ID: ALA350488

Max Phase: Preclinical

Molecular Formula: C11H12O3

Molecular Weight: 192.21

Molecule Type: Small molecule

Representations

Synonyms (1): Methyl 2-(Hydroxy(Phenyl)Methyl)Acrylate
Synonyms from Alternative Forms(1):

Canonical SMILES:  C=C(C(=O)OC)C(O)c1ccccc1

Standard InChI:  InChI=1S/C11H12O3/c1-8(11(13)14-2)10(12)9-6-4-3-5-7-9/h3-7,10,12H,1H2,2H3

Standard InChI Key:  VZGOKIHNKHAORQ-UHFFFAOYSA-N

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

Properties

Molecular Weight: 192.21

Molecular Weight (Monoisotopic): 192.0786

AlogP: 1.45

#Rotatable Bonds: 3

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.61

CX Basic pKa:

CX LogP: 1.81

CX LogD: 1.81

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.58

Np Likeness Score: 0.55

References

1. Kundu MK, Kundu MK, Sundar N, Kumar SK, Bhat SV, Biswas S, Valecha N..  (1999)  Antimalarial activity of 3-hydroxyalkyl-2-methylene-propionic acid derivatives.,  9  (5): [PMID:10201838] [10.1016/s0960-894x(99)00057-8]

2. de Souza RO, Pereira VL, Muzitano MF, Falcão CA, Rossi-Bergmann B, Filho EB, Vasconcellos ML..  (2007)  High selective leishmanicidal activity of 3-hydroxy-2-methylene-3-(4-bromophenyl)propanenitrile and analogous compounds.,  42  (1): [PMID:17010481] [10.1016/j.ejmech.2006.07.013]

3. Lima-Junior CG, Vasconcellos ML..  (2012)  Morita-Baylis-Hillman adducts: biological activities and potentialities to the discovery of new cheaper drugs.,  20  (13): [PMID:22632793] [10.1016/j.bmc.2012.04.061]

4. Ramachandran PV, Helppi MA, Lehmkuhler AL, Marchi JM, Schmidt CM, Yip-Schneider MT..  (2015)  Factors influencing the cytotoxicity of α-methylene-γ-hydroxy esters against pancreatic cancer.,  25  (19): [PMID:26264501] [10.1016/j.bmcl.2015.07.087]

5. Solano LN, Nelson GL, Ronayne CT, Lueth EA, Foxley MA, Jonnalagadda SK, Gurrapu S, Mereddy VR..  (2015)  Synthesis, in vitro, and in vivo evaluation of novel functionalized quaternary ammonium curcuminoids as potential anti-cancer agents.,  25  (24): [PMID:26561365] [10.1016/j.bmcl.2015.10.061]

6. Ronayne CT, Solano LN, Nelson GL, Lueth EA, Hubbard SL, Schumacher TJ, Gardner ZS, Jonnalagadda SK, Gurrapu S, Holy J, Mereddy VR..  (2017)  Synthesis and biological evaluation of 2-alkoxycarbonylallyl esters as potential anticancer agents.,  27  (4): [PMID:28129978] [10.1016/j.bmcl.2017.01.037]

7. da Silva WAV, Rodrigues DC, de Oliveira RG, Mendes RKS, Olegário TR, Rocha JC, Keesen TSL, Lima-Junior CG, Vasconcellos MLAA..  (2016)  Synthesis and activity of novel homodimers of Morita-Baylis-Hillman adducts against Leishmania donovani: A twin drug approach.,  26  (18): [PMID:27520941] [10.1016/j.bmcl.2016.07.022]

Source

Source(1):

• Scientific Literature