(4R)-4-[(E,3S)-3-hydroxy-3-methyl-4-[(2S,4R)-4-methyl-5-oxooxolan-2-yl]but-1-enyl]-3-methylideneoxolan-2-one

Details

• Internal ID: 179e8059-82f9-4249-88b6-9cbf82085966
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (4R)-4-[(E,3S)-3-hydroxy-3-methyl-4-[(2S,4R)-4-methyl-5-oxooxolan-2-yl]but-1-enyl]-3-methylideneoxolan-2-one
• SMILES (Canonical): CC1CC(OC1=O)CC(C)(C=CC2COC(=O)C2=C)O
• SMILES (Isomeric): C[C@@H]1C[C@H](OC1=O)C[C@@](C)(/C=C/[C@H]2COC(=O)C2=C)O
• InChI: InChI=1S/C15H20O5/c1-9-6-12(20-13(9)16)7-15(3,18)5-4-11-8-19-14(17)10(11)2/h4-5,9,11-12,18H,2,6-8H2,1,3H3/b5-4+/t9-,11+,12+,15-/m1/s1
• InChI Key: WITNPNOFHCSJHE-WKXPCILHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.36
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9227	92.27%
Caco-2	-	0.5615	56.15%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7015	70.15%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.9106	91.06%
OATP1B3 inhibitior	+	0.9377	93.77%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7910	79.10%
P-glycoprotein inhibitior	-	0.9252	92.52%
P-glycoprotein substrate	-	0.6447	64.47%
CYP3A4 substrate	+	0.5856	58.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8955	89.55%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.8332	83.32%
CYP2C19 inhibition	-	0.8682	86.82%
CYP2D6 inhibition	-	0.9511	95.11%
CYP1A2 inhibition	-	0.8702	87.02%
CYP2C8 inhibition	-	0.7985	79.85%
CYP inhibitory promiscuity	-	0.9305	93.05%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8628	86.28%
Carcinogenicity (trinary)	Non-required	0.5090	50.90%
Eye corrosion	-	0.9683	96.83%
Eye irritation	-	0.8417	84.17%
Skin irritation	-	0.5650	56.50%
Skin corrosion	-	0.8566	85.66%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6162	61.62%
Micronuclear	-	0.7141	71.41%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.6450	64.50%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5864	58.64%
Estrogen receptor binding	+	0.6950	69.50%
Androgen receptor binding	-	0.5552	55.52%
Thyroid receptor binding	+	0.5814	58.14%
Glucocorticoid receptor binding	+	0.8132	81.32%
Aromatase binding	+	0.6229	62.29%
PPAR gamma	-	0.5508	55.08%
Honey bee toxicity	-	0.7999	79.99%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8857	88.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.68%	97.25%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	92.51%	90.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.13%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	89.80%	94.73%
CHEMBL2581	P07339	Cathepsin D	88.61%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.44%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.03%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.77%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.82%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.95%	97.09%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	82.74%	95.58%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.16%	90.08%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.95%	100.00%

Plants that contains it

• Anthemis auriculata

Cross-Links

• PubChem: 163106413
• LOTUS: LTS0179109
• wikiData: Q105306490