(3aS,4R,6aS)-6,6a-bis(hydroxymethyl)-4-methoxy-3a,4-dihydro-3H-cyclopenta[b]furan-2-one

Details

• Internal ID: 35fa3403-1b63-4463-ba1e-4f4a6c0a7caf
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3aS,4R,6aS)-6,6a-bis(hydroxymethyl)-4-methoxy-3a,4-dihydro-3H-cyclopenta[b]furan-2-one
• SMILES (Canonical): COC1C=C(C2(C1CC(=O)O2)CO)CO
• SMILES (Isomeric): CO[C@@H]1C=C([C@@]2([C@H]1CC(=O)O2)CO)CO
• InChI: InChI=1S/C10H14O5/c1-14-8-2-6(4-11)10(5-12)7(8)3-9(13)15-10/h2,7-8,11-12H,3-5H2,1H3/t7-,8+,10+/m0/s1
• InChI Key: UWKMXHXTUOGMMZ-QXFUBDJGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄O₅
• Molecular Weight: 214.21 g/mol
• Exact Mass: 214.08412354 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -0.77
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9095	90.95%
Caco-2	-	0.7886	78.86%
Blood Brain Barrier	+	0.6102	61.02%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7261	72.61%
OATP2B1 inhibitior	-	0.8515	85.15%
OATP1B1 inhibitior	+	0.9002	90.02%
OATP1B3 inhibitior	+	0.9604	96.04%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9344	93.44%
P-glycoprotein inhibitior	-	0.9563	95.63%
P-glycoprotein substrate	-	0.9056	90.56%
CYP3A4 substrate	+	0.5230	52.30%
CYP2C9 substrate	-	0.6140	61.40%
CYP2D6 substrate	-	0.8216	82.16%
CYP3A4 inhibition	-	0.9065	90.65%
CYP2C9 inhibition	-	0.8725	87.25%
CYP2C19 inhibition	-	0.8019	80.19%
CYP2D6 inhibition	-	0.9401	94.01%
CYP1A2 inhibition	-	0.7845	78.45%
CYP2C8 inhibition	-	0.8607	86.07%
CYP inhibitory promiscuity	-	0.7915	79.15%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4991	49.91%
Eye corrosion	-	0.9798	97.98%
Eye irritation	-	0.7035	70.35%
Skin irritation	-	0.7341	73.41%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.6424	64.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.6022	60.22%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5787	57.87%
skin sensitisation	-	0.8421	84.21%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.5460	54.60%
Acute Oral Toxicity (c)	III	0.4564	45.64%
Estrogen receptor binding	-	0.6153	61.53%
Androgen receptor binding	-	0.5891	58.91%
Thyroid receptor binding	-	0.7654	76.54%
Glucocorticoid receptor binding	-	0.6034	60.34%
Aromatase binding	-	0.7866	78.66%
PPAR gamma	-	0.7808	78.08%
Honey bee toxicity	-	0.8606	86.06%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.6724	67.24%

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	97.09%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.13%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.87%	85.14%
CHEMBL2581	P07339	Cathepsin D	90.19%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.55%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.39%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.49%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.60%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.86%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.19%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.32%	95.89%

Plants that contains it

• Scrophularia buergeriana

Cross-Links

• PubChem: 102153620
• NPASS: NPC305449
• LOTUS: LTS0015636
• wikiData: Q105280429