[(1S,6S,7R)-4-[[4,5-dihydroxy-6-(hydroxymethyl)-3-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]oxymethyl]-6,7-bis(ethoxycarbonyloxy)-7-hydroxy-1-methyl-4a,5,6,7a-tetrahydrocyclopenta[c]pyran-1-yl] 3-methylbutanoate

Details

• Internal ID: a419cc36-520c-40b9-be18-5b9e4bbfee2a
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(1S,6S,7R)-4-[[4,5-dihydroxy-6-(hydroxymethyl)-3-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]oxymethyl]-6,7-bis(ethoxycarbonyloxy)-7-hydroxy-1-methyl-4a,5,6,7a-tetrahydrocyclopenta[c]pyran-1-yl] 3-methylbutanoate
• SMILES (Canonical): CCOC(=O)OC1CC2C(C1(O)OC(=O)OCC)C(OC=C2COC3C(C(C(C(O3)CO)O)O)OC(=O)C=CC4=CC=C(C=C4)O)(C)OC(=O)CC(C)C
• SMILES (Isomeric): CCOC(=O)O[C@H]1CC2C([C@@]1(O)OC(=O)OCC)[C@](OC=C2COC3C(C(C(C(O3)CO)O)O)OC(=O)/C=C\C4=CC=C(C=C4)O)(C)OC(=O)CC(C)C
• InChI: InChI=1S/C36H48O18/c1-6-46-33(43)51-25-15-23-21(18-49-35(5,53-27(40)14-19(3)4)31(23)36(25,45)54-34(44)47-7-2)17-48-32-30(29(42)28(41)24(16-37)50-32)52-26(39)13-10-20-8-11-22(38)12-9-20/h8-13,18-19,23-25,28-32,37-38,41-42,45H,6-7,14-17H2,1-5H3/b13-10-/t23?,24?,25-,28?,29?,30?,31?,32?,35-,36-/m0/s1
• InChI Key: TXBXKTCBHQVGDF-AHMVLXFVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₈O₁₈
• Molecular Weight: 768.80 g/mol
• Exact Mass: 768.28406468 g/mol
• Topological Polar Surface Area (TPSA): 253.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.03
• H-Bond Acceptor: 18
• H-Bond Donor: 5
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7819	78.19%
Caco-2	-	0.8673	86.73%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.7580	75.80%
OATP2B1 inhibitior	-	0.8604	86.04%
OATP1B1 inhibitior	+	0.7962	79.62%
OATP1B3 inhibitior	+	0.9115	91.15%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8003	80.03%
P-glycoprotein inhibitior	+	0.7353	73.53%
P-glycoprotein substrate	+	0.6334	63.34%
CYP3A4 substrate	+	0.7213	72.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8673	86.73%
CYP3A4 inhibition	-	0.5475	54.75%
CYP2C9 inhibition	-	0.7214	72.14%
CYP2C19 inhibition	-	0.7058	70.58%
CYP2D6 inhibition	-	0.9046	90.46%
CYP1A2 inhibition	-	0.7614	76.14%
CYP2C8 inhibition	+	0.7921	79.21%
CYP inhibitory promiscuity	-	0.6475	64.75%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5497	54.97%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9137	91.37%
Skin irritation	-	0.7584	75.84%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4573	45.73%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.8357	83.57%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8769	87.69%
Acute Oral Toxicity (c)	III	0.6350	63.50%
Estrogen receptor binding	+	0.7874	78.74%
Androgen receptor binding	+	0.7555	75.55%
Thyroid receptor binding	+	0.5146	51.46%
Glucocorticoid receptor binding	+	0.6996	69.96%
Aromatase binding	+	0.5817	58.17%
PPAR gamma	+	0.7226	72.26%
Honey bee toxicity	-	0.7046	70.46%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9903	99.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	97.79%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.61%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.54%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	96.84%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.76%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	96.67%	95.93%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.30%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.20%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.04%	86.33%
CHEMBL2581	P07339	Cathepsin D	93.43%	98.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	92.98%	97.21%
CHEMBL206	P03372	Estrogen receptor alpha	91.92%	97.64%
CHEMBL2996	Q05655	Protein kinase C delta	91.17%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.06%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.51%	93.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.02%	89.62%
CHEMBL5255	O00206	Toll-like receptor 4	87.66%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.54%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.99%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.73%	96.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.35%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.14%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	85.91%	94.73%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	85.20%	90.93%
CHEMBL242	Q92731	Estrogen receptor beta	84.55%	98.35%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.69%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	82.92%	90.17%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.84%	82.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.78%	91.07%

Plants that contains it

• Viburnum tinus

Cross-Links

• PubChem: 162817623
• LOTUS: LTS0253705
• wikiData: Q105266367