(4aS,5R,6S)-4a,5-dihydroxy-3-(methoxymethyl)-6-vinyl-4a,5,6,7-tetrahydro-4H-chromen-4-one

Details

• Internal ID: eb47b9f9-9527-4e9d-8f27-acc846407696
• Taxonomy: Organoheterocyclic compounds > Pyrans > Pyranones and derivatives > Dihydropyranones
• IUPAC Name: (4aS,5R,6S)-6-ethenyl-4a,5-dihydroxy-3-(methoxymethyl)-6,7-dihydro-5H-chromen-4-one
• SMILES (Canonical): COCC1=COC2=CCC(C(C2(C1=O)O)O)C=C
• SMILES (Isomeric): COCC1=COC2=CC[C@H]([C@H]([C@]2(C1=O)O)O)C=C
• InChI: InChI=1S/C13H16O5/c1-3-8-4-5-10-13(16,11(8)14)12(15)9(6-17-2)7-18-10/h3,5,7-8,11,14,16H,1,4,6H2,2H3/t8-,11-,13-/m1/s1
• InChI Key: PTPJFJWUFUTPEZ-XTWCZFFVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₆O₅
• Molecular Weight: 252.26 g/mol
• Exact Mass: 252.09977361 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 0.30
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9296	92.96%
Caco-2	-	0.8029	80.29%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6994	69.94%
OATP2B1 inhibitior	-	0.8615	86.15%
OATP1B1 inhibitior	+	0.8935	89.35%
OATP1B3 inhibitior	+	0.9509	95.09%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9552	95.52%
BSEP inhibitior	-	0.5504	55.04%
P-glycoprotein inhibitior	-	0.9562	95.62%
P-glycoprotein substrate	-	0.8797	87.97%
CYP3A4 substrate	+	0.6133	61.33%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.8020	80.20%
CYP3A4 inhibition	-	0.6957	69.57%
CYP2C9 inhibition	-	0.6735	67.35%
CYP2C19 inhibition	-	0.5921	59.21%
CYP2D6 inhibition	-	0.8474	84.74%
CYP1A2 inhibition	-	0.6228	62.28%
CYP2C8 inhibition	-	0.7208	72.08%
CYP inhibitory promiscuity	-	0.7362	73.62%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6389	63.89%
Eye corrosion	-	0.9780	97.80%
Eye irritation	-	0.8923	89.23%
Skin irritation	-	0.7240	72.40%
Skin corrosion	-	0.9323	93.23%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8648	86.48%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.7792	77.92%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.8157	81.57%
Acute Oral Toxicity (c)	III	0.5244	52.44%
Estrogen receptor binding	+	0.6570	65.70%
Androgen receptor binding	-	0.5893	58.93%
Thyroid receptor binding	-	0.5231	52.31%
Glucocorticoid receptor binding	+	0.6634	66.34%
Aromatase binding	-	0.6145	61.45%
PPAR gamma	-	0.7089	70.89%
Honey bee toxicity	-	0.7411	74.11%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8734	87.34%

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	94.20%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.79%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.66%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.33%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.56%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.70%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.14%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.53%	97.25%
CHEMBL4208	P20618	Proteasome component C5	85.39%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.53%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.88%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.71%	91.07%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 102142198
• LOTUS: LTS0155314
• wikiData: Q75057282