(2S,3S,4R)-3-hydroxy-4-methoxy-2-methyl-7-[(2S,3S)-3-methyloxiran-2-yl]-3,4-dihydro-2H-pyrano[3,2-c]pyran-5-one

Details

• Internal ID: 5f023b9b-8470-42d3-988c-ee1327fb9255
• Taxonomy: Organoheterocyclic compounds > Pyrans > Pyranones and derivatives
• IUPAC Name: (2S,3S,4R)-3-hydroxy-4-methoxy-2-methyl-7-[(2S,3S)-3-methyloxiran-2-yl]-3,4-dihydro-2H-pyrano[3,2-c]pyran-5-one
• SMILES (Canonical): CC1C(C(C2=C(O1)C=C(OC2=O)C3C(O3)C)OC)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@@H](C2=C(O1)C=C(OC2=O)[C@@H]3[C@@H](O3)C)OC)O
• InChI: InChI=1S/C13H16O6/c1-5-10(14)12(16-3)9-7(17-5)4-8(19-13(9)15)11-6(2)18-11/h4-6,10-12,14H,1-3H3/t5-,6-,10-,11-,12+/m0/s1
• InChI Key: YAURGDXRZRXJEE-QLBIMSSWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₆O₆
• Molecular Weight: 268.26 g/mol
• Exact Mass: 268.09468823 g/mol
• Topological Polar Surface Area (TPSA): 77.50 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): 0.93
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9665	96.65%
Caco-2	-	0.5185	51.85%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7394	73.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8959	89.59%
OATP1B3 inhibitior	+	0.9280	92.80%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9247	92.47%
P-glycoprotein inhibitior	-	0.7407	74.07%
P-glycoprotein substrate	-	0.8323	83.23%
CYP3A4 substrate	-	0.5231	52.31%
CYP2C9 substrate	-	0.6203	62.03%
CYP2D6 substrate	-	0.8487	84.87%
CYP3A4 inhibition	-	0.7317	73.17%
CYP2C9 inhibition	-	0.9348	93.48%
CYP2C19 inhibition	-	0.7546	75.46%
CYP2D6 inhibition	-	0.9069	90.69%
CYP1A2 inhibition	-	0.7894	78.94%
CYP2C8 inhibition	-	0.8973	89.73%
CYP inhibitory promiscuity	-	0.6425	64.25%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4360	43.60%
Eye corrosion	-	0.9735	97.35%
Eye irritation	-	0.7262	72.62%
Skin irritation	-	0.6887	68.87%
Skin corrosion	-	0.9737	97.37%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6128	61.28%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8970	89.70%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.7019	70.19%
Acute Oral Toxicity (c)	II	0.5312	53.12%
Estrogen receptor binding	+	0.5415	54.15%
Androgen receptor binding	-	0.4923	49.23%
Thyroid receptor binding	-	0.5895	58.95%
Glucocorticoid receptor binding	-	0.6126	61.26%
Aromatase binding	-	0.5969	59.69%
PPAR gamma	+	0.6643	66.43%
Honey bee toxicity	-	0.8197	81.97%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.8467	84.67%

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	99.58%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.09%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	92.34%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.18%	86.33%
CHEMBL2581	P07339	Cathepsin D	90.15%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.87%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.55%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.43%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.64%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.89%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.72%	99.23%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163006154
• LOTUS: LTS0063682
• wikiData: Q105345594