Obolactone

Details

• Internal ID: 67b5cff1-eb11-4d9c-95ea-b26605be2b5b
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Styrenes
• IUPAC Name: (2R)-2-[[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]-6-[(E)-2-phenylethenyl]-2,3-dihydropyran-4-one
• SMILES (Canonical): C1C=CC(=O)OC1CC2CC(=O)C=C(O2)C=CC3=CC=CC=C3
• SMILES (Isomeric): C1C=CC(=O)O[C@H]1C[C@@H]2CC(=O)C=C(O2)/C=C/C3=CC=CC=C3
• InChI: InChI=1S/C19H18O4/c20-15-11-17(10-9-14-5-2-1-3-6-14)22-18(12-15)13-16-7-4-8-19(21)23-16/h1-6,8-11,16,18H,7,12-13H2/b10-9+/t16-,18+/m1/s1
• InChI Key: NZGGCMIUTMKVIG-WADNSWHXSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₄
• Molecular Weight: 310.30 g/mol
• Exact Mass: 310.12050905 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.20
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 712272-88-3
• (2R)-2-[[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]-6-[(E)-2-phenylethenyl]-2,3-dihydropyran-4-one
• CHEBI:66803
• (6R)-6-({(2R)-4-oxo-6-[(E)-2-phenylethenyl]-3,4-dihydro-2H-pyran-2-yl}methyl)-5,6-dihydro-2H-pyran-2-one
• CHEMBL452184
• SCHEMBL2328947
• AKOS040762136
• Q27135435

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9745	97.45%
Caco-2	+	0.6145	61.45%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8345	83.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8774	87.74%
OATP1B3 inhibitior	+	0.9639	96.39%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7402	74.02%
P-glycoprotein inhibitior	-	0.6943	69.43%
P-glycoprotein substrate	-	0.7735	77.35%
CYP3A4 substrate	-	0.5151	51.51%
CYP2C9 substrate	-	0.6291	62.91%
CYP2D6 substrate	-	0.8662	86.62%
CYP3A4 inhibition	-	0.5541	55.41%
CYP2C9 inhibition	-	0.6851	68.51%
CYP2C19 inhibition	-	0.5083	50.83%
CYP2D6 inhibition	-	0.9068	90.68%
CYP1A2 inhibition	-	0.8895	88.95%
CYP2C8 inhibition	-	0.7227	72.27%
CYP inhibitory promiscuity	-	0.6198	61.98%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7958	79.58%
Carcinogenicity (trinary)	Non-required	0.6062	60.62%
Eye corrosion	-	0.9001	90.01%
Eye irritation	-	0.7368	73.68%
Skin irritation	-	0.5494	54.94%
Skin corrosion	-	0.9326	93.26%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7027	70.27%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.7052	70.52%
skin sensitisation	-	0.7607	76.07%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	-	0.6000	60.00%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	+	0.5061	50.61%
Acute Oral Toxicity (c)	III	0.4876	48.76%
Estrogen receptor binding	+	0.8651	86.51%
Androgen receptor binding	+	0.7352	73.52%
Thyroid receptor binding	-	0.6575	65.75%
Glucocorticoid receptor binding	-	0.7023	70.23%
Aromatase binding	+	0.7649	76.49%
PPAR gamma	-	0.4902	49.02%
Honey bee toxicity	-	0.8689	86.89%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9112	91.12%

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	94.59%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.07%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.26%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.74%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.93%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.69%	96.00%
CHEMBL5805	Q9NR97	Toll-like receptor 8	81.02%	96.25%

Plants that contains it

• Cryptocarya obovata

Cross-Links

• PubChem: 11370316
• LOTUS: LTS0134052
• wikiData: Q27135435