5-(6-Amino-purin-9-yl)-2-hydroxymethyl-3-methyl-tetrahydro-furan-3,4-diol

ID: ALA480143

Chembl Id: CHEMBL480143

Cas Number: 15397-13-4

PubChem CID: 493225

Max Phase: Preclinical

Molecular Formula: C11H15N5O4

Molecular Weight: 281.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3'-C-Methyladenosine | 3'-C-Methyladenosine|15397-13-4|3'-b-C-Methyladenosine|CHEMBL480143|(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol|3'-C-Methyl Ado|SCHEMBL1066935|BDBM50408410|(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-3-methyloxolane-3,4-diol|9-(3'-C-Methyl-.beta.-D-ribofuranosyl) adenine|(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-3-methyloxolane-3,4-diol|(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-3-methyl-teShow More⌵

Canonical SMILES:  C[C@@]1(O)[C@@H](CO)O[C@@H](n2cnc3c(N)ncnc32)[C@@H]1O

Standard InChI:  InChI=1S/C11H15N5O4/c1-11(19)5(2-17)20-10(7(11)18)16-4-15-6-8(12)13-3-14-9(6)16/h3-5,7,10,17-19H,2H2,1H3,(H2,12,13,14)/t5-,7+,10-,11-/m1/s1

Standard InChI Key:  MLIWWOXSMXQECL-ZGUVBZSNSA-N

Alternative Forms

1. Parent:

   

   ALA480143

   3'-C-Methyladenosine

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: 281.27

Molecular Weight (Monoisotopic): 281.1124

AlogP: -1.59

#Rotatable Bonds: 2

Polar Surface Area: 139.54

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.32

CX Basic pKa: 3.94

CX LogP: -1.81

CX LogD: -1.81

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.52

Np Likeness Score: 1.41

References

1. Siddiqi SM, Jacobson KA, Esker JL, Olah ME, Ji XD, Melman N, Tiwari KN, Secrist JA, Schneller SW, Cristalli G..  (1995)  Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors.,  38  (7): [PMID:7707320] [10.1021/jm00007a014]

2. Cappellacci L, Barboni G, Palmieri M, Pasqualini M, Grifantini M, Costa B, Martini C, Franchetti P..  (2002)  Ribose-modified nucleosides as ligands for adenosine receptors: synthesis, conformational analysis, and biological evaluation of 1'-C-methyl adenosine analogues.,  45  (6): [PMID:11881988] [10.1021/jm0102755]

3. Franchetti P, Cappellacci L, Marchetti S, Trincavelli L, Martini C, Mazzoni MR, Lucacchini A, Grifantini M..  (1998)  2'-C-Methyl analogues of selective adenosine receptor agonists: synthesis and binding studies.,  41  (10): [PMID:9572897] [10.1021/jm9707737]

4. Eldrup AB, Allerson CR, Bennett CF, Bera S, Bhat B, Bhat N, Bosserman MR, Brooks J, Burlein C, Carroll SS, Cook PD, Getty KL, MacCoss M, McMasters DR, Olsen DB, Prakash TP, Prhavc M, Song Q, Tomassini JE, Xia J..  (2004)  Structure-activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase.,  47  (9): [PMID:15084127] [10.1021/jm030424e]

5. Franchetti P, Cappellacci L, Pasqualini M, Petrelli R, Vita P, Jayaram HN, Horvath Z, Szekeres T, Grifantini M..  (2005)  Antitumor activity of C-methyl-beta-D-ribofuranosyladenine nucleoside ribonucleotide reductase inhibitors.,  48  (15): [PMID:16033277] [10.1021/jm048944c]

6. Cappellacci L, Franchetti P, Pasqualini M, Petrelli R, Vita P, Lavecchia A, Novellino E, Costa B, Martini C, Klotz KN, Grifantini M..  (2005)  Synthesis, biological evaluation, and molecular modeling of ribose-modified adenosine analogues as adenosine receptor agonists.,  48  (5): [PMID:15743197] [10.1021/jm049408n]

7. Cappellacci L, Franchetti P, Vita P, Petrelli R, Lavecchia A, Jayaram HN, Saiko P, Graser G, Szekeres T, Grifantini M..  (2008)  Ribose-modified purine nucleosides as ribonucleotide reductase inhibitors. Synthesis, antitumor activity, and molecular modeling of N6-substituted 3'-C-methyladenosine derivatives.,  51  (14): [PMID:18588281] [10.1021/jm800205c]

8. Cappellacci L, Petrelli R, Franchetti P, Vita P, Kusumanchi P, Kumar M, Jayaram HN, Zhou B, Yen Y, Grifantini M..  (2011)  Synthesis and biological activity of novel N6-substituted and 2,N6-disubstituted adenine ribo- and 3'-C-methyl-ribonucleosides as antitumor agents.,  46  (5): [PMID:21349610] [10.1016/j.ejmech.2011.01.055]

9. Petrelli R, Meli M, Vita P, Torquati I, Ferro A, Vodnala M, D'Alessandro N, Tolomeo M, Del Bello F, Kusumanchi P, Franchetti P, Grifantini M, Jayaram HN, Hofer A, Cappellacci L..  (2014)  From the covalent linkage of drugs to novel inhibitors of ribonucleotide reductase: synthesis and biological evaluation of valproic esters of 3'-C-methyladenosine.,  24  (22): [PMID:25304896] [10.1016/j.bmcl.2014.09.046]

Source

Source(1):

• Scientific Literature