methyl (1S,4aS,6S,7aR)-6-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 9d01b597-17c5-4289-a0b1-ab3e86b91b7d
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: methyl (1S,4aS,6S,7aR)-6-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1CC(C2)COC(=O)C=CC3=CC=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@H]2[C@@H]1C[C@@H](C2)COC(=O)/C=C\C3=CC=C(C=C3)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C26H32O12/c1-34-24(33)18-12-36-25(38-26-23(32)22(31)21(30)19(10-27)37-26)17-9-14(8-16(17)18)11-35-20(29)7-4-13-2-5-15(28)6-3-13/h2-7,12,14,16-17,19,21-23,25-28,30-32H,8-11H2,1H3/b7-4-/t14-,16-,17+,19+,21+,22-,23+,25-,26-/m0/s1
• InChI Key: VMJDMSMQKSZRIP-SWDJDWJUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₂
• Molecular Weight: 536.50 g/mol
• Exact Mass: 536.18937645 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -0.18
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6102	61.02%
Caco-2	-	0.8832	88.32%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.9286	92.86%
Subcellular localzation	Mitochondria	0.6599	65.99%
OATP2B1 inhibitior	-	0.8606	86.06%
OATP1B1 inhibitior	+	0.7782	77.82%
OATP1B3 inhibitior	+	0.9750	97.50%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.5970	59.70%
P-glycoprotein inhibitior	-	0.5664	56.64%
P-glycoprotein substrate	-	0.6218	62.18%
CYP3A4 substrate	+	0.6843	68.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8645	86.45%
CYP3A4 inhibition	-	0.8921	89.21%
CYP2C9 inhibition	-	0.8585	85.85%
CYP2C19 inhibition	-	0.7270	72.70%
CYP2D6 inhibition	-	0.8966	89.66%
CYP1A2 inhibition	-	0.8635	86.35%
CYP2C8 inhibition	+	0.8085	80.85%
CYP inhibitory promiscuity	-	0.6936	69.36%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5644	56.44%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9428	94.28%
Skin irritation	-	0.7957	79.57%
Skin corrosion	-	0.9477	94.77%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7007	70.07%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8412	84.12%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.4619	46.19%
Acute Oral Toxicity (c)	III	0.5646	56.46%
Estrogen receptor binding	+	0.8309	83.09%
Androgen receptor binding	+	0.7171	71.71%
Thyroid receptor binding	-	0.5142	51.42%
Glucocorticoid receptor binding	+	0.5625	56.25%
Aromatase binding	+	0.5227	52.27%
PPAR gamma	+	0.7191	71.91%
Honey bee toxicity	-	0.7501	75.01%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.8866	88.66%

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	98.59%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.54%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.77%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.03%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.22%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.40%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.04%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	87.61%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	87.36%	94.73%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.60%	89.62%
CHEMBL4208	P20618	Proteasome component C5	84.63%	90.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.02%	95.83%
CHEMBL1951	P21397	Monoamine oxidase A	83.16%	91.49%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.08%	89.67%
CHEMBL340	P08684	Cytochrome P450 3A4	81.61%	91.19%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.33%	86.92%

Plants that contains it

• Viburnum luzonicum

Cross-Links

• PubChem: 154496946
• LOTUS: LTS0220646
• wikiData: Q105289004