[(2R,3R,4S,5R,6S)-6-[[(4R,4aR)-4a-hydroxy-4-(oxiran-2-yl)-8-oxo-3,4,5,6-tetrahydropyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: d40ecd01-ef4f-4257-9cc8-a124946e6f17
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4S,5R,6S)-6-[[(4R,4aR)-4a-hydroxy-4-(oxiran-2-yl)-8-oxo-3,4,5,6-tetrahydropyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OC2C(OC(C(C2O)O)OC3C(C4(CCOC(=O)C4=CO3)O)C5CO5)CO)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)O[C@H]2[C@H](O[C@H]([C@@H]([C@@H]2O)O)OC3[C@@H]([C@@]4(CCOC(=O)C4=CO3)O)C5CO5)CO)O
• InChI: InChI=1S/C26H30O14/c1-34-15-8-12(2-4-14(15)28)3-5-18(29)39-22-16(9-27)38-25(21(31)20(22)30)40-24-19(17-11-36-17)26(33)6-7-35-23(32)13(26)10-37-24/h2-5,8,10,16-17,19-22,24-25,27-28,30-31,33H,6-7,9,11H2,1H3/b5-3+/t16-,17?,19+,20+,21-,22+,24?,25+,26+/m1/s1
• InChI Key: JORLGXRZMPUTNC-JXBSASMWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀O₁₄
• Molecular Weight: 566.50 g/mol
• Exact Mass: 566.16355563 g/mol
• Topological Polar Surface Area (TPSA): 203.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -1.29
• H-Bond Acceptor: 14
• 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	+	0.8809	88.09%
Caco-2	-	0.8937	89.37%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8153	81.53%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8398	83.98%
OATP1B3 inhibitior	+	0.9402	94.02%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8569	85.69%
BSEP inhibitior	-	0.6281	62.81%
P-glycoprotein inhibitior	-	0.4719	47.19%
P-glycoprotein substrate	+	0.5347	53.47%
CYP3A4 substrate	+	0.7062	70.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8645	86.45%
CYP3A4 inhibition	-	0.8989	89.89%
CYP2C9 inhibition	-	0.7446	74.46%
CYP2C19 inhibition	-	0.7066	70.66%
CYP2D6 inhibition	-	0.8671	86.71%
CYP1A2 inhibition	-	0.7080	70.80%
CYP2C8 inhibition	+	0.7161	71.61%
CYP inhibitory promiscuity	-	0.9134	91.34%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5602	56.02%
Eye corrosion	-	0.9852	98.52%
Eye irritation	-	0.9241	92.41%
Skin irritation	-	0.7666	76.66%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5088	50.88%
Micronuclear	-	0.5826	58.26%
Hepatotoxicity	-	0.5816	58.16%
skin sensitisation	-	0.8223	82.23%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9027	90.27%
Acute Oral Toxicity (c)	III	0.3932	39.32%
Estrogen receptor binding	+	0.8004	80.04%
Androgen receptor binding	+	0.7055	70.55%
Thyroid receptor binding	-	0.5326	53.26%
Glucocorticoid receptor binding	+	0.6712	67.12%
Aromatase binding	+	0.6511	65.11%
PPAR gamma	+	0.6738	67.38%
Honey bee toxicity	-	0.7101	71.01%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8453	84.53%

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	99.74%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.92%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.37%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.36%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.86%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.08%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.09%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.68%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.34%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.44%	92.62%
CHEMBL4208	P20618	Proteasome component C5	89.51%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	85.17%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.36%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.99%	92.94%
CHEMBL2581	P07339	Cathepsin D	83.29%	98.95%
CHEMBL5028	O14672	ADAM10	82.50%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.34%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.18%	95.89%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.36%	97.33%

Plants that contains it

• Swertia angustifolia

Cross-Links

• PubChem: 11968683
• NPASS: NPC296888