[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-[[(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5R,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]-2-methyloxan-3-yl] (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

Details

• Internal ID: 99a8cd2f-f35a-4ae9-9ad9-fac1b167ae92
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-[[(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5R,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]-2-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)OC(=O)C)OC(=O)C=CC6=CC(=C(C=C6)OC)O
• 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)OC(=O)/C=C/C6=CC(=C(C=C6)OC)O
• InChI: InChI=1S/C35H44O19/c1-14-27(51-22(41)8-6-17-5-7-20(45-4)19(40)11-17)29(48-15(2)38)30(49-16(3)39)34(47-14)52-28-18-9-10-46-32(23(18)35(13-37)31(28)54-35)53-33-26(44)25(43)24(42)21(12-36)50-33/h5-11,14,18,21,23-34,36-37,40,42-44H,12-13H2,1-4H3/b8-6+/t14-,18-,21+,23+,24-,25-,26+,27-,28-,29+,30+,31-,32-,33-,34-,35+/m0/s1
• InChI Key: FYTGEKJFCXSGKK-YIMIRFLISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₄O₁₉
• Molecular Weight: 768.70 g/mol
• Exact Mass: 768.24767917 g/mol
• Topological Polar Surface Area (TPSA): 268.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.62
• H-Bond Acceptor: 19
• H-Bond Donor: 6
• Rotatable Bonds: 12

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	-	0.8711	87.11%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.4986	49.86%
OATP2B1 inhibitior	-	0.8566	85.66%
OATP1B1 inhibitior	+	0.8178	81.78%
OATP1B3 inhibitior	+	0.9529	95.29%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8267	82.67%
P-glycoprotein inhibitior	+	0.7344	73.44%
P-glycoprotein substrate	+	0.6302	63.02%
CYP3A4 substrate	+	0.7133	71.33%
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	+	0.7491	74.91%
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	-	0.9147	91.47%
Skin irritation	-	0.7954	79.54%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6906	69.06%
Micronuclear	+	0.5333	53.33%
Hepatotoxicity	-	0.8250	82.50%
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	-	0.7383	73.83%
Acute Oral Toxicity (c)	III	0.5060	50.60%
Estrogen receptor binding	+	0.8023	80.23%
Androgen receptor binding	+	0.5314	53.14%
Thyroid receptor binding	+	0.5554	55.54%
Glucocorticoid receptor binding	+	0.7133	71.33%
Aromatase binding	+	0.5544	55.44%
PPAR gamma	+	0.7603	76.03%
Honey bee toxicity	-	0.6644	66.44%
Biodegradation	-	0.8500	85.00%
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	99.65%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.42%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.95%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.18%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.71%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.61%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.62%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	94.18%	91.49%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.59%	92.94%
CHEMBL2581	P07339	Cathepsin D	88.96%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.77%	99.17%
CHEMBL1937	Q92769	Histone deacetylase 2	88.73%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.01%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.55%	95.89%
CHEMBL4208	P20618	Proteasome component C5	86.37%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	85.96%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.88%	97.36%
CHEMBL3194	P02766	Transthyretin	85.82%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.77%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.53%	86.92%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.79%	95.50%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	80.45%	98.00%

Plants that contains it

• Scrophularia nodosa

Cross-Links

• PubChem: 162875648
• LOTUS: LTS0212139
• wikiData: Q105004711