Rugulactone

Details

• Internal ID: 55c5aae6-38ff-49f5-a077-22faf1cb6de7
• Taxonomy: Organoheterocyclic compounds > Pyrans > Pyranones and derivatives > Dihydropyranones
• IUPAC Name: (2R)-2-[(E)-4-oxo-6-phenylhex-2-enyl]-2,3-dihydropyran-6-one
• SMILES (Canonical): C1C=CC(=O)OC1CC=CC(=O)CCC2=CC=CC=C2
• SMILES (Isomeric): C1C=CC(=O)O[C@@H]1C/C=C/C(=O)CCC2=CC=CC=C2
• InChI: InChI=1S/C17H18O3/c18-15(13-12-14-6-2-1-3-7-14)8-4-9-16-10-5-11-17(19)20-16/h1-8,11,16H,9-10,12-13H2/b8-4+/t16-/m1/s1
• InChI Key: IRHVCJVCISOATN-KZJSRBBCSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈O₃
• Molecular Weight: 270.32 g/mol
• Exact Mass: 270.125594432 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.01
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• (R)-rugulactone
• R-RUGULACTONE
• CHEMBL1253688
• (6R)-6-[(2E)-4-Oxo-6-phenyl-2-hexen-1-yl]-5,6-dihydro-2H-pyran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9876	98.76%
Caco-2	-	0.6532	65.32%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7018	70.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9224	92.24%
OATP1B3 inhibitior	+	0.9625	96.25%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.6318	63.18%
P-glycoprotein inhibitior	-	0.8844	88.44%
P-glycoprotein substrate	-	0.8457	84.57%
CYP3A4 substrate	+	0.5093	50.93%
CYP2C9 substrate	-	0.6338	63.38%
CYP2D6 substrate	-	0.8636	86.36%
CYP3A4 inhibition	-	0.7456	74.56%
CYP2C9 inhibition	-	0.6568	65.68%
CYP2C19 inhibition	+	0.6180	61.80%
CYP2D6 inhibition	-	0.9270	92.70%
CYP1A2 inhibition	-	0.8615	86.15%
CYP2C8 inhibition	-	0.6637	66.37%
CYP inhibitory promiscuity	-	0.7772	77.72%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8228	82.28%
Carcinogenicity (trinary)	Non-required	0.6433	64.33%
Eye corrosion	-	0.8436	84.36%
Eye irritation	-	0.6569	65.69%
Skin irritation	-	0.5867	58.67%
Skin corrosion	-	0.9437	94.37%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4645	46.45%
Micronuclear	-	0.8315	83.15%
Hepatotoxicity	+	0.5306	53.06%
skin sensitisation	-	0.7127	71.27%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.6311	63.11%
Acute Oral Toxicity (c)	III	0.5412	54.12%
Estrogen receptor binding	+	0.7776	77.76%
Androgen receptor binding	-	0.6890	68.90%
Thyroid receptor binding	-	0.7213	72.13%
Glucocorticoid receptor binding	-	0.7603	76.03%
Aromatase binding	+	0.6784	67.84%
PPAR gamma	-	0.4946	49.46%
Honey bee toxicity	-	0.9006	90.06%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8264	82.64%

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	94.31%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.59%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.72%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.58%	86.33%
CHEMBL2581	P07339	Cathepsin D	84.94%	98.95%
CHEMBL5805	Q9NR97	Toll-like receptor 8	84.66%	96.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.98%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.79%	95.50%

Plants that contains it

• Cryptocarya rugulosa

Cross-Links

• PubChem: 52948504
• LOTUS: LTS0145100
• wikiData: Q105118874