Licobichalcone

Details

• Internal ID: fd313a31-b807-45bd-bf92-701601253d5b
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: [(1S,2S)-1-(3,4-dihydroxy-2-methoxyphenyl)-6,7-dihydroxy-3-(4-hydroxybenzoyl)-8-methoxy-1,2-dihydronaphthalen-2-yl]-(4-hydroxyphenyl)methanone
• SMILES (Canonical): COC1=C(C=CC(=C1O)O)C2C(C(=CC3=CC(=C(C(=C23)OC)O)O)C(=O)C4=CC=C(C=C4)O)C(=O)C5=CC=C(C=C5)O
• SMILES (Isomeric): COC1=C(C=CC(=C1O)O)[C@@H]2[C@@H](C(=CC3=CC(=C(C(=C23)OC)O)O)C(=O)C4=CC=C(C=C4)O)C(=O)C5=CC=C(C=C5)O
• InChI: InChI=1S/C32H26O10/c1-41-31-20(11-12-22(35)29(31)39)25-24-17(14-23(36)30(40)32(24)42-2)13-21(27(37)15-3-7-18(33)8-4-15)26(25)28(38)16-5-9-19(34)10-6-16/h3-14,25-26,33-36,39-40H,1-2H3/t25-,26+/m0/s1
• InChI Key: WJSPTHUPUYBNNI-IZZNHLLZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₂₆O₁₀
• Molecular Weight: 570.50 g/mol
• Exact Mass: 570.15259702 g/mol
• Topological Polar Surface Area (TPSA): 174.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.85
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

• [(1S,2S)-1-(3,4-dihydroxy-2-methoxyphenyl)-6,7-dihydroxy-3-(4-hydroxybenzoyl)-8-methoxy-1,2-dihydronaphthalen-2-yl]-(4-hydroxyphenyl)methanone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9914	99.14%
Caco-2	-	0.8068	80.68%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8145	81.45%
OATP2B1 inhibitior	-	0.5735	57.35%
OATP1B1 inhibitior	+	0.8832	88.32%
OATP1B3 inhibitior	+	0.9529	95.29%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8307	83.07%
P-glycoprotein inhibitior	+	0.7567	75.67%
P-glycoprotein substrate	-	0.6150	61.50%
CYP3A4 substrate	+	0.6284	62.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7775	77.75%
CYP3A4 inhibition	-	0.6933	69.33%
CYP2C9 inhibition	+	0.8325	83.25%
CYP2C19 inhibition	+	0.5767	57.67%
CYP2D6 inhibition	-	0.8267	82.67%
CYP1A2 inhibition	+	0.8521	85.21%
CYP2C8 inhibition	+	0.9453	94.53%
CYP inhibitory promiscuity	+	0.6560	65.60%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8917	89.17%
Carcinogenicity (trinary)	Non-required	0.5333	53.33%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.7514	75.14%
Skin irritation	-	0.6806	68.06%
Skin corrosion	-	0.9335	93.35%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7840	78.40%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.5323	53.23%
skin sensitisation	-	0.7718	77.18%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8112	81.12%
Acute Oral Toxicity (c)	III	0.4099	40.99%
Estrogen receptor binding	+	0.8351	83.51%
Androgen receptor binding	+	0.8087	80.87%
Thyroid receptor binding	+	0.5656	56.56%
Glucocorticoid receptor binding	+	0.6933	69.33%
Aromatase binding	-	0.7176	71.76%
PPAR gamma	+	0.6748	67.48%
Honey bee toxicity	-	0.8719	87.19%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9958	99.58%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	36200 nM	IC50	PMID: 24047800

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.58%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.70%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.98%	86.33%
CHEMBL2535	P11166	Glucose transporter	92.32%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.25%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	87.52%	91.19%
CHEMBL3194	P02766	Transthyretin	86.20%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	85.99%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.48%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.33%	99.15%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	84.22%	85.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.72%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.52%	95.89%
CHEMBL1255126	O15151	Protein Mdm4	83.43%	90.20%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.71%	90.71%
CHEMBL4208	P20618	Proteasome component C5	81.04%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.00%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.78%	85.14%

Plants that contains it

• Glycyrrhiza uralensis
• Glycyrrhiza uralensis
• Mitracarpus hirtus

Cross-Links

• PubChem: 11827914
• NPASS: NPC149389
• ChEMBL: CHEMBL2437364
• LOTUS: LTS0235238
• wikiData: Q105307059