(E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid butyl ester

ID: ALA29489

Cas Number: 136944-10-0

PubChem CID: 9991705

Max Phase: Preclinical

Molecular Formula: C13H16O4

Molecular Weight: 236.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Butyl 1-(3',4'-Dihydroxyphenyl)Propenate | Butyl 3-(3,4-Dihydroxyphenyl)Acrylate | Butyl Caffeate | Butyl 3-(3,4-dihydroxyphenyl)acrylate|22020-28-6|Butyl Caffeate|E-Caffeic acid n-butyl ester|Butyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate|136944-10-0|caffeic acid butyl ester|CHEMBL29489|SCHEMBL1879822|DTXSID20433816|DBBCBZIFZYILRL-FNORWQNLSA-N|BDBM50276912|Butyl3-(3,4-dihydroxyphenyl)acrylate|Butyl 1-(3',4'-Dihydroxyphenyl)Propenate|butyl (E)-3-(3,4-dihydroxyphenyl)acrylate|Butyl-3-(3,4-dihydroShow More⌵

Canonical SMILES:  CCCCOC(=O)/C=C/c1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C13H16O4/c1-2-3-8-17-13(16)7-5-10-4-6-11(14)12(15)9-10/h4-7,9,14-15H,2-3,8H2,1H3/b7-5+

Standard InChI Key:  DBBCBZIFZYILRL-FNORWQNLSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
   -1.1442   -7.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8647   -7.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5751   -7.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5661   -8.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8409   -9.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1336   -8.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2753   -9.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8287   -9.8484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345   -7.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4438   -6.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2660   -6.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2566   -5.2869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9851   -6.5162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6948   -6.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4139   -6.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1237   -6.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8428   -6.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0
  4  5  1  0
  9 10  2  0
  2  3  1  0
 10 11  1  0
  5  6  2  0
 11 12  2  0
  6  1  1  0
 11 13  1  0
  1  2  2  0
 13 14  1  0
  4  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  1  0
  5  8  1  0
 16 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA29489

   BUTYL CAFFEATE

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: 236.27

Molecular Weight (Monoisotopic): 236.1049

AlogP: 2.45

#Rotatable Bonds: 5

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.21

CX Basic pKa: ┄

CX LogP: 3.23

CX LogD: 3.23

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.36

Np Likeness Score: 0.85

References

1. Blank VC, Poli C, Marder M, Roguin LP..  (2004)  Antiproliferative activity of various flavonoids and related compounds: additive effect of interferon-alpha2b.,  14  (1): [PMID:14684314] [10.1016/j.bmcl.2003.10.029]

2. Xia CN, Li HB, Liu F, Hu WX..  (2008)  Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines.,  18  (24): [PMID:18952420] [10.1016/j.bmcl.2008.10.046]

3. Uwai K, Osanai Y, Imaizumi T, Kanno S, Takeshita M, Ishikawa M..  (2008)  Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages.,  16  (16): [PMID:18667320] [10.1016/j.bmc.2008.07.006]

4. de Campos Buzzi F, Franzoi CL, Antonini G, Fracasso M, Cechinel Filho V, Yunes RA, Niero R..  (2009)  Antinociceptive properties of caffeic acid derivatives in mice.,  44  (11): [PMID:19628311] [10.1016/j.ejmech.2009.06.029]

5. Li W, Li N, Tang Y, Li B, Liu L, Zhang X, Fu H, Duan JA..  (2012)  Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer.,  22  (19): [PMID:22954735] [10.1016/j.bmcl.2012.08.038]

6. Sanderson JT, Clabault H, Patton C, Lassalle-Claux G, Jean-François J, Paré AF, Hébert MJ, Surette ME, Touaibia M..  (2013)  Antiproliferative, antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells.,  21  (22): [PMID:24080105] [10.1016/j.bmc.2013.08.057]

7. Chen HZ, Chen YB, Lv YP, Zeng F, Zhang J, Zhou YL, Li HB, Chen LF, Zhou BJ, Gao JR, Xia CN..  (2014)  Synthesis and antitumor activity of feruloyl and caffeoyl derivatives.,  24  (18): [PMID:25160837] [10.1016/j.bmcl.2014.08.024]

8. Taguchi R, Hatayama K, Takahashi T, Hayashi T, Sato Y, Sato D, Ohta K, Nakano H, Seki C, Endo Y, Tokuraku K, Uwai K..  (2017)  Structure-activity relations of rosmarinic acid derivatives for the amyloid β aggregation inhibition and antioxidant properties.,  138  [PMID:28759879] [10.1016/j.ejmech.2017.07.026]

9. Ghobadi E, Ghanbarimasir Z, Emami S..  (2021)  A review on the structures and biological activities of anti-Helicobacter pylori agents.,  223  [PMID:34218084] [10.1016/j.ejmech.2021.113669]

Source

Source(1):

• Scientific Literature