(2E)-3-(2,4-Dihydroxyphenyl)-1-[3-[(1S,5S,6R)-5-(2,4-dihydroxyphenyl)-6-[(5-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)carbonyl]-3-methyl-2-cyclohexen-1-yl]-2,4-dihydroxyphenyl]-2-propen-1-one

Details

• Internal ID: 7928f013-5298-4882-8315-3acbe7837dd2
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 2-Hydroxychalcones
• IUPAC Name: (E)-3-(2,4-dihydroxyphenyl)-1-[3-[(1S,5S,6R)-5-(2,4-dihydroxyphenyl)-6-(5-hydroxy-2,2-dimethylchromene-6-carbonyl)-3-methylcyclohex-2-en-1-yl]-2,4-dihydroxyphenyl]prop-2-en-1-one
• SMILES (Canonical): CC1=CC(C(C(C1)C2=C(C=C(C=C2)O)O)C(=O)C3=C(C4=C(C=C3)OC(C=C4)(C)C)O)C5=C(C=CC(=C5O)C(=O)C=CC6=C(C=C(C=C6)O)O)O
• SMILES (Isomeric): CC1=C[C@@H]([C@@H]([C@H](C1)C2=C(C=C(C=C2)O)O)C(=O)C3=C(C4=C(C=C3)OC(C=C4)(C)C)O)C5=C(C=CC(=C5O)C(=O)/C=C/C6=C(C=C(C=C6)O)O)O
• InChI: InChI=1S/C40H36O10/c1-20-16-28(24-8-7-23(42)19-33(24)46)35(39(49)27-10-13-34-26(37(27)47)14-15-40(2,3)50-34)29(17-20)36-31(44)12-9-25(38(36)48)30(43)11-5-21-4-6-22(41)18-32(21)45/h4-15,17-19,28-29,35,41-42,44-48H,16H2,1-3H3/b11-5+/t28-,29+,35-/m1/s1
• InChI Key: JIQSDJNLGMFGDV-LIKPGJMYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₃₆O₁₀
• Molecular Weight: 676.70 g/mol
• Exact Mass: 676.23084734 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: 7.20
• Atomic LogP (AlogP): 7.42
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• (2E)-3-(2,4-Dihydroxyphenyl)-1-[3-[(1S,5S,6R)-5-(2,4-dihydroxyphenyl)-6-[(5-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)carbonyl]-3-methyl-2-cyclohexen-1-yl]-2,4-dihydroxyphenyl]-2-propen-1-one
• (+)-Artonin D
• 8QLU5CVK7G
• DTXSID601098541
• 2-Propen-1-one, 3-(2,4-dihydroxyphenyl)-1-[3-[(1S,5S,6R)-5-(2,4-dihydroxyphenyl)-6-[(5-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)carbonyl]-3-methyl-2-cyclohexen-1-yl]-2,4-dihydroxyphenyl]-, (2E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9729	97.29%
Caco-2	-	0.8725	87.25%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7548	75.48%
OATP2B1 inhibitior	+	0.5747	57.47%
OATP1B1 inhibitior	+	0.8358	83.58%
OATP1B3 inhibitior	+	0.9523	95.23%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9525	95.25%
P-glycoprotein inhibitior	+	0.8020	80.20%
P-glycoprotein substrate	+	0.7487	74.87%
CYP3A4 substrate	+	0.7155	71.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8370	83.70%
CYP3A4 inhibition	-	0.5227	52.27%
CYP2C9 inhibition	+	0.9019	90.19%
CYP2C19 inhibition	+	0.8059	80.59%
CYP2D6 inhibition	-	0.8400	84.00%
CYP1A2 inhibition	+	0.6736	67.36%
CYP2C8 inhibition	+	0.8563	85.63%
CYP inhibitory promiscuity	+	0.8601	86.01%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5413	54.13%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.8964	89.64%
Skin irritation	-	0.7177	71.77%
Skin corrosion	-	0.9253	92.53%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9303	93.03%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.7835	78.35%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7981	79.81%
Acute Oral Toxicity (c)	III	0.4348	43.48%
Estrogen receptor binding	+	0.8344	83.44%
Androgen receptor binding	+	0.8346	83.46%
Thyroid receptor binding	+	0.6222	62.22%
Glucocorticoid receptor binding	+	0.8131	81.31%
Aromatase binding	+	0.5372	53.72%
PPAR gamma	+	0.7393	73.93%
Honey bee toxicity	-	0.7561	75.61%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9961	99.61%

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	99.78%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.29%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.33%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.86%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.09%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.96%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.77%	86.33%
CHEMBL4208	P20618	Proteasome component C5	91.42%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.82%	97.36%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.38%	90.71%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.50%	93.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.61%	99.15%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	85.49%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.07%	99.23%
CHEMBL3194	P02766	Transthyretin	84.84%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.33%	94.45%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	83.48%	89.05%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	83.20%	85.11%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.07%	85.00%
CHEMBL3401	O75469	Pregnane X receptor	82.99%	94.73%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.72%	89.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.46%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.28%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.25%	100.00%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.66%	90.24%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	81.28%	85.49%
CHEMBL2535	P11166	Glucose transporter	80.85%	98.75%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	80.66%	96.69%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.19%	91.71%

Plants that contains it

• Artocarpus integer
• Sorocea bonplandii

Cross-Links

• PubChem: 14681574
• LOTUS: LTS0064301
• wikiData: Q104402882