(3S,4R,5R)-4-(Hydroxymethyl)-3,5-dimethyltetrahydrofuran-2-one

Details

• Internal ID: 34b6a394-8635-4afb-ba33-4d6a8492eab7
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3S,4R,5R)-4-(hydroxymethyl)-3,5-dimethyloxolan-2-one
• SMILES (Canonical): CC1C(C(OC1=O)C)CO
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H](OC1=O)C)CO
• InChI: InChI=1S/C7H12O3/c1-4-6(3-8)5(2)10-7(4)9/h4-6,8H,3H2,1-2H3/t4-,5+,6-/m0/s1
• InChI Key: RHMRZYPABWGFIW-JKUQZMGJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₇H₁₂O₃
• Molecular Weight: 144.17 g/mol
• Exact Mass: 144.078644241 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.18
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• (3s,4r,5r)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone
• (3S,4R,5R)-4-(Hydroxymethyl)-3,5-dimethyltetrahydrofuran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9861	98.61%
Caco-2	-	0.7370	73.70%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6982	69.82%
OATP2B1 inhibitior	-	0.8524	85.24%
OATP1B1 inhibitior	+	0.8870	88.70%
OATP1B3 inhibitior	+	0.9569	95.69%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9537	95.37%
P-glycoprotein inhibitior	-	0.9700	97.00%
P-glycoprotein substrate	-	0.9680	96.80%
CYP3A4 substrate	-	0.6628	66.28%
CYP2C9 substrate	-	0.7907	79.07%
CYP2D6 substrate	-	0.8812	88.12%
CYP3A4 inhibition	-	0.9469	94.69%
CYP2C9 inhibition	-	0.9627	96.27%
CYP2C19 inhibition	-	0.9248	92.48%
CYP2D6 inhibition	-	0.9621	96.21%
CYP1A2 inhibition	-	0.8198	81.98%
CYP2C8 inhibition	-	0.9943	99.43%
CYP inhibitory promiscuity	-	0.9365	93.65%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6997	69.97%
Eye corrosion	-	0.6873	68.73%
Eye irritation	+	0.8353	83.53%
Skin irritation	+	0.5423	54.23%
Skin corrosion	-	0.8501	85.01%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8585	85.85%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8225	82.25%
Respiratory toxicity	-	0.8444	84.44%
Reproductive toxicity	-	0.7222	72.22%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	+	0.6894	68.94%
Acute Oral Toxicity (c)	III	0.5877	58.77%
Estrogen receptor binding	-	0.8437	84.37%
Androgen receptor binding	-	0.7301	73.01%
Thyroid receptor binding	-	0.8945	89.45%
Glucocorticoid receptor binding	-	0.8496	84.96%
Aromatase binding	-	0.8611	86.11%
PPAR gamma	-	0.8966	89.66%
Honey bee toxicity	-	0.9411	94.11%
Biodegradation	+	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.5863	58.63%

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	86.17%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.13%	97.25%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.94%	86.92%
CHEMBL2581	P07339	Cathepsin D	81.80%	98.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.18%	89.34%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.15%	95.56%

Plants that contains it

• Aster bellidiastrum
• Caragana halodendron
• Davallia divaricata
• Dolomiaea souliei
• Eucalyptus camaldulensis
• Garcinia mangostana
• Ligularia vellerea
• Lonicera hypoleuca
• Nicotiana sylvestris
• Serpocaulon triseriale

Cross-Links

• PubChem: 102125217
• NPASS: NPC280128
• LOTUS: LTS0070024
• wikiData: Q77280898