1-[2,4-Dihydroxy-6-methoxy-3,5-bis(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

Details

• Internal ID: d6c44d1a-8514-4c82-8def-d4cb60e5edc6
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 3-prenylated chalcones
• IUPAC Name: 1-[2,4-dihydroxy-6-methoxy-3,5-bis(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• SMILES (Canonical): CC(=CCC1=C(C(=C(C(=C1O)C(=O)C=CC2=CC=C(C=C2)O)OC)CC=C(C)C)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=C(C(=C1O)C(=O)C=CC2=CC=C(C=C2)O)OC)CC=C(C)C)O)C
• InChI: InChI=1S/C26H30O5/c1-16(2)6-13-20-24(29)21(14-7-17(3)4)26(31-5)23(25(20)30)22(28)15-10-18-8-11-19(27)12-9-18/h6-12,15,27,29-30H,13-14H2,1-5H3
• InChI Key: HOTYOZVURUOVTK-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀O₅
• Molecular Weight: 422.50 g/mol
• Exact Mass: 422.20932405 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 7.00
• Atomic LogP (AlogP): 5.73
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9937	99.37%
Caco-2	+	0.6009	60.09%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8120	81.20%
OATP2B1 inhibitior	-	0.5711	57.11%
OATP1B1 inhibitior	+	0.8275	82.75%
OATP1B3 inhibitior	+	0.8776	87.76%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9087	90.87%
P-glycoprotein inhibitior	+	0.8105	81.05%
P-glycoprotein substrate	-	0.7415	74.15%
CYP3A4 substrate	+	0.5202	52.02%
CYP2C9 substrate	-	0.7875	78.75%
CYP2D6 substrate	-	0.8322	83.22%
CYP3A4 inhibition	-	0.6712	67.12%
CYP2C9 inhibition	+	0.8238	82.38%
CYP2C19 inhibition	+	0.9049	90.49%
CYP2D6 inhibition	-	0.7020	70.20%
CYP1A2 inhibition	+	0.7755	77.55%
CYP2C8 inhibition	+	0.6744	67.44%
CYP inhibitory promiscuity	+	0.8631	86.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7916	79.16%
Carcinogenicity (trinary)	Non-required	0.7686	76.86%
Eye corrosion	-	0.9897	98.97%
Eye irritation	+	0.6159	61.59%
Skin irritation	-	0.8160	81.60%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8111	81.11%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.6343	63.43%
skin sensitisation	-	0.6648	66.48%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.7440	74.40%
Acute Oral Toxicity (c)	III	0.6824	68.24%
Estrogen receptor binding	+	0.9328	93.28%
Androgen receptor binding	+	0.8002	80.02%
Thyroid receptor binding	+	0.6695	66.95%
Glucocorticoid receptor binding	+	0.8768	87.68%
Aromatase binding	+	0.7488	74.88%
PPAR gamma	+	0.9034	90.34%
Honey bee toxicity	-	0.8891	88.91%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.7055	70.55%
Fish aquatic toxicity	+	1.0000	100.00%

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	97.47%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.06%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.40%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.89%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.61%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.27%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.53%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.13%	94.73%
CHEMBL2581	P07339	Cathepsin D	85.84%	98.95%
CHEMBL3194	P02766	Transthyretin	83.68%	90.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.10%	95.50%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.49%	91.71%

Plants that contains it

• Humulus lupulus

Cross-Links

• PubChem: 25201207
• LOTUS: LTS0002181
• wikiData: Q105031534