[4-({(3,5-dimethoxy-4-methylbenzoyl)[(2E)-3-phenyl-2-propen-1-yl]amino}methyl)phenyl]acetic acid

ID: ALA3973793

PubChem CID: 134153933

Max Phase: Preclinical

Molecular Formula: C28H29NO5

Molecular Weight: 459.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)N(C/C=C/c2ccccc2)Cc2ccc(CC(=O)O)cc2)cc(OC)c1C

Standard InChI:  InChI=1S/C28H29NO5/c1-20-25(33-2)17-24(18-26(20)34-3)28(32)29(15-7-10-21-8-5-4-6-9-21)19-23-13-11-22(12-14-23)16-27(30)31/h4-14,17-18H,15-16,19H2,1-3H3,(H,30,31)/b10-7+

Standard InChI Key:  CGUDRHQQPYHOID-JXMROGBWSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
    3.0156   -3.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0144   -4.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7225   -4.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4321   -4.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4293   -3.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7207   -2.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1355   -2.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8447   -3.1855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1324   -1.9624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5509   -2.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2601   -3.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9663   -2.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7223   -5.2401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0145   -5.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078   -2.7860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6002   -3.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3064   -4.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8478   -4.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5570   -4.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5585   -5.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2669   -5.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9740   -5.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9683   -4.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2593   -3.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6755   -3.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6758   -3.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3842   -4.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0913   -3.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0856   -3.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3766   -2.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6838   -5.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6880   -6.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3978   -6.8478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9824   -6.8550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
  3 13  1  0
 13 14  1  0
  1 15  1  0
 15 16  1  0
  2 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 12 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 22 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3973793

   ---

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: 459.54

Molecular Weight (Monoisotopic): 459.2046

AlogP: 5.00

#Rotatable Bonds: 10

Polar Surface Area: 76.07

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.09

CX Basic pKa: ┄

CX LogP: 5.17

CX LogD: 2.06

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.46

Np Likeness Score: -0.51

References

1. Terakado M, Suzuki H, Hashimura K, Tanaka M, Ueda H, Kohno H, Fujimoto T, Saga H, Nakade S, Habashita H, Takaoka Y, Seko T..  (2016)  Discovery of ONO-7300243 from a Novel Class of Lysophosphatidic Acid Receptor 1 Antagonists: From Hit to Lead.,  7  (10): [PMID:27774128] [10.1021/acsmedchemlett.6b00225]

2. Terakado M, Suzuki H, Hashimura K, Tanaka M, Ueda H, Hirai K, Asada M, Ikura M, Matsunaga N, Saga H, Shinozaki K, Karakawa N, Takada Y, Minami M, Egashira H, Sugiura Y, Yamada M, Nakade S, Takaoka Y..  (2017)  Discovery of a Slow Tight Binding LPA1 Antagonist (ONO-0300302) for the Treatment of Benign Prostatic Hyperplasia.,  8  (12): [PMID:29259748] [10.1021/acsmedchemlett.7b00383]

Source

Source(1):

• Scientific Literature