5-hydroxy-2,2-dimethyl-3H-pyrano[3,2-g]chromene-4,8-dione

Details

• Internal ID: b0411065-8094-4986-a7ee-f2af5e984d3d
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Linear pyranocoumarins
• IUPAC Name: 5-hydroxy-2,2-dimethyl-3H-pyrano[3,2-g]chromene-4,8-dione
• SMILES (Canonical): CC1(CC(=O)C2=C(O1)C=C3C(=C2O)C=CC(=O)O3)C
• SMILES (Isomeric): CC1(CC(=O)C2=C(O1)C=C3C(=C2O)C=CC(=O)O3)C
• InChI: InChI=1S/C14H12O5/c1-14(2)6-8(15)12-10(19-14)5-9-7(13(12)17)3-4-11(16)18-9/h3-5,17H,6H2,1-2H3
• InChI Key: XFSINVCSJTYZGH-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₅
• Molecular Weight: 260.24 g/mol
• Exact Mass: 260.06847348 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.24
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 17276-27-6
• 5-hydroxy-2,2-dimethyl-3H-pyrano[3,2-g]chromene-4,8-dione
• DTXSID40415694
• NSC155356
• AKOS040740326
• NSC-155356

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9488	94.88%
Caco-2	+	0.6954	69.54%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7707	77.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8686	86.86%
OATP1B3 inhibitior	+	0.9752	97.52%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8039	80.39%
P-glycoprotein inhibitior	-	0.8814	88.14%
P-glycoprotein substrate	-	0.8060	80.60%
CYP3A4 substrate	+	0.5222	52.22%
CYP2C9 substrate	+	0.8398	83.98%
CYP2D6 substrate	-	0.8502	85.02%
CYP3A4 inhibition	-	0.7914	79.14%
CYP2C9 inhibition	+	0.5585	55.85%
CYP2C19 inhibition	-	0.8899	88.99%
CYP2D6 inhibition	-	0.8617	86.17%
CYP1A2 inhibition	-	0.8688	86.88%
CYP2C8 inhibition	-	0.6933	69.33%
CYP inhibitory promiscuity	-	0.9469	94.69%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9713	97.13%
Carcinogenicity (trinary)	Non-required	0.5813	58.13%
Eye corrosion	-	0.9882	98.82%
Eye irritation	+	0.7643	76.43%
Skin irritation	-	0.7379	73.79%
Skin corrosion	-	0.9231	92.31%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6809	68.09%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8520	85.20%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7116	71.16%
Acute Oral Toxicity (c)	III	0.4661	46.61%
Estrogen receptor binding	+	0.8916	89.16%
Androgen receptor binding	+	0.7891	78.91%
Thyroid receptor binding	-	0.5990	59.90%
Glucocorticoid receptor binding	+	0.7487	74.87%
Aromatase binding	+	0.6877	68.77%
PPAR gamma	+	0.6462	64.62%
Honey bee toxicity	-	0.8911	89.11%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9612	96.12%

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	99.65%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.85%	94.45%
CHEMBL2581	P07339	Cathepsin D	96.05%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.51%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.15%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.19%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.56%	94.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.89%	85.30%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.88%	90.71%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	81.53%	94.42%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.93%	85.11%

Plants that contains it

• Clausena excavata
• Clausena heptaphylla
• Clausena indica

Cross-Links

• PubChem: 5315948
• NPASS: NPC304935
• LOTUS: LTS0147829
• wikiData: Q82224667