Senkyunolide A

Details

• Internal ID: c08b6bf6-df95-4a2c-ad6e-58f41c412722
• Taxonomy: Organoheterocyclic compounds > Isobenzofurans
• IUPAC Name: (3S)-3-butyl-4,5-dihydro-3H-2-benzofuran-1-one
• SMILES (Canonical): CCCCC1C2=C(C=CCC2)C(=O)O1
• SMILES (Isomeric): CCCC[C@H]1C2=C(C=CCC2)C(=O)O1
• InChI: InChI=1S/C12H16O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7,11H,2-4,6,8H2,1H3/t11-/m0/s1
• InChI Key: ZPIKVDODKLJKIN-NSHDSACASA-N
• Popularity: 44 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.25 g/mol
• Exact Mass: 192.115029749 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.75
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• Senkyunolide
• 63038-10-8
• Sedanenolide
• (S)-Sedanenolide
• (-)-Sedanenolide
• UNII-74QZK813SO
• 74QZK813SO
• (S)-3-Butyl-4,5-dihydroisobenzofuran-1(3H)-one
• 1(3H)-Isobenzofuranone, 3-butyl-4,5-dihydro-, (S)-
• (3S)-3-butyl-4,5-dihydro-3H-2-benzofuran-1-one
• DTXSID40212322
• 1(3H)-Isobenzofuranone, 3-butyl-4,5-dihydro-, (3S)-
• (3S)-3-BUTYL-4,5-DIHYDRO-2-BENZOFURAN-1(3H)-ONE
• Senkyunolide-A
• (3S)-3-Butyl-4,5-dihydro-1(3H)-isobenzofuranone
• 3-butyl-4,5-dihydrophthalide
• SCHEMBL13053469
• DTXCID40134813
• CHEBI:179916
• ZPIKVDODKLJKIN-NSHDSACASA-N
• HY-N0743
• MFCD16660665
• s9513
• AKOS032949093
• MS-23041
• CS-0009775
• C17853
• (3S)-3-butyl-4,5-dihydro-3H-2-benzouran-1-one
• Q27266299
• (3S)-3-butyl-1,3,4,5-tetrahydro-2-benzofuran-1-one
• 1(3H)-Isobenzofuranone, 3-butyl-4,5-dihydro-, (-)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9217	92.17%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Plasma membrane	0.7498	74.98%
OATP2B1 inhibitior	-	0.8536	85.36%
OATP1B1 inhibitior	+	0.9210	92.10%
OATP1B3 inhibitior	+	0.9696	96.96%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.8943	89.43%
P-glycoprotein inhibitior	-	0.9678	96.78%
P-glycoprotein substrate	-	0.8467	84.67%
CYP3A4 substrate	-	0.5195	51.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8688	86.88%
CYP3A4 inhibition	-	0.7440	74.40%
CYP2C9 inhibition	-	0.8831	88.31%
CYP2C19 inhibition	+	0.5244	52.44%
CYP2D6 inhibition	-	0.9170	91.70%
CYP1A2 inhibition	+	0.5662	56.62%
CYP2C8 inhibition	-	0.8693	86.93%
CYP inhibitory promiscuity	-	0.6062	60.62%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5510	55.10%
Eye corrosion	-	0.8050	80.50%
Eye irritation	+	0.7323	73.23%
Skin irritation	-	0.5758	57.58%
Skin corrosion	-	0.9588	95.88%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5094	50.94%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	+	0.6704	67.04%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	-	0.5556	55.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.5446	54.46%
Acute Oral Toxicity (c)	III	0.7598	75.98%
Estrogen receptor binding	-	0.8675	86.75%
Androgen receptor binding	-	0.7274	72.74%
Thyroid receptor binding	-	0.6324	63.24%
Glucocorticoid receptor binding	-	0.8246	82.46%
Aromatase binding	-	0.9010	90.10%
PPAR gamma	-	0.4846	48.46%
Honey bee toxicity	-	0.9629	96.29%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9781	97.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.20%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.16%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.46%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.79%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.79%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.58%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.37%	86.33%
CHEMBL230	P35354	Cyclooxygenase-2	82.76%	89.63%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.91%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	81.73%	94.73%

Plants that contains it

• Angelica acutiloba
• Angelica gigas
• Angelica sinensis
• Conioselinum anthriscoides
• Conioselinum smithii
• Conioselinum tenuissimum
• Crotalaria laburnifolia
• Emilia sonchifolia
• Farfugium japonicum
• Foeniculum vulgare
• Jacobaea renardii
• Jacobaea vulgaris
• Levisticum officinale
• Ligusticum officinale
• Meum athamanticum
• Peucedanum ostruthium
• Scutellaria baicalensis
• Tussilago farfara

Cross-Links

• PubChem: 3085257
• NPASS: NPC90226
• LOTUS: LTS0045033
• wikiData: Q27266299