(5S)-5-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-methoxy-4-methylfuran-2-one

Details

• Internal ID: a02d798f-5b92-4748-b4c2-db07b57dfa23
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (5S)-5-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-methoxy-4-methylfuran-2-one
• SMILES (Canonical): CC1=CC(=O)OC1(CC=C(C)CCC=C(C)C)OC
• SMILES (Isomeric): CC1=CC(=O)O[C@]1(C/C=C(\C)/CCC=C(C)C)OC
• InChI: InChI=1S/C16H24O3/c1-12(2)7-6-8-13(3)9-10-16(18-5)14(4)11-15(17)19-16/h7,9,11H,6,8,10H2,1-5H3/b13-9+/t16-/m0/s1
• InChI Key: LCMSHPJWLCITEF-WQMJKPAKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₃
• Molecular Weight: 264.36 g/mol
• Exact Mass: 264.17254462 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.92
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9811	98.11%
Caco-2	+	0.9056	90.56%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7211	72.11%
OATP2B1 inhibitior	-	0.8571	85.71%
OATP1B1 inhibitior	+	0.8747	87.47%
OATP1B3 inhibitior	+	0.9115	91.15%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	+	0.6262	62.62%
P-glycoprotein inhibitior	-	0.8595	85.95%
P-glycoprotein substrate	-	0.9026	90.26%
CYP3A4 substrate	+	0.5373	53.73%
CYP2C9 substrate	+	0.5989	59.89%
CYP2D6 substrate	-	0.8984	89.84%
CYP3A4 inhibition	-	0.7969	79.69%
CYP2C9 inhibition	-	0.8045	80.45%
CYP2C19 inhibition	-	0.6291	62.91%
CYP2D6 inhibition	-	0.9459	94.59%
CYP1A2 inhibition	-	0.6810	68.10%
CYP2C8 inhibition	-	0.8273	82.73%
CYP inhibitory promiscuity	-	0.7677	76.77%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8928	89.28%
Carcinogenicity (trinary)	Non-required	0.6172	61.72%
Eye corrosion	-	0.9463	94.63%
Eye irritation	-	0.7057	70.57%
Skin irritation	-	0.5583	55.83%
Skin corrosion	-	0.9699	96.99%
Ames mutagenesis	-	0.6924	69.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.5603	56.03%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5438	54.38%
skin sensitisation	-	0.6969	69.69%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	-	0.7889	78.89%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	+	0.7528	75.28%
Acute Oral Toxicity (c)	III	0.4834	48.34%
Estrogen receptor binding	-	0.6258	62.58%
Androgen receptor binding	-	0.5997	59.97%
Thyroid receptor binding	-	0.5956	59.56%
Glucocorticoid receptor binding	+	0.7028	70.28%
Aromatase binding	+	0.5667	56.67%
PPAR gamma	+	0.7658	76.58%
Honey bee toxicity	-	0.8379	83.79%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9668	96.68%

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	96.83%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	94.33%	94.73%
CHEMBL2581	P07339	Cathepsin D	93.50%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.36%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.34%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.98%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.87%	96.09%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	81.75%	92.08%

Plants that contains it

• Daphnopsis macrophylla

Cross-Links

• PubChem: 162907369
• LOTUS: LTS0035036
• wikiData: Q105149898