1-{1-((R)-Hydroxymethyl)-3-[6-(4-p-tolyl-butyrylamino)-indol-1-yl]-propyl}-1H-imidazole-4-carboxylic acid amide

ID: ALA124728

PubChem CID: 11225254

Max Phase: Preclinical

Molecular Formula: C27H31N5O3

Molecular Weight: 473.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(CCCC(=O)Nc2ccc3ccn(CC[C@H](CO)n4cnc(C(N)=O)c4)c3c2)cc1

Standard InChI:  InChI=1S/C27H31N5O3/c1-19-5-7-20(8-6-19)3-2-4-26(34)30-22-10-9-21-11-13-31(25(21)15-22)14-12-23(17-33)32-16-24(27(28)35)29-18-32/h5-11,13,15-16,18,23,33H,2-4,12,14,17H2,1H3,(H2,28,35)(H,30,34)/t23-/m1/s1

Standard InChI Key:  YYZBYPRSQIYLES-HSZRJFAPSA-N

Molfile:  

     RDKit          2D

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 32 30  1  0
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  3  6  1  0
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 17 23  2  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA124728

   1-[(2R)-1-hydroxy-4-{6-[4-(4-methylphenyl)butanamido]-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: 473.58

Molecular Weight (Monoisotopic): 473.2427

AlogP: 3.83

#Rotatable Bonds: 11

Polar Surface Area: 115.17

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.51

CX Basic pKa: 3.23

CX LogP: 3.34

CX LogD: 3.34

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.31

Np Likeness Score: -1.10

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