo-1,2-dihydroinden-5-yl]ethoxy]oxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1CC2=C(C1=O)C(=C(C(=C2)C)CCOC3C(C(C(C(O3)CO)OC(=O)C=CC4=CC=C(C=C4)O)O)O)C
• SMILES (Isomeric): C[C@@H]1CC2=C(C1=O)C(=C(C(=C2)C)CCO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)OC(=O)/C=C/C4=CC=C(C=C4)O)O)O)C
• InChI: InChI=1S/C29H34O9/c1-15-12-19-13-16(2)25(33)24(19)17(3)21(15)10-11-36-29-27(35)26(34)28(22(14-30)37-29)38-23(32)9-6-18-4-7-20(31)8-5-18/h4-9,12,16,22,26-31,34-35H,10-11,13-14H2,1-3H3/b9-6+/t16-,22-,26-,27-,28-,29-/m1/s1
• InChI Key: DGOOMWFMTZLGGS-PBRNXLBUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₄O₉
• Molecular Weight: 526.60 g/mol
• Exact Mass: 526.22028266 g/mol
• Topological Polar Surface Area (TPSA): 143.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.01
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

• CHEMBL256094

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7337	73.37%
Caco-2	-	0.8354	83.54%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7524	75.24%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.8421	84.21%
OATP1B3 inhibitior	+	0.9076	90.76%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5676	56.76%
P-glycoprotein inhibitior	-	0.4526	45.26%
P-glycoprotein substrate	-	0.5273	52.73%
CYP3A4 substrate	+	0.6765	67.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8876	88.76%
CYP3A4 inhibition	-	0.8848	88.48%
CYP2C9 inhibition	-	0.7654	76.54%
CYP2C19 inhibition	-	0.7156	71.56%
CYP2D6 inhibition	-	0.9246	92.46%
CYP1A2 inhibition	+	0.6020	60.20%
CYP2C8 inhibition	+	0.6631	66.31%
CYP inhibitory promiscuity	-	0.7837	78.37%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6756	67.56%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9366	93.66%
Skin irritation	-	0.7799	77.99%
Skin corrosion	-	0.9449	94.49%
Ames mutagenesis	-	0.5854	58.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.6824	68.24%
skin sensitisation	-	0.8793	87.93%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.9095	90.95%
Acute Oral Toxicity (c)	III	0.5333	53.33%
Estrogen receptor binding	+	0.7292	72.92%
Androgen receptor binding	+	0.6921	69.21%
Thyroid receptor binding	-	0.5333	53.33%
Glucocorticoid receptor binding	+	0.6393	63.93%
Aromatase binding	+	0.5401	54.01%
PPAR gamma	-	0.5526	55.26%
Honey bee toxicity	-	0.7831	78.31%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9807	98.07%

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	99.20%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.28%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.05%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.82%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.89%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	92.46%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.99%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.27%	97.09%
CHEMBL4208	P20618	Proteasome component C5	89.94%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.14%	96.09%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	88.26%	85.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	88.16%	91.71%
CHEMBL3194	P02766	Transthyretin	88.01%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.65%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.11%	96.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.76%	97.36%
CHEMBL1951	P21397	Monoamine oxidase A	82.18%	91.49%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.79%	91.07%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.43%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	81.40%	92.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.42%	97.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.15%	96.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.12%	99.15%

Plants that contains it

• Pteris multifida
• Swietenia mahagoni

Cross-Links

• PubChem: 24800715
• NPASS: NPC257847
• ChEMBL: CHEMBL256094
• LOTUS: LTS0059100
• wikiData: Q104978947