[(2S,3R,4R,5R,6S)-4,5-dihydroxy-2-[[(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2R,3S,4R,5R,6S)-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-phenylprop-2-enoate

Details

• Internal ID: 3ceef6c5-a278-4b67-9b8e-fc5999b23243
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
• IUPAC Name: [(2S,3R,4R,5R,6S)-4,5-dihydroxy-2-[[(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2R,3S,4R,5R,6S)-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-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=CC6=CC=CC=C6)O)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=C/C6=CC=CC=C6)O)O
• InChI: InChI=1S/C30H38O15/c1-13-19(34)22(37)25(42-17(33)8-7-14-5-3-2-4-6-14)29(40-13)43-24-15-9-10-39-27(18(15)30(12-32)26(24)45-30)44-28-23(38)21(36)20(35)16(11-31)41-28/h2-10,13,15-16,18-29,31-32,34-38H,11-12H2,1H3/b8-7+/t13-,15+,16-,18+,19-,20-,21+,22+,23-,24-,25+,26-,27-,28+,29-,30+/m0/s1
• InChI Key: RLGYLKXDNQBDCU-OGLLXYHISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₈O₁₅
• Molecular Weight: 638.60 g/mol
• Exact Mass: 638.22107050 g/mol
• Topological Polar Surface Area (TPSA): 227.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.47
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5181	51.81%
Caco-2	-	0.8853	88.53%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6629	66.29%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.8087	80.87%
OATP1B3 inhibitior	+	0.9595	95.95%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.4698	46.98%
P-glycoprotein inhibitior	-	0.4770	47.70%
P-glycoprotein substrate	-	0.5400	54.00%
CYP3A4 substrate	+	0.6792	67.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8785	87.85%
CYP3A4 inhibition	-	0.9456	94.56%
CYP2C9 inhibition	-	0.9117	91.17%
CYP2C19 inhibition	-	0.8243	82.43%
CYP2D6 inhibition	-	0.9207	92.07%
CYP1A2 inhibition	-	0.8889	88.89%
CYP2C8 inhibition	+	0.6704	67.04%
CYP inhibitory promiscuity	-	0.7606	76.06%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5872	58.72%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9267	92.67%
Skin irritation	-	0.7890	78.90%
Skin corrosion	-	0.9482	94.82%
Ames mutagenesis	-	0.6670	66.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7690	76.90%
Micronuclear	-	0.5841	58.41%
Hepatotoxicity	-	0.8282	82.82%
skin sensitisation	-	0.8180	81.80%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8536	85.36%
Acute Oral Toxicity (c)	III	0.4425	44.25%
Estrogen receptor binding	+	0.7279	72.79%
Androgen receptor binding	+	0.5326	53.26%
Thyroid receptor binding	+	0.5289	52.89%
Glucocorticoid receptor binding	+	0.5967	59.67%
Aromatase binding	-	0.4839	48.39%
PPAR gamma	+	0.6763	67.63%
Honey bee toxicity	-	0.7190	71.90%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.6729	67.29%

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	98.99%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.22%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.47%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.58%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	92.96%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.79%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.73%	89.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	91.45%	94.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.96%	94.62%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	90.68%	94.08%
CHEMBL3401	O75469	Pregnane X receptor	90.14%	94.73%
CHEMBL2581	P07339	Cathepsin D	89.64%	98.95%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.79%	97.36%
CHEMBL1951	P21397	Monoamine oxidase A	83.89%	91.49%
CHEMBL5028	O14672	ADAM10	82.06%	97.50%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.63%	89.67%
CHEMBL4208	P20618	Proteasome component C5	81.13%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.06%	99.17%

Plants that contains it

• Verbascum spinosum

Cross-Links

• PubChem: 10817879
• LOTUS: LTS0232456
• wikiData: Q105240033