3-Butylidenephthalide

Details

• Internal ID: 62dfbeaf-32aa-4fa5-b4e1-f3efaae2e153
• Taxonomy: Organoheterocyclic compounds > Isocoumarans > Isobenzofuranones
• IUPAC Name: (3Z)-3-butylidene-2-benzofuran-1-one
• SMILES (Canonical): CCCC=C1C2=CC=CC=C2C(=O)O1
• SMILES (Isomeric): CCC/C=C\1/C2=CC=CC=C2C(=O)O1
• InChI: InChI=1S/C12H12O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-8H,2-3H2,1H3/b11-8-
• InChI Key: WMBOCUXXNSOQHM-FLIBITNWSA-N
• Popularity: 162 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₂O₂
• Molecular Weight: 188.22 g/mol
• Exact Mass: 188.083729621 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.00
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• n-butylidenephthalide
• 3-Butylidenephthalide
• 72917-31-8
• 551-08-6
• Butylidenephthalide
• 1(3H)-Isobenzofuranone, 3-butylidene-, (3Z)-
• (Z)-3-Butylidenephthalide
• 3-Butylideneisobenzofuran-1(3H)-one
• Z-butylidenephthalide
• (3Z)-3-butylidene-2-benzofuran-1-one
• BdPh
• 3-Butylidenephthalide-d8
• (Z)-3-butylideneisobenzofuran-1(3H)-one
• 3-Butylidenephthalide, (Z)-
• CHEMBL249592
• UNII-6GM611H175
• (3Z)-3-Butylidene-2-benzofuran-1(3H)-one
• CHEBI:68233
• 6GM611H175
• NSC-325307
• 3-Butylidene phthalide
• Butylidene phthalide
• 3 - butylidenephthalide
• 1795142-65-2
• e-butylidenephthalide
• (E)-Butylidene phthalide
• trans-3n-butylidenephthalide
• SCHEMBL290482
• DTXSID30993698
• BUTYLIDENEPHTHALIDE, (Z)-
• WMBOCUXXNSOQHM-FLIBITNWSA-N
• HY-N0336
• BDBM50241315
• MFCD00047319
• NSC325307
• s6493
• (3Z)-3-butylideneisobenzofuran-1-one
• AKOS024286816
• AC-34145
• BS-49282
• CS-0008897
• A14633
• C16924
• F17666
• (3Z)-3-BUTYLIDENE-1(3H)-ISOBENZOFURANONE
• 1(3H)-ISOBENZOFURANONE, 3-BUTYLIDENE-, (Z)-
• Q27136726
• InChI=1/C12H12O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-8H,2-3H2,1H3/b11-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9604	96.04%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.8143	81.43%
Subcellular localzation	Plasma membrane	0.6367	63.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9100	91.00%
OATP1B3 inhibitior	+	0.9661	96.61%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8335	83.35%
P-glycoprotein inhibitior	-	0.9683	96.83%
P-glycoprotein substrate	-	0.9569	95.69%
CYP3A4 substrate	-	0.6280	62.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7943	79.43%
CYP3A4 inhibition	-	0.8671	86.71%
CYP2C9 inhibition	-	0.6154	61.54%
CYP2C19 inhibition	+	0.8076	80.76%
CYP2D6 inhibition	-	0.8949	89.49%
CYP1A2 inhibition	+	0.8424	84.24%
CYP2C8 inhibition	-	0.8644	86.44%
CYP inhibitory promiscuity	+	0.7164	71.64%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.4432	44.32%
Eye corrosion	-	0.7775	77.75%
Eye irritation	+	0.9738	97.38%
Skin irritation	-	0.6052	60.52%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6135	61.35%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	+	0.8936	89.36%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	-	0.7111	71.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.6447	64.47%
Acute Oral Toxicity (c)	III	0.8021	80.21%
Estrogen receptor binding	-	0.6439	64.39%
Androgen receptor binding	-	0.5376	53.76%
Thyroid receptor binding	-	0.5971	59.71%
Glucocorticoid receptor binding	-	0.8303	83.03%
Aromatase binding	-	0.6916	69.16%
PPAR gamma	-	0.7024	70.24%
Honey bee toxicity	-	0.9386	93.86%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9590	95.90%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL6007	O75762	Transient receptor potential cation channel subfamily A member 1	23000 nM	IC50	PMID: 23993334

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.69%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.51%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	89.83%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.20%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.43%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.29%	82.69%

Plants that contains it

• Angelica acutiloba
• Angelica gigas
• Angelica sinensis
• Conioselinum anthriscoides
• Conioselinum smithii
• Conioselinum tenuissimum
• Ligusticum officinale
• Ligusticum porteri
• Ligusticum striatum
• Lonicera japonica

Cross-Links

• PubChem: 642376
• NPASS: NPC30594
• ChEMBL: CHEMBL249592
• LOTUS: LTS0020784
• wikiData: Q27136726