Eupenoxide

Details

• Internal ID: be0fa238-f8ca-4e93-97ea-83455fd295c5
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Secondary alcohols
• IUPAC Name: (1S,2R,5S,6R)-3-[(E)-hept-1-enyl]-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol
• SMILES (Canonical): CCCCCC=CC1=C(C(C2C(C1O)O2)O)CO
• SMILES (Isomeric): CCCCC/C=C/C1=C([C@@H]([C@@H]2[C@H]([C@@H]1O)O2)O)CO
• InChI: InChI=1S/C14H22O4/c1-2-3-4-5-6-7-9-10(8-15)12(17)14-13(18-14)11(9)16/h6-7,11-17H,2-5,8H2,1H3/b7-6+/t11-,12+,13+,14-/m1/s1
• InChI Key: CBWMFTMZESYHBT-KWUVHTBZSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₂O₄
• Molecular Weight: 254.32 g/mol
• Exact Mass: 254.15180918 g/mol
• Topological Polar Surface Area (TPSA): 73.20 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.91
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• (+)-Eupenoxide
• MMD39WDE3N
• UNII-MMD39WDE3N
• 873843-69-7
• (1R,2S,5R,6S)-4-(1E)-1-Hepten-1-yl-3-(hydroxymethyl)-7-oxabicyclo(4.1.0)hept-3-ene-2,5-diol
• 7-Oxabicyclo(4.1.0)hept-3-ene-2,5-diol, 3-(1E)-1-heptenyl-4-(hydroxymethyl)-, (1R,2S,5R,6S)-
• 7-Oxabicyclo(4.1.0)hept-3-ene-2,5-diol, 4-(1E)-1-hepten-1-yl-3-(hydroxymethyl)-, (1R,2S,5R,6S)-
• (1S,2R,5S,6R)-3-[(E)-hept-1-enyl]-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol
• CHEMBL3286755

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8880	88.80%
Caco-2	-	0.6937	69.37%
Blood Brain Barrier	+	0.5299	52.99%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.4683	46.83%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.7202	72.02%
OATP1B3 inhibitior	+	0.9493	94.93%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.5922	59.22%
BSEP inhibitior	-	0.9310	93.10%
P-glycoprotein inhibitior	-	0.9345	93.45%
P-glycoprotein substrate	-	0.8525	85.25%
CYP3A4 substrate	-	0.5504	55.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7585	75.85%
CYP3A4 inhibition	-	0.7533	75.33%
CYP2C9 inhibition	-	0.7758	77.58%
CYP2C19 inhibition	-	0.7436	74.36%
CYP2D6 inhibition	-	0.8179	81.79%
CYP1A2 inhibition	-	0.7658	76.58%
CYP2C8 inhibition	-	0.8774	87.74%
CYP inhibitory promiscuity	-	0.5905	59.05%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6367	63.67%
Eye corrosion	-	0.9781	97.81%
Eye irritation	-	0.9704	97.04%
Skin irritation	-	0.6294	62.94%
Skin corrosion	-	0.9278	92.78%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.7369	73.69%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	+	0.5167	51.67%
Acute Oral Toxicity (c)	III	0.5926	59.26%
Estrogen receptor binding	+	0.5299	52.99%
Androgen receptor binding	-	0.7360	73.60%
Thyroid receptor binding	+	0.5749	57.49%
Glucocorticoid receptor binding	+	0.5482	54.82%
Aromatase binding	-	0.7728	77.28%
PPAR gamma	+	0.5316	53.16%
Honey bee toxicity	-	0.9519	95.19%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5992	59.92%
Fish aquatic toxicity	+	0.9152	91.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	94.19%	99.17%
CHEMBL2581	P07339	Cathepsin D	91.96%	98.95%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	91.18%	92.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.08%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.75%	91.11%
CHEMBL230	P35354	Cyclooxygenase-2	90.26%	89.63%
CHEMBL3401	O75469	Pregnane X receptor	89.64%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.18%	97.25%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.36%	96.95%

Plants that contains it

• Uncaria sinensis

Cross-Links

• PubChem: 11242243
• NPASS: NPC24590