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

Details

• Internal ID: 04e17ff3-1fca-43ad-892d-c083b4d97088
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: 4-hydroxy-6,6a-bis(hydroxymethyl)-3a,4-dihydro-3H-cyclopenta[b]furan-2-one
• SMILES (Canonical): C1C2C(C=C(C2(OC1=O)CO)CO)O
• SMILES (Isomeric): C1C2C(C=C(C2(OC1=O)CO)CO)O
• InChI: InChI=1S/C9H12O5/c10-3-5-1-7(12)6-2-8(13)14-9(5,6)4-11/h1,6-7,10-12H,2-4H2
• InChI Key: GXMPAYJMNREZKW-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₂O₅
• Molecular Weight: 200.19 g/mol
• Exact Mass: 200.06847348 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -1.43
• 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	+	0.9420	94.20%
Caco-2	-	0.9115	91.15%
Blood Brain Barrier	+	0.5781	57.81%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7433	74.33%
OATP2B1 inhibitior	-	0.8541	85.41%
OATP1B1 inhibitior	+	0.9215	92.15%
OATP1B3 inhibitior	+	0.9609	96.09%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9384	93.84%
P-glycoprotein inhibitior	-	0.9809	98.09%
P-glycoprotein substrate	-	0.9175	91.75%
CYP3A4 substrate	-	0.5219	52.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8073	80.73%
CYP3A4 inhibition	-	0.9716	97.16%
CYP2C9 inhibition	-	0.9037	90.37%
CYP2C19 inhibition	-	0.8454	84.54%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.8518	85.18%
CYP2C8 inhibition	-	0.9218	92.18%
CYP inhibitory promiscuity	-	0.9043	90.43%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5270	52.70%
Eye corrosion	-	0.9744	97.44%
Eye irritation	-	0.5730	57.30%
Skin irritation	-	0.7336	73.36%
Skin corrosion	-	0.9334	93.34%
Ames mutagenesis	-	0.5654	56.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7148	71.48%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8727	87.27%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.4917	49.17%
Acute Oral Toxicity (c)	III	0.4161	41.61%
Estrogen receptor binding	-	0.8654	86.54%
Androgen receptor binding	-	0.6018	60.18%
Thyroid receptor binding	-	0.8172	81.72%
Glucocorticoid receptor binding	-	0.6647	66.47%
Aromatase binding	-	0.7264	72.64%
PPAR gamma	-	0.7150	71.50%
Honey bee toxicity	-	0.8494	84.94%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.7751	77.51%

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	95.36%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.69%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.61%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.31%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.53%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.87%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.99%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.14%	97.25%
CHEMBL299	P17252	Protein kinase C alpha	80.82%	98.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.09%	100.00%

Plants that contains it

• Catalpa ovata
• Rehmannia glutinosa

Cross-Links

• PubChem: 5320905
• NPASS: NPC156330
• LOTUS: LTS0116516
• wikiData: Q105108169