(4R,5S)-4-Acetoxy-5-[(S)-1-hydroxyethyl]-4,5-dihydrofuran-2(3H)-one

Details

• Internal ID: e82c3e52-7d81-4c02-be71-7f2028f50f6c
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: [(2S,3R)-2-[(1S)-1-hydroxyethyl]-5-oxooxolan-3-yl] acetate
• SMILES (Canonical): CC(C1C(CC(=O)O1)OC(=O)C)O
• SMILES (Isomeric): C[C@@H]([C@H]1[C@@H](CC(=O)O1)OC(=O)C)O
• InChI: InChI=1S/C8H12O5/c1-4(9)8-6(12-5(2)10)3-7(11)13-8/h4,6,8-9H,3H2,1-2H3/t4-,6+,8-/m0/s1
• InChI Key: DBLLZDYDAFRZEE-SJIRYBADSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₂O₅
• Molecular Weight: 188.18 g/mol
• Exact Mass: 188.06847348 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.39
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• (4R,5S)-4-Acetoxy-5-[(S)-1-hydroxyethyl]-4,5-dihydrofuran-2(3H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7751	77.51%
Caco-2	-	0.7777	77.77%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7829	78.29%
OATP2B1 inhibitior	-	0.8540	85.40%
OATP1B1 inhibitior	+	0.9517	95.17%
OATP1B3 inhibitior	+	0.9334	93.34%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9444	94.44%
P-glycoprotein inhibitior	-	0.9451	94.51%
P-glycoprotein substrate	-	0.9348	93.48%
CYP3A4 substrate	-	0.5355	53.55%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8627	86.27%
CYP3A4 inhibition	-	0.9238	92.38%
CYP2C9 inhibition	-	0.9163	91.63%
CYP2C19 inhibition	-	0.8531	85.31%
CYP2D6 inhibition	-	0.9512	95.12%
CYP1A2 inhibition	-	0.8672	86.72%
CYP2C8 inhibition	-	0.9827	98.27%
CYP inhibitory promiscuity	-	0.9266	92.66%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Non-required	0.6076	60.76%
Eye corrosion	-	0.8353	83.53%
Eye irritation	-	0.6461	64.61%
Skin irritation	-	0.7628	76.28%
Skin corrosion	-	0.8602	86.02%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8022	80.22%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.5925	59.25%
skin sensitisation	-	0.8888	88.88%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	-	0.6222	62.22%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	+	0.6631	66.31%
Acute Oral Toxicity (c)	III	0.4083	40.83%
Estrogen receptor binding	-	0.7022	70.22%
Androgen receptor binding	-	0.7907	79.07%
Thyroid receptor binding	-	0.8315	83.15%
Glucocorticoid receptor binding	-	0.7937	79.37%
Aromatase binding	-	0.8940	89.40%
PPAR gamma	-	0.8933	89.33%
Honey bee toxicity	-	0.8548	85.48%
Biodegradation	+	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6002	60.02%
Fish aquatic toxicity	-	0.5613	56.13%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.47%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.39%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.54%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.70%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.81%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	85.09%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.26%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.88%	95.56%

Plants that contains it

• Vigna angularis

Cross-Links

• PubChem: 101683182
• NPASS: NPC260481
• LOTUS: LTS0132718
• wikiData: Q75064748