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

Details

• Internal ID: cfdc29e6-54f9-492b-b999-a965eb18a784
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (4S,5S)-5-[(3S,4R)-4-chloro-3-hydroxy-2-methyl-5-oxocyclopenten-1-yl]-3-methylidene-4-(3-oxobutyl)oxolan-2-one
• SMILES (Canonical): CC1=C(C(=O)C(C1O)Cl)C2C(C(=C)C(=O)O2)CCC(=O)C
• SMILES (Isomeric): CC1=C(C(=O)[C@@H]([C@H]1O)Cl)[C@@H]2[C@H](C(=C)C(=O)O2)CCC(=O)C
• InChI: InChI=1S/C15H17ClO5/c1-6(17)4-5-9-7(2)15(20)21-14(9)10-8(3)12(18)11(16)13(10)19/h9,11-12,14,18H,2,4-5H2,1,3H3/t9-,11+,12-,14-/m0/s1
• InChI Key: JWUMTWYVBGJABK-TWJQMWNJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₇ClO₅
• Molecular Weight: 312.74 g/mol
• Exact Mass: 312.0764513 g/mol
• Topological Polar Surface Area (TPSA): 80.70 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 1.32
• 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	+	0.9835	98.35%
Caco-2	+	0.5773	57.73%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6885	68.85%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.8758	87.58%
OATP1B3 inhibitior	+	0.8992	89.92%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9455	94.55%
P-glycoprotein inhibitior	-	0.8463	84.63%
P-glycoprotein substrate	-	0.8537	85.37%
CYP3A4 substrate	+	0.5349	53.49%
CYP2C9 substrate	-	0.7974	79.74%
CYP2D6 substrate	-	0.8938	89.38%
CYP3A4 inhibition	-	0.8791	87.91%
CYP2C9 inhibition	-	0.7829	78.29%
CYP2C19 inhibition	-	0.7509	75.09%
CYP2D6 inhibition	-	0.8886	88.86%
CYP1A2 inhibition	-	0.7507	75.07%
CYP2C8 inhibition	-	0.8506	85.06%
CYP inhibitory promiscuity	-	0.9038	90.38%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7841	78.41%
Carcinogenicity (trinary)	Non-required	0.4442	44.42%
Eye corrosion	-	0.9484	94.84%
Eye irritation	+	0.5309	53.09%
Skin irritation	-	0.6180	61.80%
Skin corrosion	-	0.8066	80.66%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7311	73.11%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.6880	68.80%
skin sensitisation	-	0.7744	77.44%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.5811	58.11%
Acute Oral Toxicity (c)	III	0.6248	62.48%
Estrogen receptor binding	-	0.4784	47.84%
Androgen receptor binding	-	0.5401	54.01%
Thyroid receptor binding	-	0.5731	57.31%
Glucocorticoid receptor binding	-	0.5564	55.64%
Aromatase binding	-	0.7622	76.22%
PPAR gamma	-	0.6901	69.01%
Honey bee toxicity	-	0.7670	76.70%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9864	98.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.69%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.47%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.34%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.95%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	85.65%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.74%	99.23%

Plants that contains it

• Achillea ligustica
• Anemonoides raddeana

Cross-Links

• PubChem: 12097070
• NPASS: NPC84252
• LOTUS: LTS0015109
• wikiData: Q105136374