(10R)-5,10-dihydroxy-8,8-dimethyl-9,10-dihydropyrano[2,3-f]chromen-2-one

Details

• Internal ID: 4e124384-bb5e-423f-b31a-9dd92997997a
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: (10R)-5,10-dihydroxy-8,8-dimethyl-9,10-dihydropyrano[2,3-f]chromen-2-one
• SMILES (Canonical): CC1(CC(C2=C(O1)C=C(C3=C2OC(=O)C=C3)O)O)C
• SMILES (Isomeric): CC1(C[C@H](C2=C(O1)C=C(C3=C2OC(=O)C=C3)O)O)C
• InChI: InChI=1S/C14H14O5/c1-14(2)6-9(16)12-10(19-14)5-8(15)7-3-4-11(17)18-13(7)12/h3-5,9,15-16H,6H2,1-2H3/t9-/m1/s1
• InChI Key: WWQXVXLXRABEDZ-SECBINFHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₅
• Molecular Weight: 262.26 g/mol
• Exact Mass: 262.08412354 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.09
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9800	98.00%
Caco-2	+	0.6060	60.60%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7318	73.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9152	91.52%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7721	77.21%
P-glycoprotein inhibitior	-	0.8819	88.19%
P-glycoprotein substrate	-	0.7765	77.65%
CYP3A4 substrate	+	0.5328	53.28%
CYP2C9 substrate	-	0.6233	62.33%
CYP2D6 substrate	-	0.7813	78.13%
CYP3A4 inhibition	-	0.8508	85.08%
CYP2C9 inhibition	-	0.7428	74.28%
CYP2C19 inhibition	-	0.9049	90.49%
CYP2D6 inhibition	-	0.8311	83.11%
CYP1A2 inhibition	-	0.7972	79.72%
CYP2C8 inhibition	-	0.7451	74.51%
CYP inhibitory promiscuity	-	0.9460	94.60%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.5723	57.23%
Eye corrosion	-	0.9898	98.98%
Eye irritation	+	0.7559	75.59%
Skin irritation	-	0.7351	73.51%
Skin corrosion	-	0.9472	94.72%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7514	75.14%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.5330	53.30%
skin sensitisation	-	0.8002	80.02%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7092	70.92%
Acute Oral Toxicity (c)	III	0.7380	73.80%
Estrogen receptor binding	+	0.8112	81.12%
Androgen receptor binding	+	0.7732	77.32%
Thyroid receptor binding	+	0.5489	54.89%
Glucocorticoid receptor binding	+	0.8870	88.70%
Aromatase binding	+	0.6363	63.63%
PPAR gamma	+	0.6608	66.08%
Honey bee toxicity	-	0.8857	88.57%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9219	92.19%

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	99.03%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.07%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.36%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.28%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.28%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	89.52%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.26%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.92%	93.99%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.08%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.87%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.69%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.27%	90.71%

Plants that contains it

• Citrus × aurantium

Cross-Links

• PubChem: 163050546
• LOTUS: LTS0198465
• wikiData: Q105314226