(5S,9S)-2-[(2S)-butan-2-yl]-9-ethenyl-9-methyl-1,7-dioxaspiro[4.4]non-2-ene-4,6-dione

Details

• Internal ID: add71b08-c407-407c-875a-a63bae9924af
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (5S,9S)-2-[(2S)-butan-2-yl]-9-ethenyl-9-methyl-1,7-dioxaspiro[4.4]non-2-ene-4,6-dione
• SMILES (Canonical): CCC(C)C1=CC(=O)C2(O1)C(=O)OCC2(C)C=C
• SMILES (Isomeric): CC[C@H](C)C1=CC(=O)[C@]2(O1)C(=O)OC[C@]2(C)C=C
• InChI: InChI=1S/C14H18O4/c1-5-9(3)10-7-11(15)14(18-10)12(16)17-8-13(14,4)6-2/h6-7,9H,2,5,8H2,1,3-4H3/t9-,13-,14-/m0/s1
• InChI Key: QQXSQPKEGWRLPS-HERUPUMHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.29 g/mol
• Exact Mass: 250.12050905 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.00
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9815	98.15%
Caco-2	+	0.8064	80.64%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5507	55.07%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.8724	87.24%
OATP1B3 inhibitior	+	0.9199	91.99%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8085	80.85%
P-glycoprotein inhibitior	-	0.9258	92.58%
P-glycoprotein substrate	-	0.8136	81.36%
CYP3A4 substrate	-	0.5329	53.29%
CYP2C9 substrate	-	0.8185	81.85%
CYP2D6 substrate	-	0.8979	89.79%
CYP3A4 inhibition	-	0.6545	65.45%
CYP2C9 inhibition	-	0.8100	81.00%
CYP2C19 inhibition	-	0.7853	78.53%
CYP2D6 inhibition	-	0.9333	93.33%
CYP1A2 inhibition	-	0.7519	75.19%
CYP2C8 inhibition	-	0.8228	82.28%
CYP inhibitory promiscuity	-	0.8572	85.72%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8743	87.43%
Carcinogenicity (trinary)	Non-required	0.4871	48.71%
Eye corrosion	-	0.9216	92.16%
Eye irritation	-	0.6150	61.50%
Skin irritation	-	0.6224	62.24%
Skin corrosion	-	0.9077	90.77%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6770	67.70%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.5709	57.09%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.7953	79.53%
Acute Oral Toxicity (c)	III	0.6454	64.54%
Estrogen receptor binding	-	0.5638	56.38%
Androgen receptor binding	+	0.6478	64.78%
Thyroid receptor binding	-	0.6376	63.76%
Glucocorticoid receptor binding	-	0.6896	68.96%
Aromatase binding	-	0.6213	62.13%
PPAR gamma	-	0.7465	74.65%
Honey bee toxicity	-	0.8999	89.99%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9465	94.65%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.14%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.16%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.54%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.87%	95.56%
CHEMBL230	P35354	Cyclooxygenase-2	89.60%	89.63%
CHEMBL3401	O75469	Pregnane X receptor	87.43%	94.73%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.09%	96.77%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	84.79%	85.30%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.94%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.86%	85.14%

Plants that contains it

• Cratoxylum cochinchinense
• Hypericum monogynum

Cross-Links

• PubChem: 10848289
• LOTUS: LTS0254682
• wikiData: Q105226129