[(2S,3S,4S,5R,6S)-4-acetyloxy-5-hydroxy-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]-2-methyloxan-3-yl] (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate

Details

• Internal ID: 0005429a-4a28-4fe5-9c99-6c364e316091
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2S,3S,4S,5R,6S)-4-acetyloxy-5-hydroxy-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]-2-methyloxan-3-yl] (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)O)OC(=O)C)OC(=O)C=CC6=CC(=C(C=C6)OC)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)O)OC(=O)C)OC(=O)/C=C/C6=CC(=C(C=C6)OC)OC
• InChI: InChI=1S/C34H44O18/c1-14-27(49-21(38)8-6-16-5-7-18(43-3)19(11-16)44-4)29(47-15(2)37)26(42)33(46-14)50-28-17-9-10-45-31(22(17)34(13-36)30(28)52-34)51-32-25(41)24(40)23(39)20(12-35)48-32/h5-11,14,17,20,22-33,35-36,39-42H,12-13H2,1-4H3/b8-6+/t14-,17+,20+,22+,23+,24-,25+,26+,27-,28-,29-,30-,31-,32-,33-,34+/m0/s1
• InChI Key: DHVIJZMBLVQPGZ-QBJJRHNXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₄O₁₈
• Molecular Weight: 740.70 g/mol
• Exact Mass: 740.25276455 g/mol
• Topological Polar Surface Area (TPSA): 251.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.89
• H-Bond Acceptor: 18
• 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	-	0.8718	87.18%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.4986	49.86%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	+	0.8213	82.13%
OATP1B3 inhibitior	+	0.9529	95.29%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8157	81.57%
P-glycoprotein inhibitior	+	0.7166	71.66%
P-glycoprotein substrate	+	0.6455	64.55%
CYP3A4 substrate	+	0.7113	71.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8741	87.41%
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	+	0.7143	71.43%
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	-	0.9163	91.63%
Skin irritation	-	0.7954	79.54%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7800	78.00%
Micronuclear	+	0.5333	53.33%
Hepatotoxicity	-	0.7907	79.07%
skin sensitisation	-	0.8142	81.42%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7910	79.10%
Acute Oral Toxicity (c)	III	0.5060	50.60%
Estrogen receptor binding	+	0.7711	77.11%
Androgen receptor binding	+	0.5396	53.96%
Thyroid receptor binding	+	0.5551	55.51%
Glucocorticoid receptor binding	+	0.6802	68.02%
Aromatase binding	+	0.5369	53.69%
PPAR gamma	+	0.7318	73.18%
Honey bee toxicity	-	0.6677	66.77%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
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	99.08%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.59%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.28%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.51%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.88%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.83%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.43%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.12%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.55%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.17%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	86.52%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.93%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.64%	86.92%
CHEMBL2581	P07339	Cathepsin D	85.33%	98.95%
CHEMBL4208	P20618	Proteasome component C5	84.39%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.78%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.77%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.94%	95.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.24%	96.21%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	80.14%	98.00%

Plants that contains it

• Buddleja japonica

Cross-Links

• PubChem: 163186338
• LOTUS: LTS0000521
• wikiData: Q104980901