1-(1-((R)-Hydroxymethyl)-3-{6-[3-(4-methoxy-phenyl)-propionylamino]-indol-1-yl}-propyl)-1H-imidazole-4-carboxylic acid amide

ID: ALA125208

PubChem CID: 11294474

Max Phase: Preclinical

Molecular Formula: C26H29N5O4

Molecular Weight: 475.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CCC(=O)Nc2ccc3ccn(CC[C@H](CO)n4cnc(C(N)=O)c4)c3c2)cc1

Standard InChI:  InChI=1S/C26H29N5O4/c1-35-22-7-2-18(3-8-22)4-9-25(33)29-20-6-5-19-10-12-30(24(19)14-20)13-11-21(16-32)31-15-23(26(27)34)28-17-31/h2-3,5-8,10,12,14-15,17,21,32H,4,9,11,13,16H2,1H3,(H2,27,34)(H,29,33)/t21-/m1/s1

Standard InChI Key:  SXTSBUJREHUEJZ-OAQYLSRUSA-N

Molfile:  

     RDKit          2D

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  2  1  1  0
  3  4  1  0
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 24 21  1  0
 25 27  1  0
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 27 23  1  0
 28 25  2  0
 29 25  1  0
 30 29  2  0
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 32 26  1  0
 33 34  1  0
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 35 32  1  0
  3  6  1  0
 12 10  1  0
 17 24  2  0
 31 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA125208

   1-[(2R)-1-hydroxy-4-{6-[3-(4-methoxyphenyl)propanamido]-1H-indol-1-yl}butan-2-yl]-1H-imidazole-4-carboxamide

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: 475.55

Molecular Weight (Monoisotopic): 475.2220

AlogP: 3.14

#Rotatable Bonds: 11

Polar Surface Area: 124.40

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.50

CX Basic pKa: 3.23

CX LogP: 2.23

CX LogD: 2.23

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.31

Np Likeness Score: -1.03

References

1. Terasaka T, Kinoshita T, Kuno M, Seki N, Tanaka K, Nakanishi I..  (2004)  Structure-based design, synthesis, and structure-activity relationship studies of novel non-nucleoside adenosine deaminase inhibitors.,  47  (15): [PMID:15239652] [10.1021/jm0306374]

Source

Source(1):

• Scientific Literature