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

Details

• Internal ID: 766dd214-11d5-463b-ab6b-7be0627204a2
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (4R,5S)-5-[(1S,2S)-2-hydroxy-2-methyl-5-oxocyclopent-3-en-1-yl]-4-[(1S)-1-hydroxy-3-oxobutyl]-3-methylideneoxolan-2-one
• SMILES (Canonical): CC(=O)CC(C1C(OC(=O)C1=C)C2C(=O)C=CC2(C)O)O
• SMILES (Isomeric): CC(=O)C[C@@H]([C@@H]1[C@H](OC(=O)C1=C)[C@@H]2C(=O)C=C[C@]2(C)O)O
• InChI: InChI=1S/C15H18O6/c1-7(16)6-10(18)11-8(2)14(19)21-13(11)12-9(17)4-5-15(12,3)20/h4-5,10-13,18,20H,2,6H2,1,3H3/t10-,11+,12-,13-,15-/m0/s1
• InChI Key: YDWPOGNXQRGSLE-KBRXKUPHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₆
• Molecular Weight: 294.30 g/mol
• Exact Mass: 294.11033829 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -0.07
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9602	96.02%
Caco-2	-	0.5966	59.66%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7059	70.59%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8898	88.98%
OATP1B3 inhibitior	+	0.9224	92.24%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9896	98.96%
P-glycoprotein inhibitior	-	0.8543	85.43%
P-glycoprotein substrate	-	0.7692	76.92%
CYP3A4 substrate	+	0.5649	56.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8970	89.70%
CYP3A4 inhibition	-	0.9388	93.88%
CYP2C9 inhibition	-	0.8776	87.76%
CYP2C19 inhibition	-	0.8557	85.57%
CYP2D6 inhibition	-	0.9505	95.05%
CYP1A2 inhibition	-	0.9182	91.82%
CYP2C8 inhibition	-	0.8706	87.06%
CYP inhibitory promiscuity	-	0.9277	92.77%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8428	84.28%
Carcinogenicity (trinary)	Non-required	0.4933	49.33%
Eye corrosion	-	0.9533	95.33%
Eye irritation	-	0.8491	84.91%
Skin irritation	-	0.5825	58.25%
Skin corrosion	-	0.8205	82.05%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5517	55.17%
Micronuclear	-	0.5441	54.41%
Hepatotoxicity	+	0.7483	74.83%
skin sensitisation	-	0.6012	60.12%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6168	61.68%
Acute Oral Toxicity (c)	III	0.5760	57.60%
Estrogen receptor binding	+	0.5885	58.85%
Androgen receptor binding	+	0.5579	55.79%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6273	62.73%
Aromatase binding	-	0.6253	62.53%
PPAR gamma	-	0.5897	58.97%
Honey bee toxicity	-	0.8386	83.86%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9260	92.60%

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	97.32%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.53%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.70%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.36%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.95%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.66%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.37%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.55%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	84.99%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.04%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.10%	99.23%

Plants that contains it

• Artemisia ludoviciana

Cross-Links

• PubChem: 14829065
• LOTUS: LTS0169762
• wikiData: Q105347076