[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(1S,2S,4S,5S,6R,10S)-5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]oxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: a2af0f32-fa5d-4a7f-b322-61ebe8ec7982
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(1S,2S,4S,5S,6R,10S)-5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]oxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(C(O2)OC3C4C(C=CO3)C(C5C4(O5)CO)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@H]2[C@@H]([C@@H]([C@@H]([C@H](O2)O[C@H]3[C@H]4[C@@H](C=CO3)[C@@H]([C@H]5[C@@]4(O5)CO)O)O)O)O)O
• InChI: InChI=1S/C25H30O13/c1-33-14-8-11(2-4-13(14)27)3-5-16(28)35-9-15-19(30)20(31)21(32)24(36-15)37-23-17-12(6-7-34-23)18(29)22-25(17,10-26)38-22/h2-8,12,15,17-24,26-27,29-32H,9-10H2,1H3/b5-3+/t12-,15+,17-,18+,19+,20+,21+,22+,23+,24-,25-/m1/s1
• InChI Key: DPHFMUYFANVRJL-KLPNLWAHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₀O₁₃
• Molecular Weight: 538.50 g/mol
• Exact Mass: 538.16864101 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.61
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6435	64.35%
Caco-2	-	0.9013	90.13%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5653	56.53%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.8331	83.31%
OATP1B3 inhibitior	+	0.9676	96.76%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6063	60.63%
P-glycoprotein inhibitior	-	0.6012	60.12%
P-glycoprotein substrate	-	0.5774	57.74%
CYP3A4 substrate	+	0.6798	67.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8609	86.09%
CYP3A4 inhibition	-	0.8901	89.01%
CYP2C9 inhibition	-	0.8604	86.04%
CYP2C19 inhibition	-	0.7030	70.30%
CYP2D6 inhibition	-	0.8722	87.22%
CYP1A2 inhibition	-	0.8509	85.09%
CYP2C8 inhibition	+	0.7566	75.66%
CYP inhibitory promiscuity	-	0.7046	70.46%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5543	55.43%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9480	94.80%
Skin irritation	-	0.7812	78.12%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4030	40.30%
Micronuclear	+	0.5433	54.33%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.7891	78.91%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8814	88.14%
Acute Oral Toxicity (c)	III	0.5594	55.94%
Estrogen receptor binding	+	0.7156	71.56%
Androgen receptor binding	+	0.5474	54.74%
Thyroid receptor binding	-	0.5309	53.09%
Glucocorticoid receptor binding	-	0.4763	47.63%
Aromatase binding	+	0.5696	56.96%
PPAR gamma	+	0.6614	66.14%
Honey bee toxicity	-	0.7959	79.59%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.6878	68.78%

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	99.59%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.79%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.43%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.57%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	95.50%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.89%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.64%	95.56%
CHEMBL3194	P02766	Transthyretin	91.73%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.11%	99.17%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.70%	96.61%
CHEMBL3401	O75469	Pregnane X receptor	87.73%	94.73%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.13%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.84%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.58%	89.62%
CHEMBL4208	P20618	Proteasome component C5	85.71%	90.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.10%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.66%	95.89%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.66%	96.90%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.16%	86.92%

Plants that contains it

• Neopicrorhiza scrophulariiflora
• Scutellaria albida subsp. albida

Cross-Links

• PubChem: 162983203
• LOTUS: LTS0221744
• wikiData: Q104986497