(2S)-4-acetyl-2-[(E,5S)-5-hydroxyhex-1-enyl]-5-methoxy-2-methylfuran-3-one

Details

• Internal ID: 605e98d2-74a5-4ca3-98de-6f55a284e521
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty alcohols
• IUPAC Name: (2S)-4-acetyl-2-[(E,5S)-5-hydroxyhex-1-enyl]-5-methoxy-2-methylfuran-3-one
• SMILES (Canonical): CC(CCC=CC1(C(=O)C(=C(O1)OC)C(=O)C)C)O
• SMILES (Isomeric): C[C@@H](CC/C=C/[C@]1(C(=O)C(=C(O1)OC)C(=O)C)C)O
• InChI: InChI=1S/C14H20O5/c1-9(15)7-5-6-8-14(3)12(17)11(10(2)16)13(18-4)19-14/h6,8-9,15H,5,7H2,1-4H3/b8-6+/t9-,14-/m0/s1
• InChI Key: CFANDGBDJFIBOZ-LAQTXOASSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₀O₅
• Molecular Weight: 268.30 g/mol
• Exact Mass: 268.13107373 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.51
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9676	96.76%
Caco-2	-	0.5555	55.55%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6357	63.57%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.8680	86.80%
OATP1B3 inhibitior	+	0.9038	90.38%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7521	75.21%
BSEP inhibitior	-	0.6206	62.06%
P-glycoprotein inhibitior	-	0.9276	92.76%
P-glycoprotein substrate	-	0.8395	83.95%
CYP3A4 substrate	+	0.5666	56.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8343	83.43%
CYP3A4 inhibition	-	0.7181	71.81%
CYP2C9 inhibition	-	0.8342	83.42%
CYP2C19 inhibition	-	0.8311	83.11%
CYP2D6 inhibition	-	0.9446	94.46%
CYP1A2 inhibition	-	0.7797	77.97%
CYP2C8 inhibition	-	0.9325	93.25%
CYP inhibitory promiscuity	-	0.9469	94.69%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8928	89.28%
Carcinogenicity (trinary)	Non-required	0.5689	56.89%
Eye corrosion	-	0.9778	97.78%
Eye irritation	-	0.9453	94.53%
Skin irritation	-	0.5461	54.61%
Skin corrosion	-	0.8995	89.95%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5430	54.30%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5091	50.91%
skin sensitisation	-	0.8089	80.89%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.6263	62.63%
Acute Oral Toxicity (c)	III	0.4591	45.91%
Estrogen receptor binding	+	0.5344	53.44%
Androgen receptor binding	-	0.7733	77.33%
Thyroid receptor binding	-	0.6235	62.35%
Glucocorticoid receptor binding	+	0.5762	57.62%
Aromatase binding	+	0.6170	61.70%
PPAR gamma	+	0.5688	56.88%
Honey bee toxicity	-	0.8005	80.05%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.7734	77.34%

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	95.71%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.01%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.87%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.89%	94.45%
CHEMBL2581	P07339	Cathepsin D	85.41%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	84.58%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.01%	99.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.13%	96.77%
CHEMBL340	P08684	Cytochrome P450 3A4	82.56%	91.19%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.18%	96.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.53%	94.33%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.38%	95.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.00%	95.50%

Plants that contains it

• Huperzia serrata

Cross-Links

• PubChem: 163186078
• LOTUS: LTS0092292
• wikiData: Q104956268