4-Hydroxy-6-(4-hydroxyphenyl)-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-enyl)-2,3-dihydrofuro[3,2-g]chromen-5-one

Details

• Internal ID: f11c0bd9-2661-4684-9668-11bf207c45fc
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 6-prenylated isoflavanones
• IUPAC Name: 4-hydroxy-6-(4-hydroxyphenyl)-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-enyl)-2,3-dihydrofuro[3,2-g]chromen-5-one
• SMILES (Canonical): CC(=CCC1=C2C(=C(C3=C1OC=C(C3=O)C4=CC=C(C=C4)O)O)CC(O2)C(C)(C)O)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C3=C1OC=C(C3=O)C4=CC=C(C=C4)O)O)CC(O2)C(C)(C)O)C
• InChI: InChI=1S/C25H26O6/c1-13(2)5-10-16-23-17(11-19(31-23)25(3,4)29)21(27)20-22(28)18(12-30-24(16)20)14-6-8-15(26)9-7-14/h5-9,12,19,26-27,29H,10-11H2,1-4H3
• InChI Key: LKFQSODZCVNSSG-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₆O₆
• Molecular Weight: 422.50 g/mol
• Exact Mass: 422.17293854 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.45
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 130289-28-0
• CHEMBL2159049
• 139051-61-9
• Echrenone B10
• Euchrenone b(10)
• SCHEMBL571169
• DTXSID10926666
• BDBM50394205
• LMPK12050185
• 4-Hydroxy-6-(4-hydroxyphenyl)-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-en-1-yl)-2,3-dihydro-5H-furo[3,2-g][1]benzopyran-5-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9957	99.57%
Caco-2	-	0.5879	58.79%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8403	84.03%
OATP2B1 inhibitior	-	0.7094	70.94%
OATP1B1 inhibitior	+	0.8621	86.21%
OATP1B3 inhibitior	+	0.8891	88.91%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8358	83.58%
P-glycoprotein inhibitior	+	0.7063	70.63%
P-glycoprotein substrate	-	0.6178	61.78%
CYP3A4 substrate	+	0.6445	64.45%
CYP2C9 substrate	-	0.5948	59.48%
CYP2D6 substrate	-	0.8240	82.40%
CYP3A4 inhibition	-	0.8197	81.97%
CYP2C9 inhibition	+	0.7713	77.13%
CYP2C19 inhibition	+	0.7872	78.72%
CYP2D6 inhibition	-	0.8759	87.59%
CYP1A2 inhibition	-	0.7321	73.21%
CYP2C8 inhibition	+	0.7192	71.92%
CYP inhibitory promiscuity	+	0.7462	74.62%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5591	55.91%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.5593	55.93%
Skin irritation	-	0.7426	74.26%
Skin corrosion	-	0.9336	93.36%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4096	40.96%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5804	58.04%
skin sensitisation	-	0.7369	73.69%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7046	70.46%
Acute Oral Toxicity (c)	III	0.4098	40.98%
Estrogen receptor binding	+	0.8798	87.98%
Androgen receptor binding	+	0.8022	80.22%
Thyroid receptor binding	+	0.7073	70.73%
Glucocorticoid receptor binding	+	0.8024	80.24%
Aromatase binding	+	0.6555	65.55%
PPAR gamma	+	0.8836	88.36%
Honey bee toxicity	-	0.7710	77.10%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9933	99.33%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	24200 nM	IC50	PMID: 23022281

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.98%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.85%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	94.17%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.04%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.75%	86.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	89.49%	89.34%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.31%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.01%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.29%	94.45%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.41%	95.78%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	83.85%	90.93%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.47%	91.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.75%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.70%	97.09%
CHEMBL242	Q92731	Estrogen receptor beta	82.27%	98.35%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	81.85%	95.64%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.70%	100.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.19%	86.92%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.12%	85.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.39%	96.90%

Plants that contains it

• Deguelia scandens
• Erythrina addisoniae
• Erythrina costaricensis
• Erythrina senegalensis
• Erythrina suberosa
• Erythrina variegata
• Millettia pachycarpa

Cross-Links

• PubChem: 195652
• NPASS: NPC327269
• ChEMBL: CHEMBL2159049
• LOTUS: LTS0273024
• wikiData: Q82901250