(E)-1-[(2S,3S)-4-methylidene-5-oxo-3-(3-oxobutyl)oxolan-2-yl]hex-3-ene-2,5-dione

Details

• Internal ID: 08d19542-e73d-41b0-acd9-83b384214721
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (E)-1-[(2S,3S)-4-methylidene-5-oxo-3-(3-oxobutyl)oxolan-2-yl]hex-3-ene-2,5-dione
• SMILES (Canonical): CC(=O)CCC1C(OC(=O)C1=C)CC(=O)C=CC(=O)C
• SMILES (Isomeric): CC(=O)CC[C@@H]1[C@@H](OC(=O)C1=C)CC(=O)/C=C/C(=O)C
• InChI: InChI=1S/C15H18O5/c1-9(16)4-6-12(18)8-14-13(7-5-10(2)17)11(3)15(19)20-14/h4,6,13-14H,3,5,7-8H2,1-2H3/b6-4+/t13-,14-/m0/s1
• InChI Key: VNOAOFGIURPXMV-HHAVJRIZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 77.50 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 1.56
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 7

Synonyms

• 102907-31-3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9819	98.19%
Caco-2	-	0.6188	61.88%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7234	72.34%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.8882	88.82%
OATP1B3 inhibitior	+	0.9074	90.74%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.7682	76.82%
P-glycoprotein inhibitior	-	0.8157	81.57%
P-glycoprotein substrate	-	0.8966	89.66%
CYP3A4 substrate	+	0.5098	50.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8875	88.75%
CYP3A4 inhibition	-	0.8215	82.15%
CYP2C9 inhibition	-	0.9094	90.94%
CYP2C19 inhibition	-	0.7983	79.83%
CYP2D6 inhibition	-	0.9288	92.88%
CYP1A2 inhibition	-	0.5778	57.78%
CYP2C8 inhibition	-	0.8833	88.33%
CYP inhibitory promiscuity	-	0.8873	88.73%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8728	87.28%
Carcinogenicity (trinary)	Non-required	0.6981	69.81%
Eye corrosion	-	0.9042	90.42%
Eye irritation	-	0.5950	59.50%
Skin irritation	+	0.5265	52.65%
Skin corrosion	-	0.9241	92.41%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3938	39.38%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	+	0.6339	63.39%
skin sensitisation	-	0.7947	79.47%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	-	0.6444	64.44%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	+	0.6009	60.09%
Acute Oral Toxicity (c)	III	0.6567	65.67%
Estrogen receptor binding	-	0.5963	59.63%
Androgen receptor binding	-	0.5950	59.50%
Thyroid receptor binding	-	0.7853	78.53%
Glucocorticoid receptor binding	-	0.5702	57.02%
Aromatase binding	-	0.8489	84.89%
PPAR gamma	-	0.6555	65.55%
Honey bee toxicity	-	0.7993	79.93%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9931	99.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.39%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.23%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.17%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.06%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.02%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	83.87%	94.73%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.56%	89.34%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.32%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.98%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.70%	85.14%

Plants that contains it

• Artemisia xanthochroa
• Azolla pinnata subsp. asiatica
• Cyperus haspan
• Goniothalamus thwaitesii

Cross-Links

• PubChem: 101317829
• NPASS: NPC115168
• LOTUS: LTS0116225
• wikiData: Q105289765