ID: ALA2070507

Max Phase: Preclinical

Molecular Formula: C14H18N6O4

Molecular Weight: 334.34

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](C(=O)NC2CCC2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C14H18N6O4/c15-11-7-12(17-4-16-11)20(5-18-7)14-9(22)8(21)10(24-14)13(23)19-6-2-1-3-6/h4-6,8-10,14,21-22H,1-3H2,(H,19,23)(H2,15,16,17)/t8-,9+,10-,14+/m0/s1

Standard InChI Key:  CGYRWWMWNACLSU-AEISUSGSSA-N

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

Properties

Molecular Weight: 334.34

Molecular Weight (Monoisotopic): 334.1390

AlogP: -1.30

#Rotatable Bonds: 3

Polar Surface Area: 148.41

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.39

CX Basic pKa: 4.92

CX LogP: -1.44

CX LogD: -1.44

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.54

Np Likeness Score: 0.44

References

1. de Zwart M, Kourounakis A, Kooijman H, Spek AL, Link R, von Frijtag Drabbe Künzel JK, IJzerman AP..  (1999)  5'-N-substituted carboxamidoadenosines as agonists for adenosine receptors.,  42  (8): [PMID:10212124] [10.1021/jm9804984]

2. Umino T, Yoshioka K, Saitoh Y, Minakawa N, Nakata H, Matsuda A..  (2001)  Nucleosides and nucleotides. 200. Reinvestigation of 5'-N-ethylcarboxamidoadenosine derivatives: structure-activity relationships for P(3) purinoceptor-like proteins.,  44  (2): [PMID:11170630] [10.1021/jm000150k]

3. Prasad RN, Bariana DS, Fung A, Savic M, Tietje K, Stein HH, Brondyk H, Egan RS..  (1980)  Modification of the 5' position of purine nucleosides. 2. Synthesis and some cardiovascular properties of adenosine-5'-(N-substituted)carboxamides.,  23  (3): [PMID:7365748] [10.1021/jm00177a021]

4. Tosh DK, Phan K, Gao ZG, Gakh AA, Xu F, Deflorian F, Abagyan R, Stevens RC, Jacobson KA, Katritch V..  (2012)  Optimization of adenosine 5'-carboxamide derivatives as adenosine receptor agonists using structure-based ligand design and fragment screening.,  55  (9): [PMID:22486652] [10.1021/jm300095s]

5. Ghosh A, Dimova D, Bajorath J.  (2016)  Classification of matching molecular series on the basis of SAR phenotypes and structural relationships,  7  (2): [10.1039/C5MD00566C]

6. Tosh DK,Brackett CM,Jung YH,Gao ZG,Banerjee M,Blagg BSJ,Jacobson KA.  (2021)  Biological Evaluation of 5'-(N-Ethylcarboxamido)adenosine Analogues as Grp94-Selective Inhibitors.,  12  (3): [PMID:33738064] [10.1021/acsmedchemlett.0c00509]

Source

Source(1):

• Scientific Literature