(4R,5S)-5-(5-hydroxy-2-methyl-3-oxocyclopenten-1-yl)-3-methylidene-4-(3-oxobutyl)oxolan-2-one

Details

• Internal ID: 29dbf0bb-dbe3-4882-8dfd-ed1022c3cb67
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (4R,5S)-5-(5-hydroxy-2-methyl-3-oxocyclopenten-1-yl)-3-methylidene-4-(3-oxobutyl)oxolan-2-one
• SMILES (Canonical): CC1=C(C(CC1=O)O)C2C(C(=C)C(=O)O2)CCC(=O)C
• SMILES (Isomeric): CC1=C(C(CC1=O)O)[C@@H]2[C@@H](C(=C)C(=O)O2)CCC(=O)C
• InChI: InChI=1S/C15H18O5/c1-7(16)4-5-10-8(2)15(19)20-14(10)13-9(3)11(17)6-12(13)18/h10,12,14,18H,2,4-6H2,1,3H3/t10-,12?,14+/m1/s1
• InChI Key: AOWOLSRNDJUAJJ-HDDSUISISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 80.70 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 1.10
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9762	97.62%
Caco-2	+	0.7592	75.92%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6779	67.79%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.8840	88.40%
OATP1B3 inhibitior	+	0.9013	90.13%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9124	91.24%
P-glycoprotein inhibitior	-	0.7926	79.26%
P-glycoprotein substrate	-	0.8608	86.08%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.7970	79.70%
CYP2D6 substrate	-	0.8970	89.70%
CYP3A4 inhibition	-	0.8228	82.28%
CYP2C9 inhibition	-	0.8959	89.59%
CYP2C19 inhibition	-	0.8708	87.08%
CYP2D6 inhibition	-	0.9366	93.66%
CYP1A2 inhibition	-	0.7372	73.72%
CYP2C8 inhibition	-	0.9024	90.24%
CYP inhibitory promiscuity	-	0.9403	94.03%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8928	89.28%
Carcinogenicity (trinary)	Non-required	0.6380	63.80%
Eye corrosion	-	0.9567	95.67%
Eye irritation	+	0.7450	74.50%
Skin irritation	+	0.5630	56.30%
Skin corrosion	-	0.8183	81.83%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7011	70.11%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.7584	75.84%
skin sensitisation	-	0.7658	76.58%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.6065	60.65%
Acute Oral Toxicity (c)	III	0.5996	59.96%
Estrogen receptor binding	-	0.5262	52.62%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5915	59.15%
Glucocorticoid receptor binding	+	0.6012	60.12%
Aromatase binding	-	0.7832	78.32%
PPAR gamma	-	0.5526	55.26%
Honey bee toxicity	-	0.8437	84.37%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9451	94.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.95%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.36%	99.23%
CHEMBL2581	P07339	Cathepsin D	88.75%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.28%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.20%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.81%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.79%	93.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.59%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.60%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	80.19%	94.73%

Plants that contains it

• Artemisia anomala
• Tanacetum macrophyllum

Cross-Links

• PubChem: 102226845
• LOTUS: LTS0000321
• wikiData: Q104915995