(-)-5-Hydroxy-2-(hydroxymethyl)-7-(4-hydroxyphenyl)-2-methyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one

Details

• Internal ID: 66262e9c-5f89-486b-bb80-f769a0119e7a
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 6-prenylated isoflavanones
• IUPAC Name: 5-hydroxy-2-(hydroxymethyl)-7-(4-hydroxyphenyl)-2-methylpyrano[3,2-g]chromen-6-one
• InChI: InChI=1S/C20H16O6/c1-20(10-21)7-6-13-15(26-20)8-16-17(18(13)23)19(24)14(9-25-16)11-2-4-12(22)5-3-11/h2-9,21-23H,10H2,1H3
• InChI Key: OVLQTBOVUNAVGU-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₆O₆
• Molecular Weight: 352.30 g/mol
• Exact Mass: 352.09468823 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.03
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• RefChem:203738
• (-)-5-Hydroxy-2-(hydroxymethyl)-7-(4-hydroxyphenyl)-2-methyl-2H,6H-benzo(1,2-b:5,4-b')dipyran-6-one
• (-)-5-Hydroxy-2-(hydroxymethyl)-7-(4-hydroxyphenyl)-2-methyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one
• Erysubin B
• 5-hydroxy-2-(hydroxymethyl)-7-(4-hydroxyphenyl)-2-methylpyrano[3,2-g]chromen-6-one
• orb1682633
• DTXSID101114188
• HY-N3854
• WIA15019
• AKOS032961656
• FS-9586
• DA-73191
• CS-0024341
• (-)-5-Hydroxy-2-(hydroxymethyl)-7-(4-hydroxyphenyl)-2-methyl-2H,6H-benzo[1,2-b:5,4-ba(2)]dipyran-6-one
• 5-Hydroxy-2-(hydroxymethyl)-7-(4-hydroxyphenyl)-2-methyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one
• 5-Hydroxy-2-(hydroxymethyl)-7-(4-hydroxyphenyl)-2-methyl-2H,6H-pyrano[3,2-g]chromen-6-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9765	97.65%
Caco-2	-	0.5841	58.41%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7730	77.30%
OATP2B1 inhibitior	+	0.5642	56.42%
OATP1B1 inhibitior	+	0.8941	89.41%
OATP1B3 inhibitior	+	0.9382	93.82%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8393	83.93%
P-glycoprotein inhibitior	-	0.5473	54.73%
P-glycoprotein substrate	-	0.7280	72.80%
CYP3A4 substrate	+	0.6311	63.11%
CYP2C9 substrate	-	0.6146	61.46%
CYP2D6 substrate	-	0.8377	83.77%
CYP3A4 inhibition	-	0.7182	71.82%
CYP2C9 inhibition	-	0.5400	54.00%
CYP2C19 inhibition	-	0.6030	60.30%
CYP2D6 inhibition	-	0.9196	91.96%
CYP1A2 inhibition	-	0.6647	66.47%
CYP2C8 inhibition	+	0.7487	74.87%
CYP inhibitory promiscuity	+	0.5710	57.10%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5853	58.53%
Eye corrosion	-	0.9906	99.06%
Eye irritation	+	0.5581	55.81%
Skin irritation	-	0.7782	77.82%
Skin corrosion	-	0.9496	94.96%
Ames mutagenesis	-	0.5337	53.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5896	58.96%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	+	0.5304	53.04%
skin sensitisation	-	0.7954	79.54%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6227	62.27%
Acute Oral Toxicity (c)	III	0.5014	50.14%
Estrogen receptor binding	+	0.9156	91.56%
Androgen receptor binding	+	0.8797	87.97%
Thyroid receptor binding	+	0.7219	72.19%
Glucocorticoid receptor binding	+	0.8738	87.38%
Aromatase binding	+	0.8168	81.68%
PPAR gamma	+	0.8547	85.47%
Honey bee toxicity	-	0.8554	85.54%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9116	91.16%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.55%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.49%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.77%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.51%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.26%	85.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.06%	90.71%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	89.74%	91.71%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	89.43%	85.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.95%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.93%	94.00%
CHEMBL242	Q92731	Estrogen receptor beta	87.79%	98.35%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.93%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.94%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.44%	95.56%
CHEMBL1907	P15144	Aminopeptidase N	83.35%	93.31%
CHEMBL1937	Q92769	Histone deacetylase 2	81.76%	94.75%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	81.65%	83.10%
CHEMBL3401	O75469	Pregnane X receptor	81.40%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.76%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.54%	86.92%

Plants that contains it

• Erythrina suberosa
• Genista ephedroides

Cross-Links

• PubChem: 10760434
• LOTUS: LTS0114141
• wikiData: Q105200800