Spiroleptosphol U

Details

• Internal ID: 60e1af8d-663a-4ff3-bc3f-2514c79e8b2d
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (1S,2R,5S,8R)-8-hydroxy-1-[(2R)-3-oxobutan-2-yl]-2-[(1E,3E)-penta-1,3-dienyl]-6-oxabicyclo[3.2.1]oct-3-en-7-one
• SMILES (Canonical): CC=CC=CC1C=CC2C(C1(C(=O)O2)C(C)C(=O)C)O
• SMILES (Isomeric): C/C=C/C=C/[C@@H]1C=C[C@H]2[C@@H]([C@@]1(C(=O)O2)[C@@H](C)C(=O)C)O
• InChI: InChI=1S/C16H20O4/c1-4-5-6-7-12-8-9-13-14(18)16(12,15(19)20-13)10(2)11(3)17/h4-10,12-14,18H,1-3H3/b5-4+,7-6+/t10-,12+,13-,14-,16+/m0/s1
• InChI Key: XUVKTFLRSCIJEP-VZMLLMINSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 276.33 g/mol
• Exact Mass: 276.13615911 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.80
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• (1S,2R,5S,8R)-8-hydroxy-1-[(2R)-3-oxobutan-2-yl]-2-[(1E,3E)-penta-1,3-dienyl]-6-oxabicyclo[3.2.1]oct-3-en-7-one
• (1S,2R,5S,8R)-8-hydroxy-1-((2R)-3-oxobutan-2-yl)-2-((1E,3E)-penta-1,3-dienyl)-6-oxabicyclo(3.2.1)oct-3-en-7-one
• RefChem:184883
• CHEBI:206221

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9479	94.79%
Caco-2	+	0.5593	55.93%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6352	63.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8548	85.48%
OATP1B3 inhibitior	+	0.9269	92.69%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6466	64.66%
P-glycoprotein inhibitior	-	0.8543	85.43%
P-glycoprotein substrate	-	0.7967	79.67%
CYP3A4 substrate	+	0.5382	53.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8870	88.70%
CYP3A4 inhibition	-	0.8371	83.71%
CYP2C9 inhibition	-	0.9792	97.92%
CYP2C19 inhibition	-	0.9624	96.24%
CYP2D6 inhibition	-	0.9725	97.25%
CYP1A2 inhibition	-	0.9386	93.86%
CYP2C8 inhibition	-	0.9509	95.09%
CYP inhibitory promiscuity	-	0.9666	96.66%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Non-required	0.4308	43.08%
Eye corrosion	-	0.9108	91.08%
Eye irritation	-	0.9616	96.16%
Skin irritation	-	0.5255	52.55%
Skin corrosion	-	0.8120	81.20%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4689	46.89%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	-	0.7372	73.72%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	+	0.5554	55.54%
Nephrotoxicity	-	0.5527	55.27%
Acute Oral Toxicity (c)	III	0.4830	48.30%
Estrogen receptor binding	+	0.5829	58.29%
Androgen receptor binding	-	0.5053	50.53%
Thyroid receptor binding	-	0.6633	66.33%
Glucocorticoid receptor binding	-	0.7988	79.88%
Aromatase binding	-	0.6928	69.28%
PPAR gamma	-	0.6415	64.15%
Honey bee toxicity	-	0.8400	84.00%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8784	87.84%

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	92.03%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.54%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.86%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.60%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.54%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.72%	91.11%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.37%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.46%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.22%	96.77%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 146682647
• LOTUS: LTS0273064
• wikiData: Q105342614