[(2R,3S,4S,5S)-5-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: 115fcbc5-4ae0-434c-8247-e3c601bc455a
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3S,4S,5S)-5-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2(C(C(C(O2)COC(=O)C=CC3=CC(=C(C=C3)O)OC)O)O)CO)O)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)COC(=O)/C=C/C3=CC(=C(C=C3)O)OC)O)O)CO)O)O)O
• InChI: InChI=1S/C24H32O15/c1-11(26)35-8-15-18(29)20(31)21(32)23(37-15)39-24(10-25)22(33)19(30)16(38-24)9-36-17(28)6-4-12-3-5-13(27)14(7-12)34-2/h3-7,15-16,18-23,25,27,29-33H,8-10H2,1-2H3/b6-4+/t15-,16-,18-,19-,20+,21-,22+,23-,24+/m1/s1
• InChI Key: ZIUKDKVKRXUKAP-LUFLMYNCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₂O₁₅
• Molecular Weight: 560.50 g/mol
• Exact Mass: 560.17412031 g/mol
• Topological Polar Surface Area (TPSA): 231.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.85
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6882	68.82%
Caco-2	-	0.8994	89.94%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7168	71.68%
OATP2B1 inhibitior	-	0.8608	86.08%
OATP1B1 inhibitior	+	0.8798	87.98%
OATP1B3 inhibitior	+	0.9497	94.97%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6682	66.82%
P-glycoprotein inhibitior	-	0.5678	56.78%
P-glycoprotein substrate	-	0.7425	74.25%
CYP3A4 substrate	+	0.6370	63.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8706	87.06%
CYP3A4 inhibition	-	0.8250	82.50%
CYP2C9 inhibition	-	0.8579	85.79%
CYP2C19 inhibition	-	0.8248	82.48%
CYP2D6 inhibition	-	0.9204	92.04%
CYP1A2 inhibition	-	0.8757	87.57%
CYP2C8 inhibition	+	0.7053	70.53%
CYP inhibitory promiscuity	-	0.7799	77.99%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7070	70.70%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9393	93.93%
Skin irritation	-	0.8301	83.01%
Skin corrosion	-	0.9500	95.00%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4005	40.05%
Micronuclear	-	0.6126	61.26%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8179	81.79%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8710	87.10%
Acute Oral Toxicity (c)	III	0.6242	62.42%
Estrogen receptor binding	+	0.7622	76.22%
Androgen receptor binding	+	0.5929	59.29%
Thyroid receptor binding	+	0.5509	55.09%
Glucocorticoid receptor binding	+	0.6045	60.45%
Aromatase binding	+	0.6226	62.26%
PPAR gamma	+	0.6499	64.99%
Honey bee toxicity	-	0.7620	76.20%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9309	93.09%

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	99.70%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.55%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.08%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	96.88%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.47%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.27%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	92.45%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.89%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.80%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.55%	85.14%
CHEMBL3194	P02766	Transthyretin	86.98%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.43%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.84%	89.62%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.39%	96.90%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.80%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.60%	95.89%
CHEMBL4208	P20618	Proteasome component C5	80.56%	90.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.37%	96.95%

Plants that contains it

• Ageratina adenophora
• Boehmeria nivea
• Crotalaria micans
• Croton poilanei
• Dasymaschalon sootepense
• Dictyoloma vandellianum
• Euonymus sachalinensis
• Felicia erigeroides
• Flueggea virosa subsp. melanthesoides
• Guatteria megalophylla
• Lupinus paniculatus
• Lycoris traubii
• Lygodium flexuosum
• Panax ginseng
• Saccharum spontaneum
• Smilax bracteata
• Strychnos staudtii
• Tsuga mertensiana

Cross-Links

• PubChem: 11092923
• NPASS: NPC87322
• LOTUS: LTS0194893
• wikiData: Q105377499