[(1S,3S,7R,7aS)-4-(acetyloxymethyl)-7-(hydroxymethyl)-3,7-dimethoxy-3,7a-dihydro-1H-cyclopenta[c]pyran-1-yl] 3-methylbutanoate

Details

• Internal ID: 03ce43e2-7850-4706-9b6c-a31232f2eaaa
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters
• IUPAC Name: [(1S,3S,7R,7aS)-4-(acetyloxymethyl)-7-(hydroxymethyl)-3,7-dimethoxy-3,7a-dihydro-1H-cyclopenta[c]pyran-1-yl] 3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OC1C2C(=C(C(O1)OC)COC(=O)C)C=CC2(CO)OC
• SMILES (Isomeric): CC(C)CC(=O)O[C@H]1[C@H]2C(=C([C@H](O1)OC)COC(=O)C)C=C[C@@]2(CO)OC
• InChI: InChI=1S/C19H28O8/c1-11(2)8-15(22)26-18-16-13(6-7-19(16,10-20)24-5)14(9-25-12(3)21)17(23-4)27-18/h6-7,11,16-18,20H,8-10H2,1-5H3/t16-,17+,18-,19+/m1/s1
• InChI Key: PCWLZMIAWSKQEO-HCXYKTFWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₈O₈
• Molecular Weight: 384.40 g/mol
• Exact Mass: 384.17841785 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 1.33
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9570	95.70%
Caco-2	+	0.5571	55.71%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7475	74.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8796	87.96%
OATP1B3 inhibitior	+	0.8892	88.92%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5436	54.36%
P-glycoprotein inhibitior	-	0.4601	46.01%
P-glycoprotein substrate	-	0.5122	51.22%
CYP3A4 substrate	+	0.6292	62.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8841	88.41%
CYP3A4 inhibition	-	0.8114	81.14%
CYP2C9 inhibition	-	0.8619	86.19%
CYP2C19 inhibition	-	0.8566	85.66%
CYP2D6 inhibition	-	0.9469	94.69%
CYP1A2 inhibition	-	0.7931	79.31%
CYP2C8 inhibition	-	0.5618	56.18%
CYP inhibitory promiscuity	-	0.9236	92.36%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5780	57.80%
Eye corrosion	-	0.9822	98.22%
Eye irritation	-	0.9340	93.40%
Skin irritation	-	0.6874	68.74%
Skin corrosion	-	0.9360	93.60%
Ames mutagenesis	+	0.5463	54.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.4810	48.10%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.6218	62.18%
skin sensitisation	-	0.7673	76.73%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.6244	62.44%
Acute Oral Toxicity (c)	III	0.5822	58.22%
Estrogen receptor binding	+	0.5663	56.63%
Androgen receptor binding	+	0.6334	63.34%
Thyroid receptor binding	+	0.5972	59.72%
Glucocorticoid receptor binding	+	0.8304	83.04%
Aromatase binding	+	0.5179	51.79%
PPAR gamma	+	0.5712	57.12%
Honey bee toxicity	-	0.7562	75.62%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.7659	76.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.93%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.79%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.34%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.43%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	87.40%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.16%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.81%	96.00%
CHEMBL2581	P07339	Cathepsin D	83.49%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.89%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.15%	89.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.03%	97.28%

Plants that contains it

• Valeriana jatamansi

Cross-Links

• PubChem: 57337414
• LOTUS: LTS0038020
• wikiData: Q105206110