Lachnanthopyrone

Details

• Internal ID: 98edad51-915a-45d2-bb42-06a10b7feffe
• Taxonomy: Phenylpropanoids and polyketides > Isocoumarins and derivatives
• IUPAC Name: 7-hydroxy-10-phenyl-3-oxatricyclo[7.3.1.05,13]trideca-1(13),4,6,9,11-pentaene-2,8-dione
• SMILES (Canonical): C1=CC=C(C=C1)C2=C3C4=C(C=C2)C(=O)OC=C4C=C(C3=O)O
• SMILES (Isomeric): C1=CC=C(C=C1)C2=C3C4=C(C=C2)C(=O)OC=C4C=C(C3=O)O
• InChI: InChI=1S/C18H10O4/c19-14-8-11-9-22-18(21)13-7-6-12(10-4-2-1-3-5-10)16(15(11)13)17(14)20/h1-9,19H
• InChI Key: TUROAXCIAPETPG-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₀O₄
• Molecular Weight: 290.30 g/mol
• Exact Mass: 290.05790880 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.56
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 37011-64-6
• NSC154708
• CHEMBL4279037
• DTXSID70302861
• NSC-154708
• 5-Hydroxy-7-phenyl-benzo[de]isochromene-1,6-dione
• 5-hydroxy-7-phenyl-1H,6H-benzo[de]isochromene-1,6-dione
• 1H,6H-naphtho[1,8-cd]pyran-1,6-dione, 5-hydroxy-7-phenyl-
• InChI=1/C18H10O4/c19-14-8-11-9-22-18(21)13-7-6-12(10-4-2-1-3-5-10)16(15(11)13)17(14)20/h1-9,19

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9847	98.47%
Caco-2	-	0.5923	59.23%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7695	76.95%
OATP2B1 inhibitior	-	0.7185	71.85%
OATP1B1 inhibitior	+	0.9108	91.08%
OATP1B3 inhibitior	+	0.9472	94.72%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5780	57.80%
P-glycoprotein inhibitior	-	0.8319	83.19%
P-glycoprotein substrate	-	0.8633	86.33%
CYP3A4 substrate	+	0.5102	51.02%
CYP2C9 substrate	-	0.8259	82.59%
CYP2D6 substrate	-	0.8705	87.05%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	+	0.8785	87.85%
CYP2C19 inhibition	-	0.6460	64.60%
CYP2D6 inhibition	-	0.9200	92.00%
CYP1A2 inhibition	-	0.7786	77.86%
CYP2C8 inhibition	+	0.5072	50.72%
CYP inhibitory promiscuity	-	0.6185	61.85%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5227	52.27%
Eye corrosion	-	0.9901	99.01%
Eye irritation	+	0.6836	68.36%
Skin irritation	+	0.5674	56.74%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.5882	58.82%
Human Ether-a-go-go-Related Gene inhibition	-	0.8209	82.09%
Micronuclear	+	0.8559	85.59%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.7525	75.25%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.5698	56.98%
Acute Oral Toxicity (c)	II	0.5559	55.59%
Estrogen receptor binding	+	0.8705	87.05%
Androgen receptor binding	+	0.8947	89.47%
Thyroid receptor binding	-	0.5200	52.00%
Glucocorticoid receptor binding	+	0.8903	89.03%
Aromatase binding	+	0.8009	80.09%
PPAR gamma	+	0.9306	93.06%
Honey bee toxicity	-	0.8076	80.76%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9912	99.12%

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	98.29%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.92%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	97.74%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.48%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.98%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.56%	89.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	86.52%	96.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.17%	86.33%

Plants that contains it

• Xiphidium caeruleum

Cross-Links

• PubChem: 290627
• LOTUS: LTS0052046
• wikiData: Q82047904