7-Hydroxy-3-[4-hydroxy-2-methoxy-5-(3-methylbut-2-enyl)phenyl]-2,3-dihydrochromen-4-one

Details

• Internal ID: 5610e2b9-6d06-48d7-becb-96813a89f571
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 3-prenylated isoflavanones
• IUPAC Name: 7-hydroxy-3-[4-hydroxy-2-methoxy-5-(3-methylbut-2-enyl)phenyl]-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=CC(=C(C=C1O)OC)C2COC3=C(C2=O)C=CC(=C3)O)C
• SMILES (Isomeric): CC(=CCC1=CC(=C(C=C1O)OC)C2COC3=C(C2=O)C=CC(=C3)O)C
• InChI: InChI=1S/C21H22O5/c1-12(2)4-5-13-8-16(19(25-3)10-18(13)23)17-11-26-20-9-14(22)6-7-15(20)21(17)24/h4,6-10,17,22-23H,5,11H2,1-3H3
• InChI Key: FRFHHICFNPNJOV-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₅
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.14672380 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.97
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9939	99.39%
Caco-2	+	0.8035	80.35%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8651	86.51%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.9037	90.37%
OATP1B3 inhibitior	+	0.8177	81.77%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8233	82.33%
P-glycoprotein inhibitior	+	0.5916	59.16%
P-glycoprotein substrate	-	0.5569	55.69%
CYP3A4 substrate	+	0.5955	59.55%
CYP2C9 substrate	-	0.7880	78.80%
CYP2D6 substrate	-	0.7350	73.50%
CYP3A4 inhibition	-	0.8092	80.92%
CYP2C9 inhibition	+	0.8655	86.55%
CYP2C19 inhibition	+	0.9542	95.42%
CYP2D6 inhibition	-	0.6765	67.65%
CYP1A2 inhibition	+	0.9290	92.90%
CYP2C8 inhibition	+	0.4508	45.08%
CYP inhibitory promiscuity	+	0.9067	90.67%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9513	95.13%
Carcinogenicity (trinary)	Non-required	0.7653	76.53%
Eye corrosion	-	0.9889	98.89%
Eye irritation	+	0.5669	56.69%
Skin irritation	-	0.8158	81.58%
Skin corrosion	-	0.9652	96.52%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5760	57.60%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8425	84.25%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.4945	49.45%
Acute Oral Toxicity (c)	III	0.7271	72.71%
Estrogen receptor binding	+	0.8984	89.84%
Androgen receptor binding	+	0.7622	76.22%
Thyroid receptor binding	+	0.7060	70.60%
Glucocorticoid receptor binding	+	0.8551	85.51%
Aromatase binding	+	0.6449	64.49%
PPAR gamma	+	0.7179	71.79%
Honey bee toxicity	-	0.7822	78.22%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9909	99.09%

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	99.60%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.95%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.37%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.37%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.73%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.21%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.92%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.67%	100.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.64%	89.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.53%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.15%	95.89%
CHEMBL2535	P11166	Glucose transporter	87.75%	98.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.35%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.18%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.24%	92.62%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.09%	89.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.49%	94.45%
CHEMBL3194	P02766	Transthyretin	83.93%	90.71%
CHEMBL4208	P20618	Proteasome component C5	82.64%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.09%	91.19%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.76%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.15%	90.71%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.08%	97.28%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	80.64%	82.67%

Plants that contains it

• Ephedra frustillata
• Erythrina sigmoidea
• Sinningia cardinalis

Cross-Links

• PubChem: 101667574
• LOTUS: LTS0276318
• wikiData: Q105105368