p5'A2'p5'A2'p5'A2'p5'A

ID: ALA601940

Chembl Id: CHEMBL601940

PubChem CID: 11686847

Max Phase: Preclinical

Molecular Formula: C40H50N20O25P4

Molecular Weight: 1334.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O[C@@H]2[C@H](O)[C@@H](COP(=O)(O)O[C@@H]3[C@H](O)[C@@H](COP(=O)(O)O[C@@H]4[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]4n4cnc5c(N)ncnc54)O[C@H]3n3cnc4c(N)ncnc43)O[C@H]2n2cnc3c(N)ncnc32)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C40H50N20O25P4/c41-29-17-33(49-5-45-29)57(9-53-17)37-25(65)21(61)13(79-37)2-76-87(69,70)84-27-23(63)15(81-39(27)59-11-55-19-31(43)47-7-51-35(19)59)4-78-89(73,74)85-28-24(64)16(82-40(28)60-12-56-20-32(44)48-8-52-36(20)60)3-77-88(71,72)83-26-22(62)14(1-75-86(66,67)68)80-38(26)58-10-54-18-30(42)46-6-50-34(18)58/h5-16,21-28,37-40,61-65H,1-4H2,(H,69,70)(H,71,72)(H,73,74)(H2,41,45,49)(H2,42,46,50)(H2,43,47,51)(H2,44,48,52)(H2,66,67,68)/t13-,14-,15-,16-,21-,22-,23-,24-,25-,26-,27-,28-,37-,38-,39-,40-/m1/s1

Standard InChI Key:  COOGAGWMNGSZRA-HKIDEBSPSA-N

Alternative Forms

1. Parent:

   

   ALA601940

   [(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-3-hydroxyoxolan-2-yl]methyl [(2R

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: 1334.85

Molecular Weight (Monoisotopic): 1334.2206

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References

1. Torrence PF, Imai J, Lesiak K, Jamoulle JC, Sawai H..  (1984)  Oligonucleotide structural parameters that influence binding of 5'-O-triphosphoadenylyl-(2'----5')-adenylyl-(2'----5')-adenosine to the 5'-O-triphosphoadenylyl-(2'----5')-adenylyl-(2'----5')-adenosine dependent endoribonuclease: chain length, phosphorylation state, and heterocyclic base.,  27  (6): [PMID:6737414] [10.1021/jm00372a004]

2. Ueno Y, Ishihara S, Ito Y, Kitade Y..  (2004)  Synthesis of 2',5'-oligoadenylate analogs containing an adenine acyclonucleoside and their ability to activate human RNase L.,  14  (17): [PMID:15357966] [10.1016/j.bmcl.2004.06.071]

3. Nagaoka K, Kitamura Y, Ueno Y, Kitade Y..  (2010)  5'-O-dephosphorylated 2',5'-oligoadenylate (2-5A) with 8-methyladenosine at the 2'-terminus activates human RNase L.,  20  (3): [PMID:20022497] [10.1016/j.bmcl.2009.12.005]

4. Páv O, Panova N, Snášel J, Zborníková E, Rosenberg I..  (2012)  Activation of human RNase L by 2'- and 5'-O-methylphosphonate-modified oligoadenylates.,  22  (1): [PMID:22169265] [10.1016/j.bmcl.2011.11.040]

5. Kitamura Y, Kito S, Nakashima R, Tanaka K, Nagaoka K, Kitade Y..  (2016)  Doxifluridine-conjugated 2-5A analog shows strong RNase L activation ability and tumor suppressive effect.,  24  (16): [PMID:27364610] [10.1016/j.bmc.2016.06.033]

Source

Source(1):

• Scientific Literature