Wighteone

Details

• Internal ID: dfd0bf86-b362-4e73-bdea-3aa84ad5b190
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 6-prenylated isoflavanones
• IUPAC Name: 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)chromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C2=C(C=C1O)OC=C(C2=O)C3=CC=C(C=C3)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C2=C(C=C1O)OC=C(C2=O)C3=CC=C(C=C3)O)O)C
• InChI: InChI=1S/C20H18O5/c1-11(2)3-8-14-16(22)9-17-18(19(14)23)20(24)15(10-25-17)12-4-6-13(21)7-5-12/h3-7,9-10,21-23H,8H2,1-2H3
• InChI Key: KIMDVVKVNNSHGZ-UHFFFAOYSA-N
• Popularity: 32 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₅
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.11542367 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.09
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 51225-30-0
• Erythrinin B
• 5,7-Dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)chromen-4-one
• 5,7,4'-Trihydroxy-6-prenylisoflavone
• CHEBI:10038
• UNII-48ZS74CB9A
• 48ZS74CB9A
• 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-
• CHEMBL393222
• SCHEMBL1170652
• Isoflavone base + 3O, 1Prenyl
• DTXSID30199239
• GLXC-17899
• BDBM50114967
• LMPK12050188
• AKOS015896247
• 5,7,4'-trihydroxy-6-prenyl-isoflavone
• FT-0658111
• A828494
• Q3568003
• B0005-143305
• 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
• 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
• 4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-3-(4-HYDROXYPHENYL)-6-(3-METHYL-2-BUTEN-1-YL)-
• 5,7-DIHYDROXY-3-(4-HYDROXYPHENYL)-6-(3-METHYL-2-BUTEN-1-YL)-4H-1-BENZOPYRAN-4-ONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9914	99.14%
Caco-2	+	0.7452	74.52%
Blood Brain Barrier	-	0.5379	53.79%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7620	76.20%
OATP2B1 inhibitior	+	0.5721	57.21%
OATP1B1 inhibitior	+	0.9386	93.86%
OATP1B3 inhibitior	+	0.9194	91.94%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7168	71.68%
P-glycoprotein inhibitior	-	0.5454	54.54%
P-glycoprotein substrate	-	0.8523	85.23%
CYP3A4 substrate	+	0.5475	54.75%
CYP2C9 substrate	-	0.5755	57.55%
CYP2D6 substrate	-	0.8328	83.28%
CYP3A4 inhibition	+	0.5630	56.30%
CYP2C9 inhibition	+	0.9394	93.94%
CYP2C19 inhibition	+	0.9320	93.20%
CYP2D6 inhibition	-	0.7264	72.64%
CYP1A2 inhibition	+	0.9115	91.15%
CYP2C8 inhibition	+	0.6295	62.95%
CYP inhibitory promiscuity	+	0.9498	94.98%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7012	70.12%
Eye corrosion	-	0.9902	99.02%
Eye irritation	+	0.7013	70.13%
Skin irritation	-	0.7159	71.59%
Skin corrosion	-	0.9161	91.61%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6124	61.24%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.5429	54.29%
skin sensitisation	-	0.7133	71.33%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.5931	59.31%
Acute Oral Toxicity (c)	III	0.6307	63.07%
Estrogen receptor binding	+	0.9372	93.72%
Androgen receptor binding	+	0.8787	87.87%
Thyroid receptor binding	+	0.6223	62.23%
Glucocorticoid receptor binding	+	0.8474	84.74%
Aromatase binding	+	0.7529	75.29%
PPAR gamma	+	0.9369	93.69%
Honey bee toxicity	-	0.8508	85.08%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9944	99.44%

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	98.78%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.58%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.31%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.32%	86.33%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	91.28%	91.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	88.88%	95.64%
CHEMBL3401	O75469	Pregnane X receptor	88.47%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.37%	94.00%
CHEMBL3038469	P24941	CDK2/Cyclin A	86.55%	91.38%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.40%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.09%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.89%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.58%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.14%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.06%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.74%	99.17%
CHEMBL1937	Q92769	Histone deacetylase 2	84.17%	94.75%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.37%	93.10%
CHEMBL3194	P02766	Transthyretin	82.31%	90.71%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.25%	97.28%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.88%	83.10%

Plants that contains it

• Amaranthus spinosus
• Anthyllis hermanniae
• Bolusanthus speciosus
• Calotropis procera
• Centella asiatica
• Erycibe expansa
• Erythrina fusca
• Erythrina latissima
• Erythrina mildbraedii
• Erythrina poeppigiana
• Erythrina suberosa
• Erythrina variegata
• Ficus glumosa
• Ficus mucuso
• Flemingia macrophylla
• Genista ephedroides
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Laburnum anagyroidis
• Lupinus albus
• Lupinus angustifolius
• Lupinus arboreus
• Lupinus luteus
• Maclura cochinchinensis
• Maclura pomifera
• Maclura tricuspidata
• Piper dilatatum
• Sophora flavescens
• Sophora leachiana
• Sophora tomentosa

Cross-Links

• PubChem: 5281814
• NPASS: NPC259166
• ChEMBL: CHEMBL393222
• LOTUS: LTS0136408
• wikiData: Q3568003