(3R,5R)-3,5-dihydroxy-1-[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrrolidin-2-one

Details

• Internal ID: 35513c7c-eaf3-4f3c-937f-1686235e99ec
• Taxonomy: Organoheterocyclic compounds > Pyrrolidines > N-alkylpyrrolidines
• IUPAC Name: (3R,5R)-3,5-dihydroxy-1-[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrrolidin-2-one
• SMILES (Canonical): C1C=C(C(O1)N2C(CC(C2=O)O)O)CO
• SMILES (Isomeric): C1C=C(C(O1)N2[C@@H](C[C@H](C2=O)O)O)CO
• InChI: InChI=1S/C9H13NO5/c11-4-5-1-2-15-9(5)10-7(13)3-6(12)8(10)14/h1,6-7,9,11-13H,2-4H2/t6-,7-,9?/m1/s1
• InChI Key: UQDNRNARHGVYKC-UMPGHQJDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₃NO₅
• Molecular Weight: 215.20 g/mol
• Exact Mass: 215.07937252 g/mol
• Topological Polar Surface Area (TPSA): 90.20 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -1.83
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8776	87.76%
Caco-2	-	0.5638	56.38%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5085	50.85%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.9223	92.23%
OATP1B3 inhibitior	+	0.9386	93.86%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9170	91.70%
P-glycoprotein inhibitior	-	0.9766	97.66%
P-glycoprotein substrate	-	0.9205	92.05%
CYP3A4 substrate	-	0.5161	51.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8405	84.05%
CYP3A4 inhibition	-	0.9923	99.23%
CYP2C9 inhibition	-	0.8630	86.30%
CYP2C19 inhibition	-	0.8932	89.32%
CYP2D6 inhibition	-	0.9412	94.12%
CYP1A2 inhibition	-	0.8739	87.39%
CYP2C8 inhibition	-	0.9490	94.90%
CYP inhibitory promiscuity	-	0.9659	96.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5426	54.26%
Eye corrosion	-	0.9797	97.97%
Eye irritation	+	0.7130	71.30%
Skin irritation	-	0.7389	73.89%
Skin corrosion	-	0.9035	90.35%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8534	85.34%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	+	0.6928	69.28%
skin sensitisation	-	0.8707	87.07%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5120	51.20%
Estrogen receptor binding	-	0.7347	73.47%
Androgen receptor binding	+	0.5347	53.47%
Thyroid receptor binding	-	0.5900	59.00%
Glucocorticoid receptor binding	-	0.4715	47.15%
Aromatase binding	-	0.8555	85.55%
PPAR gamma	-	0.7091	70.91%
Honey bee toxicity	-	0.8837	88.37%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	-	0.7877	78.77%

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	93.61%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.32%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.80%	97.09%
CHEMBL1978	P11511	Cytochrome P450 19A1	87.28%	91.76%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.55%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.66%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.31%	89.00%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	80.48%	98.46%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.29%	94.45%

Plants that contains it

• Hemerocallis fulva

Cross-Links

• PubChem: 14779023
• LOTUS: LTS0065539
• wikiData: Q104402901