(Z)-3-butylidenephthalide

ID: ALA1765390

Chembl Id: CHEMBL1765390

Cas Number: 76681-73-7

PubChem CID: 5352899

Max Phase: Preclinical

Molecular Formula: C12H12O2

Molecular Weight: 188.23

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (Z)-3-Butylidenephthalide | 3-Butylidenephthalide|3-Butylidene-1(3H)-isobenzofuranone|1(3H)-ISOBENZOFURANONE, 3-BUTYLIDENE-|Ligusticum lactone|(E)-3-Butylidenephthalide|3-Butylidene phthalide|(3E)-3-butylidene-2-benzofuran-1-one|3-Butylidenephthalide, (E)-|CHEMBL1765390|Phthalide, 3-butylidene-|(Z)-3-Butylidenephthalide|n-Butylidene phthalide|FEMA No. 3333|3-Butylidenephthalide, (Z)-|EINECS 208-991-3|NSC 325307|Lingustilide|UNII-S9178G4B3F|AI3-37306|76681-73-7|3-Butylidene-phthalide|cis-ButylideShow More⌵

Canonical SMILES:  CCC/C=C1/OC(=O)c2ccccc21

Standard 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+

Standard InChI Key:  WMBOCUXXNSOQHM-DHZHZOJOSA-N

Alternative Forms

1. Parent:

   

   ALA1765390

   (E)-BUTYLIDENEPHTHALIDE

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 188.23

Molecular Weight (Monoisotopic): 188.0837

AlogP: 3.00

#Rotatable Bonds: 2

Polar Surface Area: 26.30

Molecular Species: ┄

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.02

CX LogD: 3.02

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.67

Np Likeness Score: 1.47

References

1. Brindis F, Rodríguez R, Bye R, González-Andrade M, Mata R..  (2011)  (Z)-3-butylidenephthalide from Ligusticum porteri , an α-glucosidase inhibitor.,  74  (3): [PMID:20879744] [10.1021/np100447a]

2. Tsukamoto T, Nakatani S, Yoshioka Y, Sakai N, Horibe I, Ishikawa Y, Miyazawa M..  (2006)  Comparison of larvicidal, adulticidal and acaricidal activity of two geometrical butylidenephthalide isomers.,  29  (3): [PMID:16508176] [10.1248/bpb.29.592]

3. Mata R, Cristians S, Escandón-Rivera S, Juárez-Reyes K, Rivero-Cruz I..  (2013)  Mexican antidiabetic herbs: valuable sources of inhibitors of α-glucosidases.,  76  (3): [PMID:23398496] [10.1021/np300869g]

4. Luthra T,Banothu V,Adepally U,Kumar K,M S,Chakrabarti S,Maddi SR,Sen S.  (2020)  Discovery of novel pyrido-pyrrolidine hybrid compounds as alpha-glucosidase inhibitors and alternative agent for control of type 1 diabetes.,  188  [PMID:31927314] [10.1016/j.ejmech.2020.112034]

Source

Source(1):

• Scientific Literature