(3R,4S,5S)-4-hydroxy-3-[(1E,4E)-4-methyl-7-(5-oxo-2H-furan-3-yl)hepta-1,4-dienyl]-5-(2-methylprop-1-enyl)tetrahydrofuran-2-one

Details

• Internal ID: 5feb7132-45e1-4215-8ace-56eb64f47a19
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3R,4S,5S)-4-hydroxy-3-[(1E,4E)-4-methyl-7-(5-oxo-2H-furan-3-yl)hepta-1,4-dienyl]-5-(2-methylprop-1-enyl)oxolan-2-one
• InChI: InChI=1S/C20H26O5/c1-13(2)10-17-19(22)16(20(23)25-17)9-5-7-14(3)6-4-8-15-11-18(21)24-12-15/h5-6,9-11,16-17,19,22H,4,7-8,12H2,1-3H3/b9-5+,14-6+/t16-,17+,19+/m1/s1
• InChI Key: GLONEOMMWYZBSN-UWLXZJRSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₅
• Molecular Weight: 346.40 g/mol
• Exact Mass: 346.17802393 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.01
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• CHEMBL1086787
• SCHEMBL14945633
• (3R,4S,5S)-4-hydroxy-3-[(1E,4E)-4-methyl-7-(5-oxo-2H-furan-3-yl)hepta-1,4-dienyl]-5-(2-methylprop-1-enyl)tetrahydrofuran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9599	95.99%
Caco-2	-	0.5646	56.46%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8040	80.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8987	89.87%
OATP1B3 inhibitior	+	0.9228	92.28%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.6999	69.99%
P-glycoprotein inhibitior	-	0.5931	59.31%
P-glycoprotein substrate	-	0.6159	61.59%
CYP3A4 substrate	+	0.6149	61.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8996	89.96%
CYP3A4 inhibition	-	0.6858	68.58%
CYP2C9 inhibition	-	0.6675	66.75%
CYP2C19 inhibition	-	0.8034	80.34%
CYP2D6 inhibition	-	0.8682	86.82%
CYP1A2 inhibition	-	0.5893	58.93%
CYP2C8 inhibition	-	0.8055	80.55%
CYP inhibitory promiscuity	-	0.9373	93.73%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8928	89.28%
Carcinogenicity (trinary)	Non-required	0.5762	57.62%
Eye corrosion	-	0.9734	97.34%
Eye irritation	-	0.9493	94.93%
Skin irritation	-	0.5236	52.36%
Skin corrosion	-	0.9487	94.87%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6538	65.38%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8321	83.21%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.5991	59.91%
Acute Oral Toxicity (c)	III	0.7034	70.34%
Estrogen receptor binding	-	0.5788	57.88%
Androgen receptor binding	-	0.5961	59.61%
Thyroid receptor binding	-	0.6300	63.00%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.6384	63.84%
PPAR gamma	+	0.6477	64.77%
Honey bee toxicity	-	0.7192	71.92%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9858	98.58%

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	95.61%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.72%	89.00%
CHEMBL2581	P07339	Cathepsin D	90.43%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.11%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.19%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.69%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.99%	85.14%
CHEMBL1937	Q92769	Histone deacetylase 2	83.51%	94.75%
CHEMBL3401	O75469	Pregnane X receptor	83.13%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.46%	97.25%

Plants that contains it

• Heteroplexis microcephala

Cross-Links

• PubChem: 44179792
• LOTUS: LTS0224179
• wikiData: Q105011129