[(2R,3S,4S,5R,6S)-6-[[(1S,2R,4S,5S,6R,10S)-5,6-dihydroxy-2-methyl-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (Z)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 4f3dd2d3-d795-45ae-96b5-65df445feeb6
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[[(1S,2R,4S,5S,6R,10S)-5,6-dihydroxy-2-methyl-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (Z)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC12C3C(OC=CC3(C(C1O2)O)O)OC4C(C(C(C(O4)COC(=O)C=CC5=CC=C(C=C5)O)O)O)O
• SMILES (Isomeric): C[C@@]12[C@H]3[C@@H](OC=C[C@@]3([C@H]([C@@H]1O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)/C=C\C5=CC=C(C=C5)O)O)O)O
• InChI: InChI=1S/C24H28O12/c1-23-18-22(32-9-8-24(18,31)19(30)20(23)36-23)35-21-17(29)16(28)15(27)13(34-21)10-33-14(26)7-4-11-2-5-12(25)6-3-11/h2-9,13,15-22,25,27-31H,10H2,1H3/b7-4-/t13-,15-,16+,17-,18-,19+,20+,21+,22+,23-,24-/m1/s1
• InChI Key: PRYABGKDJFUETA-SWTHUAQRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₁₂
• Molecular Weight: 508.50 g/mol
• Exact Mass: 508.15807632 g/mol
• Topological Polar Surface Area (TPSA): 188.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.48
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7244	72.44%
Caco-2	-	0.8704	87.04%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.7050	70.50%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.8228	82.28%
OATP1B3 inhibitior	+	0.9510	95.10%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6054	60.54%
P-glycoprotein inhibitior	-	0.6578	65.78%
P-glycoprotein substrate	-	0.6437	64.37%
CYP3A4 substrate	+	0.6885	68.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8785	87.85%
CYP3A4 inhibition	-	0.8995	89.95%
CYP2C9 inhibition	-	0.8750	87.50%
CYP2C19 inhibition	-	0.7768	77.68%
CYP2D6 inhibition	-	0.8942	89.42%
CYP1A2 inhibition	-	0.8465	84.65%
CYP2C8 inhibition	+	0.6767	67.67%
CYP inhibitory promiscuity	-	0.6974	69.74%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5102	51.02%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9402	94.02%
Skin irritation	-	0.7381	73.81%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3747	37.47%
Micronuclear	+	0.5792	57.92%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.7749	77.49%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6072	60.72%
Acute Oral Toxicity (c)	III	0.4749	47.49%
Estrogen receptor binding	+	0.6294	62.94%
Androgen receptor binding	+	0.6878	68.78%
Thyroid receptor binding	+	0.5390	53.90%
Glucocorticoid receptor binding	+	0.5861	58.61%
Aromatase binding	-	0.4925	49.25%
PPAR gamma	+	0.6928	69.28%
Honey bee toxicity	-	0.7778	77.78%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6255	62.55%
Fish aquatic toxicity	+	0.8723	87.23%

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	98.12%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.16%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.22%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.55%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.75%	96.00%
CHEMBL226	P30542	Adenosine A1 receptor	90.09%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.97%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	89.75%	94.73%
CHEMBL221	P23219	Cyclooxygenase-1	87.49%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.05%	99.17%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.98%	89.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.60%	95.56%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	84.79%	93.10%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.75%	97.28%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.88%	97.09%
CHEMBL3194	P02766	Transthyretin	82.31%	90.71%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.05%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.13%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	80.13%	91.49%

Plants that contains it

• Harpagophytum procumbens

Cross-Links

• PubChem: 162990977
• LOTUS: LTS0125248
• wikiData: Q105213994