2-acetyloxy-2-[(3S,4R)-3-hydroxy-3,4,5,6-tetrahydro-1H-cyclopenta[c]furan-4-yl]acetic acid

Details

• Internal ID: a5a7d7d0-9c20-41d2-a907-5eb43396cac7
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Dicarboxylic acids and derivatives
• IUPAC Name: 2-acetyloxy-2-[(3S,4R)-3-hydroxy-3,4,5,6-tetrahydro-1H-cyclopenta[c]furan-4-yl]acetic acid
• SMILES (Canonical): CC(=O)OC(C1CCC2=C1C(OC2)O)C(=O)O
• SMILES (Isomeric): CC(=O)OC([C@@H]1CCC2=C1[C@H](OC2)O)C(=O)O
• InChI: InChI=1S/C11H14O6/c1-5(12)17-9(10(13)14)7-3-2-6-4-16-11(15)8(6)7/h7,9,11,15H,2-4H2,1H3,(H,13,14)/t7-,9?,11+/m1/s1
• InChI Key: GEWMGBJPZDGMSS-DLSRMIIKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₄O₆
• Molecular Weight: 242.22 g/mol
• Exact Mass: 242.07903816 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): 0.06
• 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	+	0.9774	97.74%
Caco-2	-	0.8674	86.74%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8794	87.94%
OATP2B1 inhibitior	-	0.8509	85.09%
OATP1B1 inhibitior	+	0.9481	94.81%
OATP1B3 inhibitior	+	0.9585	95.85%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9662	96.62%
P-glycoprotein inhibitior	-	0.9466	94.66%
P-glycoprotein substrate	-	0.8395	83.95%
CYP3A4 substrate	+	0.5330	53.30%
CYP2C9 substrate	-	0.7936	79.36%
CYP2D6 substrate	-	0.8786	87.86%
CYP3A4 inhibition	-	0.9259	92.59%
CYP2C9 inhibition	-	0.7041	70.41%
CYP2C19 inhibition	-	0.7546	75.46%
CYP2D6 inhibition	-	0.8647	86.47%
CYP1A2 inhibition	+	0.6458	64.58%
CYP2C8 inhibition	-	0.9012	90.12%
CYP inhibitory promiscuity	-	0.8496	84.96%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.6036	60.36%
Eye corrosion	-	0.8992	89.92%
Eye irritation	-	0.8998	89.98%
Skin irritation	-	0.7603	76.03%
Skin corrosion	-	0.9367	93.67%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8480	84.80%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.5450	54.50%
skin sensitisation	-	0.8364	83.64%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.5686	56.86%
Acute Oral Toxicity (c)	III	0.5096	50.96%
Estrogen receptor binding	-	0.6206	62.06%
Androgen receptor binding	-	0.6769	67.69%
Thyroid receptor binding	-	0.7207	72.07%
Glucocorticoid receptor binding	-	0.5633	56.33%
Aromatase binding	-	0.8524	85.24%
PPAR gamma	-	0.7519	75.19%
Honey bee toxicity	-	0.8127	81.27%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6855	68.55%
Fish aquatic toxicity	+	0.9341	93.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	93.60%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.90%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.96%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.64%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.44%	91.11%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.64%	93.56%
CHEMBL340	P08684	Cytochrome P450 3A4	82.75%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.85%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.65%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.52%	99.17%

Plants that contains it

• Gardenia jasminoides
• Genipa americana

Cross-Links

• PubChem: 5317551
• NPASS: NPC221396
• LOTUS: LTS0171650
• wikiData: Q105106402