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

Details

• Internal ID: 222dd933-a640-4f04-8aaf-327bb9eac6ed
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2S,3R,4R,5R,6S)-5-acetyloxy-4-hydroxy-2-[[(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl]oxy]-6-methyloxan-3-yl] (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)OC(=O)C=CC6=CC(=C(C=C6)OC)O)O)OC(=O)C
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)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@H]([C@@H]([C@H](O5)CO)O)O)O)OC(=O)/C=C/C6=CC(=C(C=C6)OC)O)O)OC(=O)C
• InChI: InChI=1S/C33H42O18/c1-13-26(46-14(2)36)25(42)28(48-20(38)7-5-15-4-6-18(43-3)17(37)10-15)32(45-13)49-27-16-8-9-44-30(21(16)33(12-35)29(27)51-33)50-31-24(41)23(40)22(39)19(11-34)47-31/h4-10,13,16,19,21-32,34-35,37,39-42H,11-12H2,1-3H3/b7-5+/t13-,16+,19+,21+,22+,23-,24+,25+,26-,27-,28+,29-,30-,31-,32-,33+/m0/s1
• InChI Key: XYCYUUSEIAGVKO-UYMHYVCLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₂O₁₈
• Molecular Weight: 726.70 g/mol
• Exact Mass: 726.23711449 g/mol
• Topological Polar Surface Area (TPSA): 262.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -2.19
• H-Bond Acceptor: 18
• H-Bond Donor: 7
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5644	56.44%
Caco-2	-	0.8824	88.24%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.4986	49.86%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.8214	82.14%
OATP1B3 inhibitior	+	0.9529	95.29%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4809	48.09%
P-glycoprotein inhibitior	+	0.6415	64.15%
P-glycoprotein substrate	+	0.6466	64.66%
CYP3A4 substrate	+	0.7113	71.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8719	87.19%
CYP3A4 inhibition	-	0.8834	88.34%
CYP2C9 inhibition	-	0.8647	86.47%
CYP2C19 inhibition	-	0.8166	81.66%
CYP2D6 inhibition	-	0.9170	91.70%
CYP1A2 inhibition	-	0.8564	85.64%
CYP2C8 inhibition	+	0.7448	74.48%
CYP inhibitory promiscuity	-	0.7989	79.89%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5977	59.77%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9226	92.26%
Skin irritation	-	0.7954	79.54%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3807	38.07%
Micronuclear	+	0.5333	53.33%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8142	81.42%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7874	78.74%
Acute Oral Toxicity (c)	III	0.5060	50.60%
Estrogen receptor binding	+	0.7333	73.33%
Androgen receptor binding	+	0.5212	52.12%
Thyroid receptor binding	-	0.4875	48.75%
Glucocorticoid receptor binding	+	0.6310	63.10%
Aromatase binding	-	0.5408	54.08%
PPAR gamma	+	0.7214	72.14%
Honey bee toxicity	-	0.6707	67.07%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8062	80.62%

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	99.58%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.58%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.14%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.80%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.61%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.53%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.57%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	94.72%	91.49%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.48%	92.94%
CHEMBL1937	Q92769	Histone deacetylase 2	89.92%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.77%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.74%	99.17%
CHEMBL2581	P07339	Cathepsin D	87.94%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.50%	86.92%
CHEMBL4208	P20618	Proteasome component C5	87.45%	90.00%
CHEMBL3194	P02766	Transthyretin	86.95%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.68%	97.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.20%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	85.04%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.79%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.56%	95.50%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	80.94%	98.00%

Plants that contains it

• Premna microphylla

Cross-Links

• PubChem: 21629984
• LOTUS: LTS0250760
• wikiData: Q105274323