(R)-N-(2-Amino-1-(5-(hydroxymethyl)thiazol-2-yl)ethyl)-5-(5-chloropyridin-2-yl)-3-methyl-1H-pyrrole-2-carboxamide

ID: ALA4476838

PubChem CID: 155538607

Max Phase: Preclinical

Molecular Formula: C17H18ClN5O2S

Molecular Weight: 391.88

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2ccc(Cl)cn2)[nH]c1C(=O)N[C@H](CN)c1ncc(CO)s1

Standard InChI:  InChI=1S/C17H18ClN5O2S/c1-9-4-13(12-3-2-10(18)6-20-12)22-15(9)16(25)23-14(5-19)17-21-7-11(8-24)26-17/h2-4,6-7,14,22,24H,5,8,19H2,1H3,(H,23,25)/t14-/m1/s1

Standard InChI Key:  LYJLBRBEPGBBQG-CQSZACIVSA-N

Molfile:  

 
     RDKit          2D

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   15.4883   -7.1276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2070   -6.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7976   -7.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4413   -8.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6303   -7.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3151   -5.9306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0737   -5.6221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6467   -5.4626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5992   -7.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0677   -8.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2962   -9.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7297   -9.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9346   -9.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7061   -8.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2726   -8.3258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3721  -10.2904    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.7136   -4.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4518   -4.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0245   -3.3656    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.0412   -4.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2694   -4.4516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7736   -3.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2403   -3.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9738   -2.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1672   -2.2078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5216   -3.4880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  1  5  1  0
  6  7  2  0
  6  8  1  0
  2  6  1  0
  3  9  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 13 16  1  0
  5 10  1  0
 17 18  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 19 23  1  0
 24 25  1  0
 23 24  1  0
 17 20  1  0
 18 26  1  0
 17  8  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4476838

   ---

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: 391.88

Molecular Weight (Monoisotopic): 391.0870

AlogP: 2.42

#Rotatable Bonds: 6

Polar Surface Area: 116.92

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.68

CX Basic pKa: 8.36

CX LogP: 1.14

CX LogD: 0.14

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.51

Np Likeness Score: -0.99

References

1. Curreli F, Ahmed S, Benedict Victor SM, Iusupov IR, Belov DS, Markov PO, Kurkin AV, Altieri A, Debnath AK..  (2020)  Preclinical Optimization of gp120 Entry Antagonists as anti-HIV-1 Agents with Improved Cytotoxicity and ADME Properties through Rational Design, Synthesis, and Antiviral Evaluation.,  63  (4): [PMID:32031803] [10.1021/acs.jmedchem.9b02149]

Source

Source(1):

• Scientific Literature