(2R)-2alpha-Methyl-3,4,7,8-tetrahydro-2H,5H-pyrano[4,3-b]-1,4-oxazine-3,5-dione

Details

• Internal ID: 59185d76-0509-4d5b-99d9-c37c21d739ae
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (2R)-2-methyl-7,8-dihydro-4H-pyrano[4,3-b][1,4]oxazine-3,5-dione
• SMILES (Canonical): CC1C(=O)NC2=C(O1)CCOC2=O
• SMILES (Isomeric): C[C@@H]1C(=O)NC2=C(O1)CCOC2=O
• InChI: InChI=1S/C8H9NO4/c1-4-7(10)9-6-5(13-4)2-3-12-8(6)11/h4H,2-3H2,1H3,(H,9,10)/t4-/m1/s1
• InChI Key: QYMDEMHOFUKUMT-SCSAIBSYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₉NO₄
• Molecular Weight: 183.16 g/mol
• Exact Mass: 183.05315777 g/mol
• Topological Polar Surface Area (TPSA): 64.60 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.32
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• (2R)-2alpha-Methyl-3,4,7,8-tetrahydro-2H,5H-pyrano[4,3-b]-1,4-oxazine-3,5-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9400	94.00%
Caco-2	-	0.5876	58.76%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7513	75.13%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.9537	95.37%
OATP1B3 inhibitior	+	0.9468	94.68%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.9395	93.95%
P-glycoprotein inhibitior	-	0.9672	96.72%
P-glycoprotein substrate	-	0.9127	91.27%
CYP3A4 substrate	-	0.5898	58.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8907	89.07%
CYP3A4 inhibition	-	0.9618	96.18%
CYP2C9 inhibition	-	0.7880	78.80%
CYP2C19 inhibition	-	0.7559	75.59%
CYP2D6 inhibition	-	0.9294	92.94%
CYP1A2 inhibition	-	0.7041	70.41%
CYP2C8 inhibition	-	0.9639	96.39%
CYP inhibitory promiscuity	-	0.8179	81.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5094	50.94%
Eye corrosion	-	0.9835	98.35%
Eye irritation	-	0.6099	60.99%
Skin irritation	-	0.7568	75.68%
Skin corrosion	-	0.9252	92.52%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6152	61.52%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.8566	85.66%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5375	53.75%
Acute Oral Toxicity (c)	III	0.5768	57.68%
Estrogen receptor binding	-	0.7416	74.16%
Androgen receptor binding	-	0.4890	48.90%
Thyroid receptor binding	-	0.6845	68.45%
Glucocorticoid receptor binding	-	0.7178	71.78%
Aromatase binding	-	0.8536	85.36%
PPAR gamma	-	0.7925	79.25%
Honey bee toxicity	-	0.8882	88.82%
Biodegradation	+	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	-	0.6620	66.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.85%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.78%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.20%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.86%	97.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.46%	93.40%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.85%	97.25%
CHEMBL2581	P07339	Cathepsin D	84.66%	98.95%
CHEMBL299	P17252	Protein kinase C alpha	84.51%	98.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.77%	96.09%
CHEMBL4588	P22894	Matrix metalloproteinase 8	83.54%	94.66%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.92%	90.08%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.79%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.56%	94.45%

Plants that contains it

• Isatis tinctoria

Cross-Links

• PubChem: 60156056
• NPASS: NPC737