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

Details

• Internal ID: c079751f-d002-41f3-96ea-3e37d89d1b13
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans
• IUPAC Name: 2-[(3S,4S)-3-hydroxy-3,4,5,6-tetrahydro-1H-cyclopenta[c]furan-4-yl]acetic acid
• SMILES (Canonical): C1CC2=C(C1CC(=O)O)C(OC2)O
• SMILES (Isomeric): C1CC2=C([C@@H]1CC(=O)O)[C@H](OC2)O
• InChI: InChI=1S/C9H12O4/c10-7(11)3-5-1-2-6-4-13-9(12)8(5)6/h5,9,12H,1-4H2,(H,10,11)/t5-,9-/m0/s1
• InChI Key: KWBASGHXHPTPGU-CDUCUWFYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₂O₄
• Molecular Weight: 184.19 g/mol
• Exact Mass: 184.07355886 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): 0.52
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9831	98.31%
Caco-2	-	0.7158	71.58%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7311	73.11%
OATP2B1 inhibitior	-	0.8488	84.88%
OATP1B1 inhibitior	+	0.9520	95.20%
OATP1B3 inhibitior	+	0.9608	96.08%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6613	66.13%
BSEP inhibitior	-	0.9768	97.68%
P-glycoprotein inhibitior	-	0.9828	98.28%
P-glycoprotein substrate	-	0.9158	91.58%
CYP3A4 substrate	-	0.5841	58.41%
CYP2C9 substrate	-	0.5800	58.00%
CYP2D6 substrate	-	0.8471	84.71%
CYP3A4 inhibition	-	0.8765	87.65%
CYP2C9 inhibition	-	0.9164	91.64%
CYP2C19 inhibition	-	0.8455	84.55%
CYP2D6 inhibition	-	0.8817	88.17%
CYP1A2 inhibition	-	0.7021	70.21%
CYP2C8 inhibition	-	0.9236	92.36%
CYP inhibitory promiscuity	-	0.9409	94.09%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6658	66.58%
Eye corrosion	-	0.8754	87.54%
Eye irritation	+	0.9772	97.72%
Skin irritation	-	0.7778	77.78%
Skin corrosion	-	0.9483	94.83%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7455	74.55%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.6224	62.24%
skin sensitisation	-	0.8405	84.05%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7674	76.74%
Acute Oral Toxicity (c)	III	0.6245	62.45%
Estrogen receptor binding	-	0.8174	81.74%
Androgen receptor binding	-	0.7887	78.87%
Thyroid receptor binding	-	0.7866	78.66%
Glucocorticoid receptor binding	-	0.6702	67.02%
Aromatase binding	-	0.7738	77.38%
PPAR gamma	-	0.6254	62.54%
Honey bee toxicity	-	0.9512	95.12%
Biodegradation	+	0.6000	60.00%
Crustacea aquatic toxicity	-	0.8600	86.00%
Fish aquatic toxicity	+	0.8489	84.89%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL226	P30542	Adenosine A1 receptor	90.17%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.99%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.82%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.40%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.98%	95.56%
CHEMBL2581	P07339	Cathepsin D	82.14%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.38%	99.17%

Plants that contains it

• Cistanche deserticola
• Genipa americana

Cross-Links

• PubChem: 5317549
• NPASS: NPC242742
• LOTUS: LTS0007538
• wikiData: Q105146849