(3E,5S)-5-(2-methylprop-1-enyl)-3-(4-oxopentylidene)tetrahydrofuran-2-one

Details

• Internal ID: e9b5b3c0-2f81-42a2-b45a-de2c0e92f47d
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3E,5S)-5-(2-methylprop-1-enyl)-3-(4-oxopentylidene)oxolan-2-one
• SMILES (Canonical): CC(=CC1CC(=CCCC(=O)C)C(=O)O1)C
• SMILES (Isomeric): CC(=C[C@@H]1C/C(=C\CCC(=O)C)/C(=O)O1)C
• InChI: InChI=1S/C13H18O3/c1-9(2)7-12-8-11(13(15)16-12)6-4-5-10(3)14/h6-7,12H,4-5,8H2,1-3H3/b11-6+/t12-/m1/s1
• InChI Key: HAGKOYTUAINBNR-IGEMTJHASA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₈O₃
• Molecular Weight: 222.28 g/mol
• Exact Mass: 222.125594432 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.56
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• CHEMBL1077130
• (3E,5S)-5-(2-methylprop-1-enyl)-3-(4-oxopentylidene)tetrahydrofuran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9919	99.19%
Caco-2	+	0.6575	65.75%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7636	76.36%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.9268	92.68%
OATP1B3 inhibitior	+	0.9110	91.10%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	-	0.7087	70.87%
P-glycoprotein inhibitior	-	0.9593	95.93%
P-glycoprotein substrate	-	0.9163	91.63%
CYP3A4 substrate	-	0.5442	54.42%
CYP2C9 substrate	-	0.8108	81.08%
CYP2D6 substrate	-	0.9004	90.04%
CYP3A4 inhibition	-	0.7998	79.98%
CYP2C9 inhibition	-	0.8560	85.60%
CYP2C19 inhibition	-	0.7154	71.54%
CYP2D6 inhibition	-	0.9242	92.42%
CYP1A2 inhibition	-	0.6121	61.21%
CYP2C8 inhibition	-	0.9653	96.53%
CYP inhibitory promiscuity	-	0.8396	83.96%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9128	91.28%
Carcinogenicity (trinary)	Non-required	0.6585	65.85%
Eye corrosion	-	0.9422	94.22%
Eye irritation	+	0.6728	67.28%
Skin irritation	+	0.5477	54.77%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8359	83.59%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	+	0.5482	54.82%
skin sensitisation	-	0.5838	58.38%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	-	0.7333	73.33%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	+	0.5134	51.34%
Acute Oral Toxicity (c)	III	0.6676	66.76%
Estrogen receptor binding	-	0.7966	79.66%
Androgen receptor binding	-	0.8003	80.03%
Thyroid receptor binding	-	0.8456	84.56%
Glucocorticoid receptor binding	-	0.6803	68.03%
Aromatase binding	-	0.7774	77.74%
PPAR gamma	-	0.7965	79.65%
Honey bee toxicity	-	0.8135	81.35%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9882	98.82%

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	91.54%	91.11%
CHEMBL2581	P07339	Cathepsin D	87.61%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.91%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.16%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.98%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.84%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.12%	95.56%

Plants that contains it

• Heteroplexis microcephala

Cross-Links

• PubChem: 44179793
• LOTUS: LTS0184731
• wikiData: Q105024868