(2S,3R)-3-[4-(5,7-dihydroxy-3-methoxy-4-oxochromen-2-yl)-2-hydroxy-3-(3-methylbut-2-enyl)phenoxy]-2,3,5,7-tetrahydroxy-2-(4-hydroxyphenyl)chromen-4-one

Details

• Internal ID: fd0998d4-8e84-4c0c-8573-c4daad6258e3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > 2-prenylated flavones
• IUPAC Name: (2S,3R)-3-[4-(5,7-dihydroxy-3-methoxy-4-oxochromen-2-yl)-2-hydroxy-3-(3-methylbut-2-enyl)phenoxy]-2,3,5,7-tetrahydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1O)OC2(C(=O)C3=C(C=C(C=C3OC2(C4=CC=C(C=C4)O)O)O)O)O)C5=C(C(=O)C6=C(C=C(C=C6O5)O)O)OC)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1O)O[C@@]2(C(=O)C3=C(C=C(C=C3O[C@]2(C4=CC=C(C=C4)O)O)O)O)O)C5=C(C(=O)C6=C(C=C(C=C6O5)O)O)OC)C
• InChI: InChI=1S/C36H30O14/c1-16(2)4-9-21-22(32-33(47-3)31(43)28-23(40)12-19(38)14-26(28)48-32)10-11-25(30(21)42)49-36(46)34(44)29-24(41)13-20(39)15-27(29)50-35(36,45)17-5-7-18(37)8-6-17/h4-8,10-15,37-42,45-46H,9H2,1-3H3/t35-,36+/m0/s1
• InChI Key: JTYQTVPZTBVCSU-MPQUPPDSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₃₀O₁₄
• Molecular Weight: 686.60 g/mol
• Exact Mass: 686.16355563 g/mol
• Topological Polar Surface Area (TPSA): 233.00 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 4.40
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9001	90.01%
Caco-2	-	0.8621	86.21%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5724	57.24%
OATP2B1 inhibitior	+	0.5683	56.83%
OATP1B1 inhibitior	+	0.7648	76.48%
OATP1B3 inhibitior	+	0.8220	82.20%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9960	99.60%
P-glycoprotein inhibitior	+	0.8067	80.67%
P-glycoprotein substrate	+	0.7186	71.86%
CYP3A4 substrate	+	0.6952	69.52%
CYP2C9 substrate	-	0.6054	60.54%
CYP2D6 substrate	-	0.8310	83.10%
CYP3A4 inhibition	-	0.8521	85.21%
CYP2C9 inhibition	+	0.5224	52.24%
CYP2C19 inhibition	+	0.5679	56.79%
CYP2D6 inhibition	-	0.8821	88.21%
CYP1A2 inhibition	-	0.8807	88.07%
CYP2C8 inhibition	+	0.8687	86.87%
CYP inhibitory promiscuity	-	0.6010	60.10%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5964	59.64%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.8766	87.66%
Skin irritation	-	0.7576	75.76%
Skin corrosion	-	0.9381	93.81%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4030	40.30%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8400	84.00%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.8423	84.23%
Acute Oral Toxicity (c)	III	0.6202	62.02%
Estrogen receptor binding	+	0.8551	85.51%
Androgen receptor binding	+	0.8397	83.97%
Thyroid receptor binding	+	0.5939	59.39%
Glucocorticoid receptor binding	+	0.8142	81.42%
Aromatase binding	+	0.6670	66.70%
PPAR gamma	+	0.7422	74.22%
Honey bee toxicity	-	0.7317	73.17%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9941	99.41%

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	99.68%	91.11%
CHEMBL240	Q12809	HERG	97.80%	89.76%
CHEMBL2581	P07339	Cathepsin D	97.67%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.76%	94.45%
CHEMBL3194	P02766	Transthyretin	95.21%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.88%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.49%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	94.22%	91.49%
CHEMBL4208	P20618	Proteasome component C5	93.66%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.06%	94.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.46%	95.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.95%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.90%	96.95%
CHEMBL1937	Q92769	Histone deacetylase 2	88.13%	94.75%
CHEMBL1929	P47989	Xanthine dehydrogenase	87.15%	96.12%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	86.80%	93.10%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.10%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.70%	99.17%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.59%	94.42%
CHEMBL3401	O75469	Pregnane X receptor	84.56%	94.73%
CHEMBL2535	P11166	Glucose transporter	83.35%	98.75%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	83.26%	82.38%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.39%	96.21%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.16%	95.64%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.01%	89.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.00%	96.90%

Plants that contains it

• Podophyllum versipelle

Cross-Links

• PubChem: 162895237
• LOTUS: LTS0018883
• wikiData: Q105135085