8-[(R)-[(2S)-3,3-dimethyloxiran-2-yl]-hydroxymethyl]-7-methoxychromen-2-one

Details

• Internal ID: 8b825b0b-196e-44c0-86df-b90154857720
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 8-[(R)-[(2S)-3,3-dimethyloxiran-2-yl]-hydroxymethyl]-7-methoxychromen-2-one
• SMILES (Canonical): CC1(C(O1)C(C2=C(C=CC3=C2OC(=O)C=C3)OC)O)C
• SMILES (Isomeric): CC1([C@@H](O1)[C@@H](C2=C(C=CC3=C2OC(=O)C=C3)OC)O)C
• InChI: InChI=1S/C15H16O5/c1-15(2)14(20-15)12(17)11-9(18-3)6-4-8-5-7-10(16)19-13(8)11/h4-7,12,14,17H,1-3H3/t12-,14+/m1/s1
• InChI Key: LRYZVAJCVKCMBC-OCCSQVGLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.28 g/mol
• Exact Mass: 276.09977361 g/mol
• Topological Polar Surface Area (TPSA): 68.30 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.01
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9588	95.88%
Caco-2	+	0.7413	74.13%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6905	69.05%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9410	94.10%
OATP1B3 inhibitior	+	0.9574	95.74%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.4930	49.30%
P-glycoprotein inhibitior	-	0.6431	64.31%
P-glycoprotein substrate	-	0.8731	87.31%
CYP3A4 substrate	+	0.5258	52.58%
CYP2C9 substrate	-	0.6661	66.61%
CYP2D6 substrate	-	0.8159	81.59%
CYP3A4 inhibition	-	0.6454	64.54%
CYP2C9 inhibition	-	0.9348	93.48%
CYP2C19 inhibition	-	0.7127	71.27%
CYP2D6 inhibition	-	0.8464	84.64%
CYP1A2 inhibition	-	0.6976	69.76%
CYP2C8 inhibition	-	0.6794	67.94%
CYP inhibitory promiscuity	-	0.8348	83.48%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4323	43.23%
Eye corrosion	-	0.9841	98.41%
Eye irritation	-	0.6093	60.93%
Skin irritation	-	0.7472	74.72%
Skin corrosion	-	0.9682	96.82%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4688	46.88%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8490	84.90%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6199	61.99%
Acute Oral Toxicity (c)	III	0.5932	59.32%
Estrogen receptor binding	+	0.8394	83.94%
Androgen receptor binding	+	0.6796	67.96%
Thyroid receptor binding	+	0.5471	54.71%
Glucocorticoid receptor binding	+	0.7446	74.46%
Aromatase binding	+	0.7782	77.82%
PPAR gamma	+	0.7199	71.99%
Honey bee toxicity	-	0.8025	80.25%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9349	93.49%

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	95.84%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.49%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.09%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.13%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.88%	95.56%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	88.74%	85.30%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.43%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.92%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.50%	86.33%
CHEMBL1255126	O15151	Protein Mdm4	83.93%	90.20%
CHEMBL2581	P07339	Cathepsin D	82.80%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.47%	96.00%

Plants that contains it

• Ferulopsis hystrix

Cross-Links

• PubChem: 163188174
• LOTUS: LTS0100260
• wikiData: Q105156414