[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl][(2S,3R,4S,5S)-3,4,5-trihydroxytetrahydrofuran-2-yl]methyl hydrogen phosphate

ID: ALA4226903

Chembl Id: CHEMBL4226903

PubChem CID: 10437766

Max Phase: Preclinical

Molecular Formula: C15H23N5O14P2

Molecular Weight: 559.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OC[C@@H]2O[C@H](O)[C@@H](O)[C@H]2O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H23N5O14P2/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(23)8(21)5(32-14)1-30-35(26,27)34-36(28,29)31-2-6-9(22)11(24)15(25)33-6/h3-6,8-11,14-15,21-25H,1-2H2,(H,26,27)(H,28,29)(H2,16,17,18)/t5-,6+,8-,9+,10-,11+,14-,15+/m1/s1

Standard InChI Key:  SRNWOUGRCWSEMX-ZIXUEBECSA-N

Alternative Forms

1. Parent:

   

   ALA4226903

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

Molecule Features

Natural Product: Yes

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: 559.32

Molecular Weight (Monoisotopic): 559.0717

AlogP: -3.28

#Rotatable Bonds: 9

Polar Surface Area: 291.52

Molecular Species: ACID

HBA: 17

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 19

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.86

CX Basic pKa: 4.92

CX LogP: -6.16

CX LogD: -8.79

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.14

Np Likeness Score: 1.27

References

1. Zhang Y, Jumppanen M, Maksimainen MM, Auno S, Awol Z, Ghemtio L, Venkannagari H, Lehtiö L, Yli-Kauhaluoma J, Xhaard H, Boije Af Gennäs G..  (2018)  Adenosine analogs bearing phosphate isosteres as human MDO1 ligands.,  26  (8): [PMID:29501416] [10.1016/j.bmc.2018.02.006]

2. Fiorentino F, Mai A, Rotili D..  (2021)  Emerging Therapeutic Potential of SIRT6 Modulators.,  64  (14.0): [PMID:34213345] [10.1021/acs.jmedchem.1c00601]

Source

Source(1):

• Scientific Literature