1,7-bis(4-Hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one

Details

• Internal ID: e719ad60-0e26-4ed6-bd6f-328b8f3a4927
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: 1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC=CC(=O)C=CC2=CC(=C(C=C2)O)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C=CC=CC(=O)C=CC2=CC(=C(C=C2)O)OC)O
• InChI: InChI=1S/C21H20O5/c1-25-20-13-15(8-11-18(20)23)5-3-4-6-17(22)10-7-16-9-12-19(24)21(14-16)26-2/h3-14,23-24H,1-2H3
• InChI Key: JUDCTVXWYFNGQQ-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₅
• Molecular Weight: 352.40 g/mol
• Exact Mass: 352.13107373 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.97
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• CHEBI:176653
• 1,7-bis(4-hydr oxy -3 methoxy phenyl) -1,4,6-heptatrien-3-one?

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9908	99.08%
Caco-2	-	0.5966	59.66%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8429	84.29%
OATP2B1 inhibitior	-	0.7117	71.17%
OATP1B1 inhibitior	+	0.9365	93.65%
OATP1B3 inhibitior	+	0.9614	96.14%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8850	88.50%
P-glycoprotein inhibitior	+	0.6346	63.46%
P-glycoprotein substrate	-	0.9527	95.27%
CYP3A4 substrate	-	0.5725	57.25%
CYP2C9 substrate	+	0.6043	60.43%
CYP2D6 substrate	-	0.8167	81.67%
CYP3A4 inhibition	+	0.5099	50.99%
CYP2C9 inhibition	+	0.6137	61.37%
CYP2C19 inhibition	+	0.9009	90.09%
CYP2D6 inhibition	-	0.8085	80.85%
CYP1A2 inhibition	+	0.8965	89.65%
CYP2C8 inhibition	+	0.6400	64.00%
CYP inhibitory promiscuity	+	0.7635	76.35%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.7642	76.42%
Carcinogenicity (trinary)	Non-required	0.6112	61.12%
Eye corrosion	-	0.9492	94.92%
Eye irritation	+	0.8732	87.32%
Skin irritation	-	0.6390	63.90%
Skin corrosion	-	0.9639	96.39%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6467	64.67%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	-	0.7553	75.53%
skin sensitisation	-	0.7776	77.76%
Respiratory toxicity	-	0.9000	90.00%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.8125	81.25%
Nephrotoxicity	-	0.7397	73.97%
Acute Oral Toxicity (c)	III	0.6654	66.54%
Estrogen receptor binding	+	0.8600	86.00%
Androgen receptor binding	+	0.8294	82.94%
Thyroid receptor binding	+	0.7882	78.82%
Glucocorticoid receptor binding	+	0.8876	88.76%
Aromatase binding	+	0.7954	79.54%
PPAR gamma	+	0.8109	81.09%
Honey bee toxicity	-	0.9317	93.17%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5245	52.45%
Fish aquatic toxicity	+	0.9872	98.72%

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	97.36%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.77%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.91%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.54%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.31%	95.56%
CHEMBL3194	P02766	Transthyretin	92.67%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.94%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.66%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.43%	89.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.30%	95.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.20%	99.15%
CHEMBL4208	P20618	Proteasome component C5	81.69%	90.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.28%	80.78%

Plants that contains it

• Curcuma longa

Cross-Links

• PubChem: 85309552
• LOTUS: LTS0240194
• wikiData: Q105135164