[(3S,4aS,5R,6S)-5-ethenyl-1-oxo-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: 6caa1c0e-d28a-4c79-af8c-19a88d811073
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(3S,4aS,5R,6S)-5-ethenyl-1-oxo-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C=CC1C2CC(OC(=O)C2=COC1OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C=CC4=CC(=C(C=C4)O)O
• SMILES (Isomeric): C=C[C@@H]1[C@@H]2C[C@H](OC(=O)C2=CO[C@H]1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC(=O)/C=C/C4=CC(=C(C=C4)O)O
• InChI: InChI=1S/C25H28O13/c1-2-12-13-8-19(36-18(29)6-4-11-3-5-15(27)16(28)7-11)37-23(33)14(13)10-34-24(12)38-25-22(32)21(31)20(30)17(9-26)35-25/h2-7,10,12-13,17,19-22,24-28,30-32H,1,8-9H2/b6-4+/t12-,13+,17-,19+,20-,21+,22-,24+,25+/m1/s1
• InChI Key: JZAJSJKWOPTXFR-VKXHYJBJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₁₃
• Molecular Weight: 536.50 g/mol
• Exact Mass: 536.15299094 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.60
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6449	64.49%
Caco-2	-	0.9054	90.54%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.5747	57.47%
OATP2B1 inhibitior	-	0.8484	84.84%
OATP1B1 inhibitior	+	0.8552	85.52%
OATP1B3 inhibitior	+	0.9584	95.84%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6705	67.05%
P-glycoprotein inhibitior	-	0.5611	56.11%
P-glycoprotein substrate	-	0.7017	70.17%
CYP3A4 substrate	+	0.6532	65.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8670	86.70%
CYP3A4 inhibition	-	0.8040	80.40%
CYP2C9 inhibition	-	0.7155	71.55%
CYP2C19 inhibition	-	0.7216	72.16%
CYP2D6 inhibition	-	0.8757	87.57%
CYP1A2 inhibition	-	0.8436	84.36%
CYP2C8 inhibition	+	0.6736	67.36%
CYP inhibitory promiscuity	-	0.7716	77.16%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7272	72.72%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9119	91.19%
Skin irritation	-	0.7629	76.29%
Skin corrosion	-	0.9437	94.37%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4790	47.90%
Micronuclear	+	0.5433	54.33%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.7617	76.17%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.9098	90.98%
Acute Oral Toxicity (c)	III	0.4141	41.41%
Estrogen receptor binding	+	0.7959	79.59%
Androgen receptor binding	+	0.6468	64.68%
Thyroid receptor binding	+	0.5747	57.47%
Glucocorticoid receptor binding	+	0.5603	56.03%
Aromatase binding	-	0.5134	51.34%
PPAR gamma	+	0.7462	74.62%
Honey bee toxicity	-	0.7130	71.30%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9542	95.42%

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	99.56%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.88%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.21%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	97.12%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.72%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.41%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.19%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.75%	96.00%
CHEMBL226	P30542	Adenosine A1 receptor	86.71%	95.93%
CHEMBL4208	P20618	Proteasome component C5	86.57%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	85.66%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.36%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.11%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.68%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.31%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.10%	95.83%

Plants that contains it

• Bhesa paniculata

Cross-Links

• PubChem: 10052892
• LOTUS: LTS0033283
• wikiData: Q105137320