methyl (1S,5S)-5-[(2S)-3-hydroxy-1-methoxy-1-oxopropan-2-yl]-2-(hydroxymethyl)cyclopent-2-ene-1-carboxylate

Details

• Internal ID: 6aa9010b-4bd7-4a90-a395-27dedb91df99
• Taxonomy: Organic acids and derivatives > Hydroxy acids and derivatives > Beta hydroxy acids and derivatives
• IUPAC Name: methyl (1S,5S)-5-[(2S)-3-hydroxy-1-methoxy-1-oxopropan-2-yl]-2-(hydroxymethyl)cyclopent-2-ene-1-carboxylate
• SMILES (Canonical): COC(=O)C1C(CC=C1CO)C(CO)C(=O)OC
• SMILES (Isomeric): COC(=O)[C@H]1[C@H](CC=C1CO)[C@@H](CO)C(=O)OC
• InChI: InChI=1S/C12H18O6/c1-17-11(15)9(6-14)8-4-3-7(5-13)10(8)12(16)18-2/h3,8-10,13-14H,4-6H2,1-2H3/t8-,9-,10-/m1/s1
• InChI Key: SDWHLKFQMBNHOO-OPRDCNLKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₈O₆
• Molecular Weight: 258.27 g/mol
• Exact Mass: 258.11033829 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -0.50
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8246	82.46%
Caco-2	-	0.5441	54.41%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8158	81.58%
OATP2B1 inhibitior	-	0.8516	85.16%
OATP1B1 inhibitior	+	0.9468	94.68%
OATP1B3 inhibitior	+	0.9493	94.93%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9643	96.43%
P-glycoprotein inhibitior	-	0.9384	93.84%
P-glycoprotein substrate	-	0.7443	74.43%
CYP3A4 substrate	+	0.5163	51.63%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8513	85.13%
CYP3A4 inhibition	-	0.8739	87.39%
CYP2C9 inhibition	-	0.8347	83.47%
CYP2C19 inhibition	-	0.8001	80.01%
CYP2D6 inhibition	-	0.8870	88.70%
CYP1A2 inhibition	-	0.8028	80.28%
CYP2C8 inhibition	-	0.9224	92.24%
CYP inhibitory promiscuity	-	0.8222	82.22%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.6993	69.93%
Carcinogenicity (trinary)	Non-required	0.7092	70.92%
Eye corrosion	-	0.9338	93.38%
Eye irritation	-	0.8598	85.98%
Skin irritation	-	0.7078	70.78%
Skin corrosion	-	0.9629	96.29%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7444	74.44%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.5178	51.78%
skin sensitisation	-	0.7259	72.59%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	+	0.6090	60.90%
Acute Oral Toxicity (c)	III	0.6055	60.55%
Estrogen receptor binding	-	0.6294	62.94%
Androgen receptor binding	+	0.7451	74.51%
Thyroid receptor binding	-	0.6867	68.67%
Glucocorticoid receptor binding	-	0.5264	52.64%
Aromatase binding	-	0.8415	84.15%
PPAR gamma	-	0.7313	73.13%
Honey bee toxicity	-	0.8831	88.31%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9700	97.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.42%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.64%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.08%	94.45%
CHEMBL2581	P07339	Cathepsin D	87.38%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.10%	97.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.27%	91.24%
CHEMBL340	P08684	Cytochrome P450 3A4	83.65%	91.19%

Plants that contains it

• Gardenia jasminoides

Cross-Links

• PubChem: 163048430
• LOTUS: LTS0028252
• wikiData: Q105250894