(R)-N-(2-amino-1-(5-(hydroxymethyl)thiazol-2-yl)ethyl)-5-(4-(trifluoromethyl)phenyl)-1H-pyrrole-2-carboxamide

ID: ALA4547005

Chembl Id: CHEMBL4547005

PubChem CID: 155552430

Max Phase: Preclinical

Molecular Formula: C18H17F3N4O2S

Molecular Weight: 410.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NC[C@@H](NC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)[nH]1)c1ncc(CO)s1

Standard InChI:  InChI=1S/C18H17F3N4O2S/c19-18(20,21)11-3-1-10(2-4-11)13-5-6-14(24-13)16(27)25-15(7-22)17-23-8-12(9-26)28-17/h1-6,8,15,24,26H,7,9,22H2,(H,25,27)/t15-/m1/s1

Standard InChI Key:  DZYJFGXCMUYKRB-OAHLLOKOSA-N

Alternative Forms

1. Parent:

   

   ALA4547005

   ---

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: 410.42

Molecular Weight (Monoisotopic): 410.1024

AlogP: 3.08

#Rotatable Bonds: 6

Polar Surface Area: 104.03

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.67

CX Basic pKa: 8.36

CX LogP: 1.73

CX LogD: 0.73

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.50

Np Likeness Score: -0.91

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]

2. Curreli F,Belov DS,Kwon YD,Ramesh R,Furimsky AM,O'Loughlin K,Byrge PC,Iyer LV,Mirsalis JC,Kurkin AV,Altieri A,Debnath AK.  (2018)  Structure-based lead optimization to improve antiviral potency and ADMET properties of phenyl-1H-pyrrole-carboxamide entry inhibitors targeted to HIV-1 gp120.,  154  [PMID:29860061] [10.1016/j.ejmech.2018.04.062]

3. Curreli F, Ahmed S, Benedict Victor SM, Iusupov IR, Spiridonov EA, Belov DS, Altieri A, Kurkin AV, Debnath AK..  (2021)  Design, synthesis, and antiviral activity of a series of CD4-mimetic small-molecule HIV-1 entry inhibitors.,  32  [PMID:33461144] [10.1016/j.bmc.2021.116000]

Source

Source(1):

• Scientific Literature