1(3H)-Isobenzofuranone, 3-butyl-4-hydroxy-

Details

• Internal ID: cb368ca8-773c-48ce-93fb-352553de91c9
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Benzofuranones
• IUPAC Name: 3-butyl-4-hydroxy-3H-2-benzofuran-1-one
• SMILES (Canonical): CCCCC1C2=C(C=CC=C2O)C(=O)O1
• SMILES (Isomeric): CCCCC1C2=C(C=CC=C2O)C(=O)O1
• InChI: InChI=1S/C12H14O3/c1-2-3-7-10-11-8(12(14)15-10)5-4-6-9(11)13/h4-6,10,13H,2-3,7H2,1H3
• InChI Key: JQSVHBFDZXZENO-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.24 g/mol
• Exact Mass: 206.094294304 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.79
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 1(3H)-Isobenzofuranone, 3-butyl-4-hydroxy-
• 3-butyl-4-hydroxyphthalide
• 4-hydroxy-3-butylphthalide
• SCHEMBL3986357
• DTXSID10454277
• 3-butyl-4-hydroxy-1,3-dihydro-2-benzofuran-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9967	99.67%
Caco-2	+	0.8985	89.85%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.4740	47.40%
OATP2B1 inhibitior	-	0.8606	86.06%
OATP1B1 inhibitior	+	0.8543	85.43%
OATP1B3 inhibitior	+	0.9657	96.57%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9524	95.24%
P-glycoprotein inhibitior	-	0.9804	98.04%
P-glycoprotein substrate	-	0.7022	70.22%
CYP3A4 substrate	-	0.5627	56.27%
CYP2C9 substrate	-	0.5814	58.14%
CYP2D6 substrate	-	0.8232	82.32%
CYP3A4 inhibition	-	0.9062	90.62%
CYP2C9 inhibition	-	0.6470	64.70%
CYP2C19 inhibition	+	0.5896	58.96%
CYP2D6 inhibition	-	0.9251	92.51%
CYP1A2 inhibition	+	0.6701	67.01%
CYP2C8 inhibition	-	0.7205	72.05%
CYP inhibitory promiscuity	-	0.7499	74.99%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5188	51.88%
Eye corrosion	-	0.9388	93.88%
Eye irritation	+	0.7954	79.54%
Skin irritation	+	0.5085	50.85%
Skin corrosion	-	0.7941	79.41%
Ames mutagenesis	-	0.5037	50.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6431	64.31%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5551	55.51%
skin sensitisation	-	0.5939	59.39%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5937	59.37%
Acute Oral Toxicity (c)	III	0.4421	44.21%
Estrogen receptor binding	-	0.6411	64.11%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5060	50.60%
Glucocorticoid receptor binding	-	0.7308	73.08%
Aromatase binding	-	0.8560	85.60%
PPAR gamma	+	0.7466	74.66%
Honey bee toxicity	-	0.9882	98.82%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9180	91.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.34%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	96.60%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.78%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.27%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.41%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.92%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	87.75%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.59%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.48%	99.17%
CHEMBL1907	P15144	Aminopeptidase N	86.72%	93.31%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.20%	93.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.33%	97.25%

Plants that contains it

• Conioselinum anthriscoides
• Ligusticum officinale

Cross-Links

• PubChem: 11074544
• NPASS: NPC31317