Topsentolide A2

Details

• Internal ID: a6be1351-dc46-48bf-b719-cbb04b99aa7a
• Taxonomy: Organoheterocyclic compounds > Lactones
• IUPAC Name: (2S,4Z)-2-[(E)-2-[(2R,3S)-3-[(2Z,5Z)-octa-2,5-dienyl]oxiran-2-yl]ethenyl]-3,6,7,8-tetrahydro-2H-oxonin-9-one
• SMILES (Canonical): CCC=CCC=CCC1C(O1)C=CC2CC=CCCCC(=O)O2
• SMILES (Isomeric): CC/C=C\C/C=C\C[C@H]1[C@H](O1)/C=C/[C@@H]2C/C=C\CCCC(=O)O2
• InChI: InChI=1S/C20H28O3/c1-2-3-4-5-6-10-13-18-19(23-18)16-15-17-12-9-7-8-11-14-20(21)22-17/h3-4,6-7,9-10,15-19H,2,5,8,11-14H2,1H3/b4-3-,9-7-,10-6-,16-15+/t17-,18-,19+/m0/s1
• InChI Key: VZWNYWSEUACDLE-VYXNFCKLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 38.80 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.65
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 7

Synonyms

• CHEMBL479885

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9937	99.37%
Caco-2	-	0.5276	52.76%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5343	53.43%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	+	0.8244	82.44%
OATP1B3 inhibitior	+	0.9599	95.99%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6995	69.95%
P-glycoprotein inhibitior	-	0.5505	55.05%
P-glycoprotein substrate	-	0.7933	79.33%
CYP3A4 substrate	+	0.5588	55.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8659	86.59%
CYP3A4 inhibition	-	0.8861	88.61%
CYP2C9 inhibition	-	0.8507	85.07%
CYP2C19 inhibition	-	0.7439	74.39%
CYP2D6 inhibition	-	0.9332	93.32%
CYP1A2 inhibition	-	0.6934	69.34%
CYP2C8 inhibition	-	0.8104	81.04%
CYP inhibitory promiscuity	-	0.8543	85.43%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6021	60.21%
Eye corrosion	-	0.8375	83.75%
Eye irritation	-	0.7530	75.30%
Skin irritation	-	0.6500	65.00%
Skin corrosion	-	0.9068	90.68%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7315	73.15%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.6678	66.78%
skin sensitisation	+	0.5447	54.47%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	-	0.7444	74.44%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	-	0.7369	73.69%
Acute Oral Toxicity (c)	III	0.7779	77.79%
Estrogen receptor binding	+	0.7378	73.78%
Androgen receptor binding	-	0.8058	80.58%
Thyroid receptor binding	-	0.6589	65.89%
Glucocorticoid receptor binding	+	0.5786	57.86%
Aromatase binding	+	0.6273	62.73%
PPAR gamma	+	0.5468	54.68%
Honey bee toxicity	-	0.8841	88.41%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.8460	84.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	93.53%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.04%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.44%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.54%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.99%	96.77%
CHEMBL3401	O75469	Pregnane X receptor	85.79%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.82%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.10%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.09%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.09%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.90%	100.00%
CHEMBL4208	P20618	Proteasome component C5	80.27%	90.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11602133
• LOTUS: LTS0129966
• wikiData: Q105300024