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

Details

• Internal ID: ff5ad933-93b3-427e-93d4-95a7a92f3511
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)O[C@H]2[C@@H]3C=CO[C@H]([C@@H]3[C@@]4([C@H]2O4)CO)O[C@H]5[C@H](C([C@H](C(O5)O)O)O)O)O
• InChI: InChI=1S/C24H28O13/c1-32-13-8-10(2-4-12(13)26)3-5-14(27)34-19-11-6-7-33-22(15(11)24(9-25)20(19)37-24)36-23-18(30)16(28)17(29)21(31)35-23/h2-8,11,15-23,25-26,28-31H,9H2,1H3/b5-3+/t11-,15-,16?,17-,18+,19+,20+,21?,22+,23+,24-/m1/s1
• InChI Key: GAPFSCDHSVFRFR-JGEIWRCJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₁₃
• Molecular Weight: 524.50 g/mol
• Exact Mass: 524.15299094 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -1.65
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8305	83.05%
Caco-2	-	0.9047	90.47%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6027	60.27%
OATP2B1 inhibitior	-	0.8514	85.14%
OATP1B1 inhibitior	+	0.8406	84.06%
OATP1B3 inhibitior	+	0.9545	95.45%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.5572	55.72%
P-glycoprotein inhibitior	-	0.6510	65.10%
P-glycoprotein substrate	-	0.5474	54.74%
CYP3A4 substrate	+	0.6844	68.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8592	85.92%
CYP3A4 inhibition	-	0.6993	69.93%
CYP2C9 inhibition	-	0.8585	85.85%
CYP2C19 inhibition	-	0.6704	67.04%
CYP2D6 inhibition	-	0.8631	86.31%
CYP1A2 inhibition	-	0.8361	83.61%
CYP2C8 inhibition	+	0.7399	73.99%
CYP inhibitory promiscuity	-	0.6468	64.68%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5651	56.51%
Eye corrosion	-	0.9842	98.42%
Eye irritation	-	0.9424	94.24%
Skin irritation	-	0.7534	75.34%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4435	44.35%
Micronuclear	+	0.5833	58.33%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.7148	71.48%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8085	80.85%
Acute Oral Toxicity (c)	III	0.5944	59.44%
Estrogen receptor binding	+	0.6680	66.80%
Androgen receptor binding	+	0.5287	52.87%
Thyroid receptor binding	+	0.5981	59.81%
Glucocorticoid receptor binding	+	0.5804	58.04%
Aromatase binding	+	0.5335	53.35%
PPAR gamma	+	0.7650	76.50%
Honey bee toxicity	-	0.7576	75.76%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.6892	68.92%

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	99.73%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.48%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.44%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.42%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.73%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.05%	96.00%
CHEMBL3194	P02766	Transthyretin	89.83%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.97%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.72%	94.45%
CHEMBL4208	P20618	Proteasome component C5	88.72%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.71%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.23%	92.94%
CHEMBL3401	O75469	Pregnane X receptor	85.18%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.73%	92.62%
CHEMBL1951	P21397	Monoamine oxidase A	82.54%	91.49%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.04%	91.07%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.15%	86.92%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.01%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.89%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.59%	96.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.24%	96.95%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.19%	94.08%

Plants that contains it

• Catalpa ovata

Cross-Links

• PubChem: 163185287
• LOTUS: LTS0166272
• wikiData: Q105005549