3-[2,3-Dihydroxy-4-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-7-hydroxychromen-4-one

Details

• Internal ID: f99ec9cb-e3a8-401c-b4c9-5304a0881331
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > O-methylated isoflavonoids > 4-O-methylated isoflavonoids > 3-hydroxy,4-methoxyisoflavonoids
• IUPAC Name: 3-[2,3-dihydroxy-4-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-7-hydroxychromen-4-one
• SMILES (Canonical): CC(C)(C=C)C1=C(C(=C(C(=C1)C2=COC3=C(C2=O)C=CC(=C3)O)O)O)OC
• SMILES (Isomeric): CC(C)(C=C)C1=C(C(=C(C(=C1)C2=COC3=C(C2=O)C=CC(=C3)O)O)O)OC
• InChI: InChI=1S/C21H20O6/c1-5-21(2,3)15-9-13(18(24)19(25)20(15)26-4)14-10-27-16-8-11(22)6-7-12(16)17(14)23/h5-10,22,24-25H,1H2,2-4H3
• InChI Key: BRLIWKSZZVRVRJ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₆
• Molecular Weight: 368.40 g/mol
• Exact Mass: 368.12598835 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 4.05
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9697	96.97%
Caco-2	-	0.5646	56.46%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7563	75.63%
OATP2B1 inhibitior	-	0.5635	56.35%
OATP1B1 inhibitior	+	0.8754	87.54%
OATP1B3 inhibitior	+	0.9687	96.87%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.4826	48.26%
P-glycoprotein substrate	-	0.7388	73.88%
CYP3A4 substrate	+	0.6485	64.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8153	81.53%
CYP3A4 inhibition	+	0.7078	70.78%
CYP2C9 inhibition	-	0.6700	67.00%
CYP2C19 inhibition	+	0.7226	72.26%
CYP2D6 inhibition	-	0.8596	85.96%
CYP1A2 inhibition	-	0.5133	51.33%
CYP2C8 inhibition	+	0.7309	73.09%
CYP inhibitory promiscuity	+	0.5556	55.56%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5485	54.85%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.5634	56.34%
Skin irritation	-	0.7685	76.85%
Skin corrosion	-	0.9224	92.24%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6380	63.80%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8469	84.69%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6574	65.74%
Acute Oral Toxicity (c)	III	0.5366	53.66%
Estrogen receptor binding	+	0.8433	84.33%
Androgen receptor binding	+	0.8239	82.39%
Thyroid receptor binding	+	0.7291	72.91%
Glucocorticoid receptor binding	+	0.7871	78.71%
Aromatase binding	+	0.6977	69.77%
PPAR gamma	+	0.6688	66.88%
Honey bee toxicity	-	0.8334	83.34%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9879	98.79%

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	99.64%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.81%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.69%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.42%	86.33%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	92.40%	80.78%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.35%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	89.96%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.69%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.20%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.56%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.53%	99.23%
CHEMBL242	Q92731	Estrogen receptor beta	80.67%	98.35%

Plants that contains it

• Dermatophyllum arizonicum
• Dermatophyllum secundiflorum

Cross-Links

• PubChem: 163001673
• LOTUS: LTS0227985
• wikiData: Q104944890