4-((2S,4S)-1-((5,7-Dimethyl-1H-indol-4-yl)methyl)-4-ethoxypiperidin-2-yl)benzoic Acid

ID: ALA4644208

PubChem CID: 90467624

Max Phase: Preclinical

Molecular Formula: C25H30N2O3

Molecular Weight: 406.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCO[C@H]1CCN(Cc2c(C)cc(C)c3[nH]ccc23)[C@H](c2ccc(C(=O)O)cc2)C1

Standard InChI:  InChI=1S/C25H30N2O3/c1-4-30-20-10-12-27(23(14-20)18-5-7-19(8-6-18)25(28)29)15-22-16(2)13-17(3)24-21(22)9-11-26-24/h5-9,11,13,20,23,26H,4,10,12,14-15H2,1-3H3,(H,28,29)/t20-,23-/m0/s1

Standard InChI Key:  NHSANTONQVVKKW-REWPJTCUSA-N

Molfile:  

 
     RDKit          2D

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   35.2048  -27.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2019  -26.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4933  -26.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7871  -27.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   33.0062  -26.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5289  -27.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0115  -27.8689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.4949  -28.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9081  -26.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4907  -25.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1971  -25.1570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1944  -24.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9061  -25.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9008  -23.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6125  -25.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6098  -24.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4892  -23.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4879  -23.1149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7797  -22.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0724  -23.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0777  -23.9410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7864  -24.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3162  -23.9244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3628  -22.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3591  -21.8971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6570  -23.1261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.0252  -24.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7316  -23.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 14 16  1  0
 15 17  1  0
 16 18  1  0
 17 18  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
 14 19  1  6
 18 25  1  1
 22 26  1  0
 26 27  2  0
 26 28  1  0
 25 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4644208

   4-[(2S,4S)-1-[(5,7-dimethyl-1H-indol-4-yl)methyl]-4-ethoxypiperidin-2-yl]benzoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 406.53

Molecular Weight (Monoisotopic): 406.2256

AlogP: 5.23

#Rotatable Bonds: 6

Polar Surface Area: 65.56

Molecular Species: ZWITTERION

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.68

CX Basic pKa: 9.48

CX LogP: 2.07

CX LogD: 2.07

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.59

Np Likeness Score: -0.30

References

1. Mainolfi N, Ehara T, Karki RG, Anderson K, Mac Sweeney A, Liao SM, Argikar UA, Jendza K, Zhang C, Powers J, Klosowski DW, Crowley M, Kawanami T, Ding J, April M, Forster C, Serrano-Wu M, Capparelli M, Ramqaj R, Solovay C, Cumin F, Smith TM, Ferrara L, Lee W, Long D, Prentiss M, De Erkenez A, Yang L, Liu F, Sellner H, Sirockin F, Valeur E, Erbel P, Ostermeier D, Ramage P, Gerhartz B, Schubart A, Flohr S, Gradoux N, Feifel R, Vogg B, Wiesmann C, Maibaum J, Eder J, Sedrani R, Harrison RA, Mogi M, Jaffee BD, Adams CM..  (2020)  Discovery of 4-((2S,4S)-4-Ethoxy-1-((5-methoxy-7-methyl-1H-indol-4-yl)methyl)piperidin-2-yl)benzoic Acid (LNP023), a Factor B Inhibitor Specifically Designed To Be Applicable to Treating a Diverse Array of Complement Mediated Diseases.,  63  (11): [PMID:32073845] [10.1021/acs.jmedchem.9b01870]

Source

Source(1):

• Scientific Literature