(Z)-3-butylidene-7-hydroxyphthalide

Details

• Internal ID: e543e9dd-98f3-410e-9c31-7d12e6a8d96e
• Taxonomy: Organoheterocyclic compounds > Isocoumarans > Isobenzofuranones
• IUPAC Name: (3Z)-3-butylidene-7-hydroxy-2-benzofuran-1-one
• SMILES (Canonical): CCCC=C1C2=C(C(=CC=C2)O)C(=O)O1
• SMILES (Isomeric): CCC/C=C\1/C2=C(C(=CC=C2)O)C(=O)O1
• InChI: InChI=1S/C12H12O3/c1-2-3-7-10-8-5-4-6-9(13)11(8)12(14)15-10/h4-7,13H,2-3H2,1H3/b10-7-
• InChI Key: XLFDJKJEYMKLJX-YFHOEESVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₂O₃
• Molecular Weight: 204.22 g/mol
• Exact Mass: 204.078644241 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 2.70
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• (Z)-3-butylidene-7-hydroxyphthalide
• 93236-67-0
• 3-Butylidene-7-hydroxyphthalide
• 7-hydroxy-3-butylidenephthalide
• (3Z)-3-butylidene-7-hydroxy-2-benzofuran-1(3H)-one
• (3Z)-3-butylidene-7-hydroxyisobenzofuran-1(3H)-one
• 7-Hydroxyligustilide
• C09921
• CHEBI:1458
• SCHEMBL3751329
• SCHEMBL11967649
• DTXSID301025422
• Q27105462
• 1(3H)-Isobenzofuranone, 3-butylidene-7-hydroxy-, (3Z)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9234	92.34%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Plasma membrane	0.5556	55.56%
OATP2B1 inhibitior	-	0.8634	86.34%
OATP1B1 inhibitior	+	0.8581	85.81%
OATP1B3 inhibitior	+	0.9684	96.84%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8940	89.40%
P-glycoprotein inhibitior	-	0.9524	95.24%
P-glycoprotein substrate	-	0.9154	91.54%
CYP3A4 substrate	-	0.5553	55.53%
CYP2C9 substrate	+	0.6383	63.83%
CYP2D6 substrate	-	0.8474	84.74%
CYP3A4 inhibition	-	0.8300	83.00%
CYP2C9 inhibition	-	0.5932	59.32%
CYP2C19 inhibition	+	0.6496	64.96%
CYP2D6 inhibition	-	0.8981	89.81%
CYP1A2 inhibition	+	0.8257	82.57%
CYP2C8 inhibition	-	0.7853	78.53%
CYP inhibitory promiscuity	+	0.6107	61.07%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.4349	43.49%
Eye corrosion	-	0.8726	87.26%
Eye irritation	+	0.9459	94.59%
Skin irritation	-	0.5590	55.90%
Skin corrosion	-	0.9162	91.62%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7095	70.95%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	+	0.6932	69.32%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	-	0.6000	60.00%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.6501	65.01%
Acute Oral Toxicity (c)	III	0.4917	49.17%
Estrogen receptor binding	+	0.7441	74.41%
Androgen receptor binding	+	0.5959	59.59%
Thyroid receptor binding	+	0.5131	51.31%
Glucocorticoid receptor binding	+	0.5642	56.42%
Aromatase binding	-	0.7031	70.31%
PPAR gamma	+	0.7411	74.11%
Honey bee toxicity	-	0.9708	97.08%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9720	97.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.61%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.93%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	93.04%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.69%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.30%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	88.15%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.37%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.55%	89.00%

Plants that contains it

• Angelica acutiloba
• Angelica gigas
• Angelica sinensis
• Conioselinum anthriscoides
• Conioselinum smithii
• Conioselinum tenuissimum
• Levisticum officinale
• Magnolia officinalis

Cross-Links

• PubChem: 5281559
• NPASS: NPC256405
• LOTUS: LTS0230911
• wikiData: Q27105462