(5Z)-5-[(2R,3R)-2,3-dihydroxybutylidene]-3-[(2R)-2-hydroxypropyl]furan-2-one

Details

• Internal ID: 9aea4943-e445-458d-ae9b-c9b84b4c7949
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: (5Z)-5-[(2R,3R)-2,3-dihydroxybutylidene]-3-[(2R)-2-hydroxypropyl]furan-2-one
• SMILES (Canonical): CC(CC1=CC(=CC(C(C)O)O)OC1=O)O
• SMILES (Isomeric): C[C@H](CC1=C/C(=C/[C@H]([C@@H](C)O)O)/OC1=O)O
• InChI: InChI=1S/C11H16O5/c1-6(12)3-8-4-9(16-11(8)15)5-10(14)7(2)13/h4-7,10,12-14H,3H2,1-2H3/b9-5-/t6-,7-,10-/m1/s1
• InChI Key: BMCSEOVSJWNEJA-VNVWBWAJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₆O₅
• Molecular Weight: 228.24 g/mol
• Exact Mass: 228.09977361 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.13
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9295	92.95%
Caco-2	-	0.5579	55.79%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6298	62.98%
OATP2B1 inhibitior	-	0.8604	86.04%
OATP1B1 inhibitior	+	0.8850	88.50%
OATP1B3 inhibitior	+	0.9563	95.63%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9338	93.38%
P-glycoprotein inhibitior	-	0.9545	95.45%
P-glycoprotein substrate	-	0.9464	94.64%
CYP3A4 substrate	-	0.6139	61.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8497	84.97%
CYP3A4 inhibition	-	0.9344	93.44%
CYP2C9 inhibition	-	0.9198	91.98%
CYP2C19 inhibition	-	0.8406	84.06%
CYP2D6 inhibition	-	0.9263	92.63%
CYP1A2 inhibition	-	0.8723	87.23%
CYP2C8 inhibition	-	0.9587	95.87%
CYP inhibitory promiscuity	-	0.9183	91.83%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5304	53.04%
Eye corrosion	-	0.9411	94.11%
Eye irritation	-	0.8491	84.91%
Skin irritation	-	0.6089	60.89%
Skin corrosion	-	0.8642	86.42%
Ames mutagenesis	-	0.7437	74.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.8137	81.37%
Micronuclear	-	0.5341	53.41%
Hepatotoxicity	-	0.5131	51.31%
skin sensitisation	-	0.7443	74.43%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	+	0.5513	55.13%
Acute Oral Toxicity (c)	IV	0.4999	49.99%
Estrogen receptor binding	-	0.9103	91.03%
Androgen receptor binding	-	0.7547	75.47%
Thyroid receptor binding	-	0.6482	64.82%
Glucocorticoid receptor binding	-	0.6822	68.22%
Aromatase binding	-	0.8216	82.16%
PPAR gamma	-	0.6630	66.30%
Honey bee toxicity	-	0.9349	93.49%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.8500	85.00%
Fish aquatic toxicity	+	0.7393	73.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.84%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.31%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	92.08%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.58%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.56%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.32%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.34%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.36%	97.25%

Plants that contains it

• Lonicera japonica
• Mimosa aspera

Cross-Links

• PubChem: 163017781
• LOTUS: LTS0092320
• wikiData: Q82918420