4H-1-Benzopyran-4-one, 8-[(1S,5R,6S)-6-[2,4-dihydroxy-3-(3-methyl-2-butenyl)benzoyl]-5-(2,4-dihydroxyphenyl)-3-methyl-2-cyclohexen-1-yl]-2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3-methyl-2-butenyl)-

Details

• Internal ID: d020766c-6fe1-4d5d-95a1-3d825256bdbe
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > 8-prenylated flavones
• IUPAC Name: 8-[(1S,5R,6S)-6-[2,4-dihydroxy-3-(3-methylbut-2-enyl)benzoyl]-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-5,7-dihydroxy-2-[2-hydroxy-4-(3-methylbut-2-enoxy)phenyl]-3-(3-methylbut-2-enyl)chromen-4-one
• SMILES (Canonical): CC1=CC(C(C(C1)C2=C(C=C(C=C2)O)O)C(=O)C3=C(C(=C(C=C3)O)CC=C(C)C)O)C4=C(C=C(C5=C4OC(=C(C5=O)CC=C(C)C)C6=C(C=C(C=C6)OCC=C(C)C)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(C(=C(C=C3)O)CC=C(C)C)O)C4=C(C=C(C5=C4OC(=C(C5=O)CC=C(C)C)C6=C(C=C(C=C6)OCC=C(C)C)O)O)O
• InChI: InChI=1S/C50H52O11/c1-25(2)8-12-32-38(52)17-16-34(46(32)57)47(58)43-36(31-14-10-29(51)22-39(31)53)20-28(7)21-37(43)44-41(55)24-42(56)45-48(59)35(13-9-26(3)4)49(61-50(44)45)33-15-11-30(23-40(33)54)60-19-18-27(5)6/h8-11,14-18,21-24,36-37,43,51-57H,12-13,19-20H2,1-7H3/t36-,37-,43-/m0/s1
• InChI Key: ABNFRSPAJQWBFS-QJODFBJXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₅₂O₁₁
• Molecular Weight: 828.90 g/mol
• Exact Mass: 828.35096247 g/mol
• Topological Polar Surface Area (TPSA): 194.00 Ų
• XlogP: 11.10
• Atomic LogP (AlogP): 10.48
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 12

Synonyms

• 8-[(1S,5R,6S)-6-[2,4-dihydroxy-3-(3-methylbut-2-enyl)benzoyl]-5-(2,4-dihydroxyphenyl)-3-methyl-cyclohex-2-en-1-yl]-5,7-dihydroxy-2-[2-hydroxy-4-(3-methylbut-2-enoxy)phenyl]-3-(3-methylbut-2-enyl)chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9754	97.54%
Caco-2	-	0.8613	86.13%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7831	78.31%
OATP2B1 inhibitior	+	0.5735	57.35%
OATP1B1 inhibitior	+	0.8195	81.95%
OATP1B3 inhibitior	+	0.8876	88.76%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9588	95.88%
P-glycoprotein inhibitior	+	0.7982	79.82%
P-glycoprotein substrate	+	0.7628	76.28%
CYP3A4 substrate	+	0.7301	73.01%
CYP2C9 substrate	-	0.5375	53.75%
CYP2D6 substrate	-	0.8195	81.95%
CYP3A4 inhibition	-	0.7164	71.64%
CYP2C9 inhibition	+	0.8373	83.73%
CYP2C19 inhibition	+	0.8328	83.28%
CYP2D6 inhibition	-	0.6867	68.67%
CYP1A2 inhibition	+	0.9113	91.13%
CYP2C8 inhibition	+	0.8361	83.61%
CYP inhibitory promiscuity	+	0.8706	87.06%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7422	74.22%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9023	90.23%
Skin irritation	-	0.8048	80.48%
Skin corrosion	-	0.9442	94.42%
Ames mutagenesis	-	0.5074	50.74%
Human Ether-a-go-go-Related Gene inhibition	+	0.7682	76.82%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8347	83.47%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8747	87.47%
Acute Oral Toxicity (c)	III	0.5511	55.11%
Estrogen receptor binding	+	0.8242	82.42%
Androgen receptor binding	+	0.8247	82.47%
Thyroid receptor binding	+	0.5840	58.40%
Glucocorticoid receptor binding	+	0.7575	75.75%
Aromatase binding	+	0.5883	58.83%
PPAR gamma	+	0.7460	74.60%
Honey bee toxicity	-	0.6917	69.17%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	99.89%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	99.12%	95.17%
CHEMBL2581	P07339	Cathepsin D	98.98%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	97.02%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	96.06%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.51%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.22%	95.56%
CHEMBL4208	P20618	Proteasome component C5	94.39%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.12%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.97%	94.00%
CHEMBL240	Q12809	HERG	91.70%	89.76%
CHEMBL3401	O75469	Pregnane X receptor	91.70%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.06%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.73%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.42%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.97%	96.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.54%	99.23%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	88.77%	94.42%
CHEMBL2535	P11166	Glucose transporter	88.52%	98.75%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.42%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.73%	95.89%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	84.30%	96.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	84.07%	97.53%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	83.91%	89.05%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.64%	91.07%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.09%	85.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.72%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.54%	100.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.53%	96.12%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.46%	92.94%

Plants that contains it

• Morus alba
• Morus mongolica

Cross-Links

• PubChem: 5481220
• NPASS: NPC69200