(4R)-5-hydroxy-4,8,8-trimethyl-9,10-dihydro-4H-pyrano[4,3-f]chromene-2,6-dione

Details

• Internal ID: b55a658f-ec99-4154-86c0-950b1e4d89f6
• Taxonomy: Organoheterocyclic compounds > Pyrans > Pyranones and derivatives > Dihydropyranones
• IUPAC Name: (4R)-5-hydroxy-4,8,8-trimethyl-9,10-dihydro-4H-pyrano[4,3-f]chromene-2,6-dione
• SMILES (Canonical): CC1C2=C(C(=O)C3=C(C2=CC(=O)O1)CCC(O3)(C)C)O
• SMILES (Isomeric): C[C@@H]1C2=C(C(=O)C3=C(C2=CC(=O)O1)CCC(O3)(C)C)O
• InChI: InChI=1S/C15H16O5/c1-7-11-9(6-10(16)19-7)8-4-5-15(2,3)20-14(8)13(18)12(11)17/h6-7,17H,4-5H2,1-3H3/t7-/m1/s1
• InChI Key: OSJKAGRXDVEZQO-SSDOTTSWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.28 g/mol
• Exact Mass: 276.09977361 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 2.10
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9783	97.83%
Caco-2	+	0.6880	68.80%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7812	78.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8613	86.13%
OATP1B3 inhibitior	+	0.9475	94.75%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.8853	88.53%
P-glycoprotein inhibitior	-	0.9156	91.56%
P-glycoprotein substrate	-	0.8807	88.07%
CYP3A4 substrate	+	0.5908	59.08%
CYP2C9 substrate	-	0.8175	81.75%
CYP2D6 substrate	-	0.8900	89.00%
CYP3A4 inhibition	-	0.7545	75.45%
CYP2C9 inhibition	-	0.9091	90.91%
CYP2C19 inhibition	-	0.9438	94.38%
CYP2D6 inhibition	-	0.8782	87.82%
CYP1A2 inhibition	-	0.8116	81.16%
CYP2C8 inhibition	-	0.8965	89.65%
CYP inhibitory promiscuity	-	0.9629	96.29%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4513	45.13%
Eye corrosion	-	0.9880	98.80%
Eye irritation	+	0.7030	70.30%
Skin irritation	+	0.5345	53.45%
Skin corrosion	-	0.8410	84.10%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6144	61.44%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.7170	71.70%
skin sensitisation	-	0.6878	68.78%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.5939	59.39%
Acute Oral Toxicity (c)	III	0.6374	63.74%
Estrogen receptor binding	+	0.7069	70.69%
Androgen receptor binding	+	0.6299	62.99%
Thyroid receptor binding	+	0.5414	54.14%
Glucocorticoid receptor binding	+	0.6759	67.59%
Aromatase binding	-	0.6334	63.34%
PPAR gamma	+	0.6233	62.33%
Honey bee toxicity	-	0.8783	87.83%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9227	92.27%

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	96.49%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	93.56%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.62%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.55%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.93%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.72%	94.45%
CHEMBL2581	P07339	Cathepsin D	84.58%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.16%	100.00%
CHEMBL2169736	O95551	Tyrosyl-DNA phosphodiesterase 2	82.75%	98.46%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.19%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	80.92%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.39%	97.09%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.15%	82.38%

Plants that contains it

• Actaea dahurica
• Lactuca serriola

Cross-Links

• PubChem: 91617751
• NPASS: NPC114268
• LOTUS: LTS0049794
• wikiData: Q105198963