7,4'-Dimethoxy-5-hydroxyisoflavone

Details

• Internal ID: 3d16795c-4efb-4cc4-8301-44f9ec51bc84
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > O-methylated isoflavonoids > 7-O-methylated isoflavonoids > 7-O-methylisoflavones
• IUPAC Name: 5-hydroxy-7-methoxy-3-(4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)OC
• SMILES (Isomeric): COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)OC
• InChI: InChI=1S/C17H14O5/c1-20-11-5-3-10(4-6-11)13-9-22-15-8-12(21-2)7-14(18)16(15)17(13)19/h3-9,18H,1-2H3
• InChI Key: DQNLRFRBAWCJHQ-UHFFFAOYSA-N
• Popularity: 20 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₅
• Molecular Weight: 298.29 g/mol
• Exact Mass: 298.08412354 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.18
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 7-O-Methylbiochanin A
• 7,4'-Dimethoxy-5-hydroxyisoflavone
• 5-Hydroxy-4',7-dimethoxyisoflavone
• GENISTEIN-4',7-DIMETHYL ETHER
• 5-hydroxy-7-methoxy-3-(4-methoxyphenyl)chromen-4-one
• 5-Hydroxy-7-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one
• 4',7-dimethoxy-5-hydroxyisoflavone
• NSC 604926
• 4H-1-Benzopyran-4-one, 5-hydroxy-7-methoxy-3-(4-methoxyphenyl)-
• NSC604926
• Biochanin A 7-methyl ether
• O617EDC7HT
• MLS000570796
• Genistein-7,4'-dimethyl ether
• NSC-604926
• 7-methoxy-3-(4-methoxyphenyl)-5-oxidanyl-chromen-4-one
• SMR000150588
• 5-hydroxy-7-methoxy-3-(4-methoxyphenyl)-1-benzopyran-4-one
• dimethylgenistein
• genistein 4',7-dimethyl ether
• Spectrum_001916
• SpecPlus_000385
• Spectrum5_001866
• UNII-O617EDC7HT
• Oprea1_378910
• KBioSS_002458
• DivK1c_006481
• SCHEMBL572108
• CHEMBL464433
• BDBM49475
• cid_5386259
• KBio1_001425
• KBio2_002451
• KBio2_005019
• KBio2_007587
• DTXSID60187684
• DQNLRFRBAWCJHQ-UHFFFAOYSA-N
• 5-hydroxy4',7-dimethoxyisoflavone
• 4',7-DI-O-METHYLGENISTEIN
• BCP10000
• HY-N7655
• 5-hydroxy-7,4'-dimethoxyisoflavone
• BIOCHANIN A, 7-METHYL ETHER
• BIOCHANIN A, MONOMETHYL ETHER
• MFCD00075976
• AKOS003624283
• CCG-231517
• NCGC00246143-01
• BS-49344
• NCI60_004625
• CS-0135002
• FT-0639155
• HYDROXY-4',7-DIMETHOXYISOFLAVONE, 5-
• E78703
• ISOFLAVONE, 5-HYDROXY-4',7-DIMETHOXY-
• 5-hydroxy-7-methoxy-3-(4-methoxyphenyl)chromone
• AB00052939-11
• A822068
• Z56823094
• 5-HYDROXY-7-METHOXY-3-(4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9895	98.95%
Caco-2	+	0.9441	94.41%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8105	81.05%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9559	95.59%
OATP1B3 inhibitior	+	0.9934	99.34%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6033	60.33%
P-glycoprotein inhibitior	+	0.7303	73.03%
P-glycoprotein substrate	-	0.9553	95.53%
CYP3A4 substrate	+	0.5357	53.57%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.5759	57.59%
CYP2C9 inhibition	+	0.7301	73.01%
CYP2C19 inhibition	+	0.9119	91.19%
CYP2D6 inhibition	-	0.8489	84.89%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.5516	55.16%
CYP inhibitory promiscuity	+	0.7230	72.30%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9413	94.13%
Carcinogenicity (trinary)	Non-required	0.6131	61.31%
Eye corrosion	-	0.9773	97.73%
Eye irritation	+	0.6249	62.49%
Skin irritation	-	0.6644	66.44%
Skin corrosion	-	0.9843	98.43%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5987	59.87%
Micronuclear	+	0.8959	89.59%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.9635	96.35%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.6444	64.44%
Acute Oral Toxicity (c)	III	0.5335	53.35%
Estrogen receptor binding	+	0.9447	94.47%
Androgen receptor binding	+	0.9382	93.82%
Thyroid receptor binding	+	0.8515	85.15%
Glucocorticoid receptor binding	+	0.8221	82.21%
Aromatase binding	+	0.8645	86.45%
PPAR gamma	+	0.7605	76.05%
Honey bee toxicity	-	0.9316	93.16%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9126	91.26%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3356	P05177	Cytochrome P450 1A2	3162.28 nM	AC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	25118.86 nM	AC50	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	2818.38 nM	AC50	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	35.48 nM	AC50	via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	631 nM; 631 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	1000 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	12589.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.88%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.74%	99.15%
CHEMBL2581	P07339	Cathepsin D	95.26%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.79%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.23%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.55%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.35%	86.33%
CHEMBL1907	P15144	Aminopeptidase N	88.85%	93.31%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.38%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.03%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.94%	99.17%
CHEMBL4208	P20618	Proteasome component C5	87.60%	90.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	86.60%	96.12%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.52%	93.65%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.86%	96.09%

Plants that contains it

• Asclepias vestita
• Heliotropium hirsutissimum
• Inulanthera calva
• Klasea sogdiana
• Myristica malabarica
• Nicotiana raimondii
• Ormosia henryi
• Peperomia blanda
• Scolopia chinensis
• Trollius europaeus

Cross-Links

• PubChem: 5386259
• NPASS: NPC116632
• ChEMBL: CHEMBL464433
• LOTUS: LTS0032344
• wikiData: Q72467968