[(2S,3S,4R,5R,6S)-5-acetyloxy-6-[[(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]-4-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy-2-methyloxan-3-yl] (E)-3-(4-methoxyphenyl)prop-2-enoate

Details

• Internal ID: a6626628-2c48-456a-baac-cc00ed24ca61
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
• IUPAC Name: [(2S,3S,4R,5R,6S)-5-acetyloxy-6-[[(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]-4-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy-2-methyloxan-3-yl] (E)-3-(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)OC(=O)C=CC6=CC=C(C=C6)OC)OC(=O)C=CC7=CC=C(C=C7)OC
• 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)OC(=O)/C=C/C6=CC=C(C=C6)OC)OC(=O)/C=C/C7=CC=C(C=C7)OC
• InChI: InChI=1S/C43H50O19/c1-21-35(58-29(47)15-9-23-5-11-25(52-3)12-6-23)37(59-30(48)16-10-24-7-13-26(53-4)14-8-24)38(56-22(2)46)42(55-21)60-36-27-17-18-54-40(31(27)43(20-45)39(36)62-43)61-41-34(51)33(50)32(49)28(19-44)57-41/h5-18,21,27-28,31-42,44-45,49-51H,19-20H2,1-4H3/b15-9+,16-10+/t21-,27+,28+,31+,32+,33-,34+,35-,36-,37+,38+,39-,40-,41-,42-,43+/m0/s1
• InChI Key: BUIPMVNSPLYJFB-WFSCQCABSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₅₀O₁₉
• Molecular Weight: 870.80 g/mol
• Exact Mass: 870.29462936 g/mol
• Topological Polar Surface Area (TPSA): 257.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 0.38
• H-Bond Acceptor: 19
• H-Bond Donor: 5
• Rotatable Bonds: 15

Synonyms

• ACon1_000902
• NCGC00169247-01
• BRD-K61320268-001-01-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5000	50.00%
Caco-2	-	0.8644	86.44%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5479	54.79%
OATP2B1 inhibitior	+	0.5560	55.60%
OATP1B1 inhibitior	+	0.8064	80.64%
OATP1B3 inhibitior	+	0.9519	95.19%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9273	92.73%
P-glycoprotein inhibitior	+	0.7558	75.58%
P-glycoprotein substrate	+	0.5349	53.49%
CYP3A4 substrate	+	0.7129	71.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8741	87.41%
CYP3A4 inhibition	-	0.8894	88.94%
CYP2C9 inhibition	-	0.8899	88.99%
CYP2C19 inhibition	-	0.8497	84.97%
CYP2D6 inhibition	-	0.9210	92.10%
CYP1A2 inhibition	-	0.8971	89.71%
CYP2C8 inhibition	+	0.6464	64.64%
CYP inhibitory promiscuity	-	0.8181	81.81%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5599	55.99%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9078	90.78%
Skin irritation	-	0.7954	79.54%
Skin corrosion	-	0.9421	94.21%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7896	78.96%
Micronuclear	+	0.5633	56.33%
Hepatotoxicity	-	0.7782	77.82%
skin sensitisation	-	0.8210	82.10%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.5899	58.99%
Acute Oral Toxicity (c)	III	0.4818	48.18%
Estrogen receptor binding	+	0.7863	78.63%
Androgen receptor binding	+	0.6100	61.00%
Thyroid receptor binding	+	0.6160	61.60%
Glucocorticoid receptor binding	+	0.7096	70.96%
Aromatase binding	+	0.5190	51.90%
PPAR gamma	+	0.7448	74.48%
Honey bee toxicity	-	0.6721	67.21%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8645	86.45%

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	99.41%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.16%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.49%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.26%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.18%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.91%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.21%	89.00%
CHEMBL4208	P20618	Proteasome component C5	90.32%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.19%	97.36%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	88.83%	87.67%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.82%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.75%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	86.37%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.16%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.86%	94.00%
CHEMBL2581	P07339	Cathepsin D	84.93%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.39%	94.45%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.80%	81.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.19%	97.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.49%	91.07%
CHEMBL226	P30542	Adenosine A1 receptor	80.29%	95.93%

Plants that contains it

• Scrophularia nodosa

Cross-Links

• PubChem: 10700832
• LOTUS: LTS0167285
• wikiData: Q104946123