(S)-2-[4-Methoxy-3-(4-trifluoromethyl-benzylcarbamoyl)-benzyl]-butyric acid

ID: ALA107789

Chembl Id: CHEMBL107789

Cas Number: 311769-66-1

PubChem CID: 10341445

Max Phase: Preclinical

Molecular Formula: C21H22F3NO4

Molecular Weight: 409.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@H](Cc1ccc(OC)c(C(=O)NCc2ccc(C(F)(F)F)cc2)c1)C(=O)O

Standard InChI:  InChI=1S/C21H22F3NO4/c1-3-15(20(27)28)10-14-6-9-18(29-2)17(11-14)19(26)25-12-13-4-7-16(8-5-13)21(22,23)24/h4-9,11,15H,3,10,12H2,1-2H3,(H,25,26)(H,27,28)/t15-/m0/s1

Standard InChI Key:  YSFRXMSOTXOZQZ-HNNXBMFYSA-N

Alternative Forms

1. Parent:

   

   ALA107789

   Benzenepropanoic acid, alpha-ethyl-4-methoxy-3-((((4-(trifluoromethyl)phenyl)methyl)amino)carbonyl)-, (alphaS)-

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: 409.40

Molecular Weight (Monoisotopic): 409.1501

AlogP: 4.30

#Rotatable Bonds: 8

Polar Surface Area: 75.63

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.02

CX Basic pKa: ┄

CX LogP: 4.56

CX LogD: 1.42

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.68

Np Likeness Score: -0.83

References

1. Miyachi H, Uchiki H..  (2003)  Analysis of the critical structural determinant(s) of species-selective peroxisome proliferator-activated receptor alpha (PPAR alpha)-activation by phenylpropanoic acid-type PPAR alpha agonists.,  13  (19): [PMID:12951082] [10.1016/s0960-894x(03)00715-7]

2. Miyachi H, Nomura M, Tanase T, Suzuki M, Murakami K, Awano K..  (2002)  Enantio-dependent binding and transactivation of optically active phenylpropanoic acid derivatives at human peroxisome proliferator-activated receptor alpha.,  12  (3): [PMID:11814790] [10.1016/s0960-894x(01)00732-6]

3. Nomura M, Tanase T, Ide T, Tsunoda M, Suzuki M, Uchiki H, Murakami K, Miyachi H..  (2003)  Design, synthesis, and evaluation of substituted phenylpropanoic acid derivatives as human peroxisome proliferator activated receptor activators. Discovery of potent and human peroxisome proliferator activated receptor alpha subtype-selective activators.,  46  (17): [PMID:12904063] [10.1021/jm0205144]

4. Kurosumi M, Nishio Y, Osawa S, Kobayashi H, Iwatsubo T, Tomita T, Miyachi H..  (2010)  Novel Notch-sparing gamma-secretase inhibitors derived from a peroxisome proliferator-activated receptor agonist library.,  20  (17): [PMID:20650635] [10.1016/j.bmcl.2010.06.131]

5. Pirat C, Farce A, Lebègue N, Renault N, Furman C, Millet R, Yous S, Speca S, Berthelot P, Desreumaux P, Chavatte P..  (2012)  Targeting peroxisome proliferator-activated receptors (PPARs): development of modulators.,  55  (9): [PMID:22260081] [10.1021/jm101360s]

Source

Source(1):

• Scientific Literature