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

Details

• Internal ID: 13b4e56d-3ade-4958-8e57-9360737169d5
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
• IUPAC Name: [(2S,3S,4R,5S,6R)-3,5-diacetyloxy-2-[[(1R,2S,4S,5R,6S,10R)-2-(hydroxymethyl)-10-[(2R,3S,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-4-yl] (E)-3-phenylprop-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=CC=C6)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)OC(=O)/C=C/C6=CC=CC=C6)OC(=O)C
• InChI: InChI=1S/C34H42O17/c1-15-26(45-16(2)37)28(48-21(39)10-9-18-7-5-4-6-8-18)29(46-17(3)38)33(44-15)49-27-19-11-12-43-31(22(19)34(14-36)30(27)51-34)50-32-25(42)24(41)23(40)20(13-35)47-32/h4-12,15,19-20,22-33,35-36,40-42H,13-14H2,1-3H3/b10-9+/t15-,19+,20-,22+,23-,24+,25+,26+,27-,28-,29+,30+,31-,32-,33+,34-/m1/s1
• InChI Key: XTDOKCBBQODVJW-DOQPPTJCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₂O₁₇
• Molecular Weight: 722.70 g/mol
• Exact Mass: 722.24219987 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.33
• H-Bond Acceptor: 17
• H-Bond Donor: 5
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5764	57.64%
Caco-2	-	0.8706	87.06%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6482	64.82%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.7941	79.41%
OATP1B3 inhibitior	+	0.9423	94.23%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7617	76.17%
P-glycoprotein inhibitior	+	0.6930	69.30%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6967	69.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8818	88.18%
CYP3A4 inhibition	-	0.9080	90.80%
CYP2C9 inhibition	-	0.9095	90.95%
CYP2C19 inhibition	-	0.8878	88.78%
CYP2D6 inhibition	-	0.9395	93.95%
CYP1A2 inhibition	-	0.9016	90.16%
CYP2C8 inhibition	+	0.6861	68.61%
CYP inhibitory promiscuity	-	0.8305	83.05%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6132	61.32%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9189	91.89%
Skin irritation	-	0.7854	78.54%
Skin corrosion	-	0.9446	94.46%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7644	76.44%
Micronuclear	-	0.5541	55.41%
Hepatotoxicity	-	0.8157	81.57%
skin sensitisation	-	0.8355	83.55%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6184	61.84%
Acute Oral Toxicity (c)	III	0.4183	41.83%
Estrogen receptor binding	+	0.7718	77.18%
Androgen receptor binding	+	0.5700	57.00%
Thyroid receptor binding	+	0.5489	54.89%
Glucocorticoid receptor binding	+	0.6677	66.77%
Aromatase binding	-	0.5172	51.72%
PPAR gamma	+	0.7387	73.87%
Honey bee toxicity	-	0.6889	68.89%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.7949	79.49%

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	99.18%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.11%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.34%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.01%	96.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	93.73%	94.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.52%	96.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	93.38%	94.08%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.30%	89.00%
CHEMBL2581	P07339	Cathepsin D	93.04%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.81%	85.14%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	91.13%	94.23%
CHEMBL3401	O75469	Pregnane X receptor	91.12%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.03%	97.36%
CHEMBL5028	O14672	ADAM10	83.11%	97.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.68%	95.50%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	82.10%	87.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.12%	99.17%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	80.41%	89.44%

Plants that contains it

• Scrophularia deserti

Cross-Links

• PubChem: 163013636
• LOTUS: LTS0110123
• wikiData: Q105341476