ID: ALA605866

Max Phase: Preclinical

Molecular Formula: C10H12N6O4

Molecular Weight: 280.24

Molecule Type: Small molecule

Representations

Canonical SMILES:  NC(=O)[C@H]1OC(n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C10H12N6O4/c11-7-3-9(14-1-13-7)16(2-15-3)10-5(18)4(17)6(20-10)8(12)19/h1-2,4-6,10,17-18H,(H2,12,19)(H2,11,13,14)/t4-,5+,6-,10?/m0/s1

Standard InChI Key:  BLMHAOGGJQDPLX-TXDDJGQJSA-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: 280.24

Molecular Weight (Monoisotopic): 280.0920

AlogP: -2.49

#Rotatable Bonds: 2

Polar Surface Area: 162.40

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.40

CX Basic pKa: 4.92

CX LogP: -2.58

CX LogD: -2.58

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.47

Np Likeness Score: 0.88

References

1. Olsson RA, Kusachi S, Thompson RD, Ukena D, Padgett W, Daly JW..  (1986)  N6-substituted N-alkyladenosine-5'-uronamides: bifunctional ligands having recognition groups for A1 and A2 adenosine receptors.,  29  (9): [PMID:3018244] [10.1021/jm00159a020]

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. Matsuda A, Kosaki H, Saitoh Y, Yoshimura Y, Minakawa N, Nakata H..  (1998)  Nucleosides and nucleotides. 177. 9-(6,7-dideoxy-beta-D-allo-hept-5- ynofuranosyl)adenine: a selective and potent ligand for P3 purinoceptor-like protein.,  41  (15): [PMID:9667957] [10.1021/jm9802822]

4. 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]

5. Wnuk SF, Liu S, Yuan CS, Borchardt RT, Robins MJ..  (1996)  Inactivation of S-adenosyl-L-homocysteine hydrolase by amide and ester derivatives of adenosine-5'-carboxylic acid.,  39  (21): [PMID:8863793] [10.1021/jm960313y]

6. Gallo-Rodriguez C, Ji XD, Melman N, Siegman BD, Sanders LH, Orlina J, Fischer B, Pu Q, Olah ME, van Galen PJ..  (1994)  Structure-activity relationships of N6-benzyladenosine-5'-uronamides as A3-selective adenosine agonists.,  37  (5): [PMID:8126704] [10.1021/jm00031a014]

Source

Source(1):

• Scientific Literature