(3R,4R,5S)-5-[(1S,2S)-2-hydroxy-2-methyl-5-oxocyclopent-3-en-1-yl]-3-methyl-4-(3-oxobutyl)oxolan-2-one

Details

• Internal ID: 2bac5c68-e6de-40fe-9da4-a6d8819be6ae
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3R,4R,5S)-5-[(1S,2S)-2-hydroxy-2-methyl-5-oxocyclopent-3-en-1-yl]-3-methyl-4-(3-oxobutyl)oxolan-2-one
• SMILES (Canonical): CC1C(C(OC1=O)C2C(=O)C=CC2(C)O)CCC(=O)C
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H](OC1=O)[C@@H]2C(=O)C=C[C@]2(C)O)CCC(=O)C
• InChI: InChI=1S/C15H20O5/c1-8(16)4-5-10-9(2)14(18)20-13(10)12-11(17)6-7-15(12,3)19/h6-7,9-10,12-13,19H,4-5H2,1-3H3/t9-,10-,12+,13+,15+/m1/s1
• InChI Key: GYUDBKZPWJSHBH-RPCGMBGBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 80.70 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 1.04
• 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	+	0.9627	96.27%
Caco-2	+	0.5280	52.80%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7226	72.26%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.8679	86.79%
OATP1B3 inhibitior	+	0.8939	89.39%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9243	92.43%
P-glycoprotein inhibitior	-	0.8660	86.60%
P-glycoprotein substrate	-	0.7696	76.96%
CYP3A4 substrate	+	0.5609	56.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9004	90.04%
CYP3A4 inhibition	-	0.8181	81.81%
CYP2C9 inhibition	-	0.9003	90.03%
CYP2C19 inhibition	-	0.9389	93.89%
CYP2D6 inhibition	-	0.9610	96.10%
CYP1A2 inhibition	-	0.8310	83.10%
CYP2C8 inhibition	-	0.9003	90.03%
CYP inhibitory promiscuity	-	0.9644	96.44%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8928	89.28%
Carcinogenicity (trinary)	Non-required	0.5923	59.23%
Eye corrosion	-	0.9591	95.91%
Eye irritation	-	0.9352	93.52%
Skin irritation	+	0.5888	58.88%
Skin corrosion	-	0.6942	69.42%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4893	48.93%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.5357	53.57%
skin sensitisation	-	0.7619	76.19%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	-	0.7333	73.33%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.5723	57.23%
Acute Oral Toxicity (c)	III	0.6350	63.50%
Estrogen receptor binding	+	0.5979	59.79%
Androgen receptor binding	+	0.5316	53.16%
Thyroid receptor binding	-	0.5336	53.36%
Glucocorticoid receptor binding	-	0.4888	48.88%
Aromatase binding	-	0.7447	74.47%
PPAR gamma	-	0.6618	66.18%
Honey bee toxicity	-	0.8675	86.75%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.8764	87.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.32%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.41%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.26%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.62%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.84%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.78%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.73%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.32%	94.45%

Plants that contains it

• Tanacetum parthenium

Cross-Links

• PubChem: 162842016
• LOTUS: LTS0266618
• wikiData: Q105024175