methyl (4aR,5S,8aR)-5-hydroxy-2-methylidene-3-oxo-4a,5,6,8a-tetrahydro-4H-1,4-benzoxazine-7-carboxylate

Details

• Internal ID: 1e186935-0870-46e8-9f49-46241d3dfb36
• Taxonomy: Organoheterocyclic compounds > Benzoxazines
• IUPAC Name: methyl (4aR,5S,8aR)-5-hydroxy-2-methylidene-3-oxo-4a,5,6,8a-tetrahydro-4H-1,4-benzoxazine-7-carboxylate
• InChI: InChI=1S/C11H13NO5/c1-5-10(14)12-9-7(13)3-6(11(15)16-2)4-8(9)17-5/h4,7-9,13H,1,3H2,2H3,(H,12,14)/t7-,8+,9+/m0/s1
• InChI Key: MRTLVFNBTBKYFV-DJLDLDEBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₃NO₅
• Molecular Weight: 239.22 g/mol
• Exact Mass: 239.07937252 g/mol
• Topological Polar Surface Area (TPSA): 84.90 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.75
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• CHEBI:197774
• methyl (4aR,5S,8aR)-5-hydroxy-2-methylidene-3-oxo-4a,5,6,8a-tetrahydro-4H-1,4-benzoxazine-7-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8423	84.23%
Caco-2	-	0.7491	74.91%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.3819	38.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8779	87.79%
OATP1B3 inhibitior	+	0.9516	95.16%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9666	96.66%
P-glycoprotein inhibitior	-	0.9663	96.63%
P-glycoprotein substrate	-	0.7201	72.01%
CYP3A4 substrate	+	0.5767	57.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8650	86.50%
CYP3A4 inhibition	-	0.8860	88.60%
CYP2C9 inhibition	-	0.8706	87.06%
CYP2C19 inhibition	-	0.9024	90.24%
CYP2D6 inhibition	-	0.9321	93.21%
CYP1A2 inhibition	-	0.8662	86.62%
CYP2C8 inhibition	-	0.8370	83.70%
CYP inhibitory promiscuity	-	0.9593	95.93%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5095	50.95%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.8715	87.15%
Skin irritation	-	0.7716	77.16%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6564	65.64%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.6565	65.65%
skin sensitisation	-	0.8614	86.14%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5307	53.07%
Acute Oral Toxicity (c)	III	0.5398	53.98%
Estrogen receptor binding	-	0.8025	80.25%
Androgen receptor binding	-	0.8087	80.87%
Thyroid receptor binding	-	0.6948	69.48%
Glucocorticoid receptor binding	-	0.7125	71.25%
Aromatase binding	-	0.8192	81.92%
PPAR gamma	-	0.7488	74.88%
Honey bee toxicity	-	0.8686	86.86%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	-	0.6625	66.25%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.07%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.77%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.66%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.35%	85.14%
CHEMBL2581	P07339	Cathepsin D	89.51%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.86%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	82.96%	91.19%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.14%	93.03%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.09%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.98%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.81%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	80.48%	94.73%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.09%	91.07%

Plants that contains it

• Colocasia esculenta

Cross-Links

• PubChem: 139583162
• LOTUS: LTS0123352
• wikiData: Q105143256