Lophirone A

Details

• Internal ID: 512ab26c-a4d8-4579-b93c-ca24701adce8
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 2-Hydroxy-dihydrochalcones
• IUPAC Name: 3-[1-(2,4-dihydroxyphenyl)-3,3-bis(4-hydroxyphenyl)-1-oxopropan-2-yl]-7-hydroxychromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C(C2=CC=C(C=C2)O)C(C3=COC4=C(C3=O)C=CC(=C4)O)C(=O)C5=C(C=C(C=C5)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C(C2=CC=C(C=C2)O)C(C3=COC4=C(C3=O)C=CC(=C4)O)C(=O)C5=C(C=C(C=C5)O)O)O
• InChI: InChI=1S/C30H22O8/c31-18-5-1-16(2-6-18)27(17-3-7-19(32)8-4-17)28(30(37)22-11-9-20(33)13-25(22)35)24-15-38-26-14-21(34)10-12-23(26)29(24)36/h1-15,27-28,31-35H
• InChI Key: ZPIXFZZVVJUNDO-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₂O₈
• Molecular Weight: 510.50 g/mol
• Exact Mass: 510.13146766 g/mol
• Topological Polar Surface Area (TPSA): 145.00 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 5.12
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• 110383-39-6
• 3-[1-(2,4-dihydroxyphenyl)-3,3-bis(4-hydroxyphenyl)-1-oxopropan-2-yl]-7-hydroxychromen-4-one
• CCRIS 5445
• DTXSID80911620
• 3-[1-(2,4-Dihydroxyphenyl)-3,3-bis(4-hydroxyphenyl)-1-oxopropan-2-yl]-7-hydroxy-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9254	92.54%
Caco-2	-	0.8300	83.00%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6878	68.78%
OATP2B1 inhibitior	+	0.5653	56.53%
OATP1B1 inhibitior	+	0.8949	89.49%
OATP1B3 inhibitior	+	0.8480	84.80%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7931	79.31%
P-glycoprotein inhibitior	-	0.6559	65.59%
P-glycoprotein substrate	-	0.7087	70.87%
CYP3A4 substrate	+	0.5101	51.01%
CYP2C9 substrate	+	0.6107	61.07%
CYP2D6 substrate	-	0.8410	84.10%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	+	0.7662	76.62%
CYP2C19 inhibition	+	0.5283	52.83%
CYP2D6 inhibition	-	0.9010	90.10%
CYP1A2 inhibition	+	0.8537	85.37%
CYP2C8 inhibition	+	0.4493	44.93%
CYP inhibitory promiscuity	-	0.5575	55.75%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7132	71.32%
Eye corrosion	-	0.9895	98.95%
Eye irritation	+	0.6143	61.43%
Skin irritation	+	0.6174	61.74%
Skin corrosion	-	0.9517	95.17%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	-	0.6002	60.02%
skin sensitisation	-	0.8226	82.26%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7981	79.81%
Acute Oral Toxicity (c)	II	0.5237	52.37%
Estrogen receptor binding	+	0.8042	80.42%
Androgen receptor binding	+	0.9046	90.46%
Thyroid receptor binding	+	0.5533	55.33%
Glucocorticoid receptor binding	+	0.7968	79.68%
Aromatase binding	-	0.5608	56.08%
PPAR gamma	+	0.8575	85.75%
Honey bee toxicity	-	0.7758	77.58%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9266	92.66%

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	99.32%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.46%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.77%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.63%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.41%	95.56%
CHEMBL2535	P11166	Glucose transporter	87.61%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.05%	99.15%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.77%	93.40%
CHEMBL3194	P02766	Transthyretin	83.74%	90.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.52%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	81.84%	94.73%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.40%	93.65%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.33%	85.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.39%	99.17%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.11%	96.12%

Plants that contains it

• Campylospermum flavum
• Campylospermum glaucum
• Campylospermum sulcatum
• Lophira alata
• Lophira lanceolata
• Ochna afzelii
• Ochna calodendron
• Ochna integerrima

Cross-Links

• PubChem: 5488805
• LOTUS: LTS0223496
• wikiData: Q82881769