Lopac-I-3766

Details

• Internal ID: 3a607276-c07c-470a-aeee-c80fd0e2fe72
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 2-Hydroxychalcones
• IUPAC Name: (Z)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)C2=C(C=C(C=C2)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C\C(=O)C2=C(C=C(C=C2)O)O)O
• InChI: InChI=1S/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3-
• InChI Key: DXDRHHKMWQZJHT-BAQGIRSFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₄
• Molecular Weight: 256.25 g/mol
• Exact Mass: 256.07355886 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.70
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• CHEMBL1395334
• NCGC00015556-01

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9856	98.56%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7711	77.11%
OATP2B1 inhibitior	-	0.7039	70.39%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9838	98.38%
BSEP inhibitior	-	0.6574	65.74%
P-glycoprotein inhibitior	-	0.9385	93.85%
P-glycoprotein substrate	-	0.9513	95.13%
CYP3A4 substrate	-	0.6718	67.18%
CYP2C9 substrate	-	0.6211	62.11%
CYP2D6 substrate	-	0.8534	85.34%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9350	93.50%
CYP2C8 inhibition	+	0.5638	56.38%
CYP inhibitory promiscuity	+	0.8559	85.59%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7472	74.72%
Carcinogenicity (trinary)	Non-required	0.7048	70.48%
Eye corrosion	-	0.9801	98.01%
Eye irritation	+	0.9919	99.19%
Skin irritation	+	0.6928	69.28%
Skin corrosion	-	0.9313	93.13%
Ames mutagenesis	+	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8554	85.54%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.8967	89.67%
skin sensitisation	+	0.8772	87.72%
Respiratory toxicity	-	0.7444	74.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.6477	64.77%
Acute Oral Toxicity (c)	III	0.7921	79.21%
Estrogen receptor binding	+	0.9293	92.93%
Androgen receptor binding	+	0.8927	89.27%
Thyroid receptor binding	+	0.6737	67.37%
Glucocorticoid receptor binding	+	0.8590	85.90%
Aromatase binding	+	0.9380	93.80%
PPAR gamma	+	0.9077	90.77%
Honey bee toxicity	-	0.9037	90.37%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9906	99.06%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1900	P15121	Aldose reductase	320 nM	IC50	via Super-PRED
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	25118.9 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	31622.8 nM	Potency	via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	5011.87 nM	AC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	12589.25 nM	AC50	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	19952.6 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	15848.9 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	3162.3 nM; 3162.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	10000 nM	Potency	via CMAUP
CHEMBL2789	P37059	Estradiol 17-beta-dehydrogenase 2	360 nM	IC50	via Super-PRED
CHEMBL242	Q92731	Estrogen receptor beta	269 nM	IC50	via Super-PRED
CHEMBL4040	P28482	MAP kinase ERK2	251.2 nM; 251.2 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	3162.3 nM; 3162.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	3162.3 nM; 3162.3 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.99%	91.11%
CHEMBL3194	P02766	Transthyretin	95.74%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.11%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.29%	86.33%
CHEMBL1929	P47989	Xanthine dehydrogenase	86.52%	96.12%
CHEMBL4208	P20618	Proteasome component C5	84.79%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.31%	89.00%
CHEMBL2581	P07339	Cathepsin D	83.16%	98.95%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.41%	91.71%
CHEMBL2535	P11166	Glucose transporter	81.12%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.84%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.48%	95.50%

Plants that contains it

• Cicer arietinum
• Dracaena draco
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Glycyrrhiza yunnanensis
• Onobrychis viciifolia
• Robinia pseudoacacia
• Sophora tomentosa
• Spatholobus suberectus

Cross-Links

• PubChem: 6603886
• NPASS: NPC115159
• ChEMBL: CHEMBL1395334