(2S,3S)-2-[(1R,2R)-1,2-dihydroxy-2-phenylethyl]-3-ethoxy-2,3-dihydropyran-6-one

Details

• Internal ID: b1db9bfd-1a95-4a04-8d79-f649da6963cf
• Taxonomy: Organoheterocyclic compounds > Pyrans > Pyranones and derivatives > Dihydropyranones
• IUPAC Name: (2S,3S)-2-[(1R,2R)-1,2-dihydroxy-2-phenylethyl]-3-ethoxy-2,3-dihydropyran-6-one
• SMILES (Canonical): CCOC1C=CC(=O)OC1C(C(C2=CC=CC=C2)O)O
• SMILES (Isomeric): CCO[C@H]1C=CC(=O)O[C@H]1[C@@H]([C@@H](C2=CC=CC=C2)O)O
• InChI: InChI=1S/C15H18O5/c1-2-19-11-8-9-12(16)20-15(11)14(18)13(17)10-6-4-3-5-7-10/h3-9,11,13-15,17-18H,2H2,1H3/t11-,13+,14+,15+/m0/s1
• InChI Key: VLWJZPJXEJGGNX-ZGKBOVNRSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.97
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8552	85.52%
Caco-2	-	0.5702	57.02%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7964	79.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9050	90.50%
OATP1B3 inhibitior	+	0.9440	94.40%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7443	74.43%
P-glycoprotein inhibitior	-	0.8249	82.49%
P-glycoprotein substrate	-	0.8961	89.61%
CYP3A4 substrate	-	0.5217	52.17%
CYP2C9 substrate	-	0.8127	81.27%
CYP2D6 substrate	-	0.8838	88.38%
CYP3A4 inhibition	-	0.9125	91.25%
CYP2C9 inhibition	-	0.7158	71.58%
CYP2C19 inhibition	-	0.6469	64.69%
CYP2D6 inhibition	-	0.9398	93.98%
CYP1A2 inhibition	-	0.7018	70.18%
CYP2C8 inhibition	-	0.8909	89.09%
CYP inhibitory promiscuity	+	0.5640	56.40%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.6730	67.30%
Eye corrosion	-	0.9853	98.53%
Eye irritation	-	0.8655	86.55%
Skin irritation	-	0.7311	73.11%
Skin corrosion	-	0.9544	95.44%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8162	81.62%
Micronuclear	+	0.5133	51.33%
Hepatotoxicity	-	0.5268	52.68%
skin sensitisation	-	0.7653	76.53%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.7500	75.00%
Nephrotoxicity	-	0.6084	60.84%
Acute Oral Toxicity (c)	III	0.7966	79.66%
Estrogen receptor binding	+	0.6527	65.27%
Androgen receptor binding	-	0.7530	75.30%
Thyroid receptor binding	-	0.5451	54.51%
Glucocorticoid receptor binding	-	0.5268	52.68%
Aromatase binding	-	0.6818	68.18%
PPAR gamma	-	0.6506	65.06%
Honey bee toxicity	-	0.8626	86.26%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9222	92.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.90%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.10%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.02%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.50%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	89.42%	90.17%
CHEMBL3401	O75469	Pregnane X receptor	88.41%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.31%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.79%	99.17%

Plants that contains it

• Goniothalamus aruensis
• Hexalobus crispiflorus
• Isolona congolana

Cross-Links

• PubChem: 122366245
• LOTUS: LTS0269653
• wikiData: Q104923936