(1R,5S)-5-hydroxy-4,7,7-trimethyl-8-oxabicyclo[3.2.1]oct-3-en-2-one

Details

• Internal ID: 1b6ecd0e-c845-4e33-a82a-784e11b5edbd
• Taxonomy: Organoheterocyclic compounds > Pyrans > Pyranones and derivatives > Dihydropyranones
• IUPAC Name: (1R,5S)-5-hydroxy-4,7,7-trimethyl-8-oxabicyclo[3.2.1]oct-3-en-2-one
• SMILES (Canonical): CC1=CC(=O)C2C(CC1(O2)O)(C)C
• SMILES (Isomeric): CC1=CC(=O)[C@H]2C(C[C@@]1(O2)O)(C)C
• InChI: InChI=1S/C10H14O3/c1-6-4-7(11)8-9(2,3)5-10(6,12)13-8/h4,8,12H,5H2,1-3H3/t8-,10-/m0/s1
• InChI Key: SRBSXGSWXUVKPY-WPRPVWTQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄O₃
• Molecular Weight: 182.22 g/mol
• Exact Mass: 182.094294304 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.02
• H-Bond Acceptor: 3
• 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	+	0.9896	98.96%
Caco-2	+	0.8169	81.69%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6633	66.33%
OATP2B1 inhibitior	-	0.8548	85.48%
OATP1B1 inhibitior	+	0.9294	92.94%
OATP1B3 inhibitior	+	0.9642	96.42%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9582	95.82%
P-glycoprotein inhibitior	-	0.9669	96.69%
P-glycoprotein substrate	-	0.9578	95.78%
CYP3A4 substrate	-	0.5270	52.70%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8732	87.32%
CYP3A4 inhibition	-	0.8736	87.36%
CYP2C9 inhibition	-	0.9308	93.08%
CYP2C19 inhibition	-	0.8745	87.45%
CYP2D6 inhibition	-	0.9226	92.26%
CYP1A2 inhibition	-	0.8366	83.66%
CYP2C8 inhibition	-	0.9706	97.06%
CYP inhibitory promiscuity	-	0.9401	94.01%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9317	93.17%
Carcinogenicity (trinary)	Non-required	0.5512	55.12%
Eye corrosion	-	0.9763	97.63%
Eye irritation	+	0.5550	55.50%
Skin irritation	+	0.5305	53.05%
Skin corrosion	-	0.8059	80.59%
Ames mutagenesis	-	0.5254	52.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7076	70.76%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.6275	62.75%
skin sensitisation	+	0.5177	51.77%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.6934	69.34%
Acute Oral Toxicity (c)	III	0.5797	57.97%
Estrogen receptor binding	-	0.8679	86.79%
Androgen receptor binding	+	0.5292	52.92%
Thyroid receptor binding	-	0.8112	81.12%
Glucocorticoid receptor binding	-	0.8286	82.86%
Aromatase binding	-	0.8217	82.17%
PPAR gamma	-	0.7461	74.61%
Honey bee toxicity	-	0.9452	94.52%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8584	85.84%

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	95.82%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.35%	95.56%
CHEMBL230	P35354	Cyclooxygenase-2	87.96%	89.63%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.93%	96.09%
CHEMBL2581	P07339	Cathepsin D	85.12%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.64%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.67%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.87%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.10%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.34%	85.14%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	80.26%	86.00%

Plants that contains it

• Asarum sieboldii

Cross-Links

• PubChem: 101663468
• LOTUS: LTS0013678
• wikiData: Q105258885