5,6,7,4'-Tetrahydroxy-8-methoxyisoflavone

Details

• Internal ID: a59b2f9d-5e68-4d47-9370-2e8670bdad3a
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflav-2-enes > Isoflavones
• IUPAC Name: 5,6,7-trihydroxy-3-(4-hydroxyphenyl)-8-methoxychromen-4-one
• SMILES (Canonical): COC1=C2C(=C(C(=C1O)O)O)C(=O)C(=CO2)C3=CC=C(C=C3)O
• SMILES (Isomeric): COC1=C2C(=C(C(=C1O)O)O)C(=O)C(=CO2)C3=CC=C(C=C3)O
• InChI: InChI=1S/C16H12O7/c1-22-16-14(21)13(20)12(19)10-11(18)9(6-23-15(10)16)7-2-4-8(17)5-3-7/h2-6,17,19-21H,1H3
• InChI Key: NHKRWDZHHWTCAH-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₇
• Molecular Weight: 316.26 g/mol
• Exact Mass: 316.05830272 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.29
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• LMPK12050443

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9095	90.95%
Caco-2	+	0.7695	76.95%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6297	62.97%
OATP2B1 inhibitior	-	0.5642	56.42%
OATP1B1 inhibitior	+	0.8834	88.34%
OATP1B3 inhibitior	+	0.9904	99.04%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7669	76.69%
P-glycoprotein inhibitior	-	0.7046	70.46%
P-glycoprotein substrate	-	0.9280	92.80%
CYP3A4 substrate	+	0.5481	54.81%
CYP2C9 substrate	-	0.6887	68.87%
CYP2D6 substrate	-	0.8370	83.70%
CYP3A4 inhibition	+	0.6330	63.30%
CYP2C9 inhibition	-	0.7982	79.82%
CYP2C19 inhibition	-	0.6361	63.61%
CYP2D6 inhibition	-	0.8687	86.87%
CYP1A2 inhibition	+	0.9091	90.91%
CYP2C8 inhibition	+	0.6935	69.35%
CYP inhibitory promiscuity	+	0.7089	70.89%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6208	62.08%
Eye corrosion	-	0.9790	97.90%
Eye irritation	+	0.8853	88.53%
Skin irritation	-	0.6006	60.06%
Skin corrosion	-	0.9153	91.53%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7233	72.33%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.9054	90.54%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5280	52.80%
Acute Oral Toxicity (c)	III	0.6309	63.09%
Estrogen receptor binding	+	0.8516	85.16%
Androgen receptor binding	+	0.8129	81.29%
Thyroid receptor binding	+	0.7213	72.13%
Glucocorticoid receptor binding	+	0.8704	87.04%
Aromatase binding	+	0.6383	63.83%
PPAR gamma	+	0.7848	78.48%
Honey bee toxicity	-	0.8867	88.67%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8562	85.62%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.44%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.86%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.33%	94.00%
CHEMBL242	Q92731	Estrogen receptor beta	88.84%	98.35%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.30%	86.33%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.84%	91.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.69%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.38%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.71%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.58%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.80%	99.15%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.29%	95.64%

Plants that contains it

• Iris domestica
• Iris milesii

Cross-Links

• PubChem: 44257374
• NPASS: NPC56836
• LOTUS: LTS0195398
• wikiData: Q105179447