methyl (1S,4aS,7S,7aR)-4'-ethyl-1-hydroxy-5'-oxospiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate

Details

• Internal ID: f7375abb-7bf7-4cf8-86fc-476adc0228ec
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: methyl (1S,4aS,7S,7aR)-4'-ethyl-1-hydroxy-5'-oxospiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
• SMILES (Canonical): CCC1=CC2(C=CC3C2C(OC=C3C(=O)OC)O)OC1=O
• SMILES (Isomeric): CCC1=C[C@]2(C=C[C@H]3[C@H]2[C@H](OC=C3C(=O)OC)O)OC1=O
• InChI: InChI=1S/C15H16O6/c1-3-8-6-15(21-12(8)16)5-4-9-10(13(17)19-2)7-20-14(18)11(9)15/h4-7,9,11,14,18H,3H2,1-2H3/t9-,11+,14+,15+/m1/s1
• InChI Key: IPOOVYQKBQYNQY-GQANPOSXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₆
• Molecular Weight: 292.28 g/mol
• Exact Mass: 292.09468823 g/mol
• Topological Polar Surface Area (TPSA): 82.10 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.83
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9797	97.97%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7204	72.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8342	83.42%
OATP1B3 inhibitior	+	0.9212	92.12%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6097	60.97%
P-glycoprotein inhibitior	-	0.8646	86.46%
P-glycoprotein substrate	-	0.7197	71.97%
CYP3A4 substrate	+	0.6174	61.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8691	86.91%
CYP3A4 inhibition	-	0.6450	64.50%
CYP2C9 inhibition	-	0.7998	79.98%
CYP2C19 inhibition	-	0.7835	78.35%
CYP2D6 inhibition	-	0.9329	93.29%
CYP1A2 inhibition	-	0.8494	84.94%
CYP2C8 inhibition	+	0.4570	45.70%
CYP inhibitory promiscuity	-	0.6813	68.13%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9525	95.25%
Carcinogenicity (trinary)	Danger	0.4422	44.22%
Eye corrosion	-	0.9570	95.70%
Eye irritation	-	0.9281	92.81%
Skin irritation	-	0.6218	62.18%
Skin corrosion	-	0.9032	90.32%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6828	68.28%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.5267	52.67%
skin sensitisation	-	0.6889	68.89%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.7385	73.85%
Acute Oral Toxicity (c)	III	0.5243	52.43%
Estrogen receptor binding	+	0.7600	76.00%
Androgen receptor binding	-	0.4926	49.26%
Thyroid receptor binding	-	0.5258	52.58%
Glucocorticoid receptor binding	-	0.5655	56.55%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.6509	65.09%
Honey bee toxicity	-	0.8943	89.43%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.8254	82.54%

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	97.22%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.13%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.59%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	91.96%	90.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.17%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.64%	86.33%
CHEMBL4208	P20618	Proteasome component C5	84.61%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.42%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	83.42%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.76%	95.56%
CHEMBL5028	O14672	ADAM10	81.48%	97.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.43%	92.62%

Plants that contains it

• Allamanda cathartica

Cross-Links

• PubChem: 163046287
• LOTUS: LTS0005397
• wikiData: Q105117379