((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphoramidate

ID: ALA583986

Chembl Id: CHEMBL583986

Cas Number: 6154-31-0

PubChem CID: 440142

Max Phase: Preclinical

Molecular Formula: C10H15N6O6P

Molecular Weight: 346.24

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H15N6O6P/c11-8-5-9(14-2-13-8)16(3-15-5)10-7(18)6(17)4(22-10)1-21-23(12,19)20/h2-4,6-7,10,17-18H,1H2,(H2,11,13,14)(H3,12,19,20)/t4-,6-,7-,10-/m1/s1

Standard InChI Key:  LDEMREUBLBGZBO-KQYNXXCUSA-N

Alternative Forms

1. Parent:

   

   ALA583986

   Adenosine 5'-phosphoramidate

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: 346.24

Molecular Weight (Monoisotopic): 346.0791

AlogP: -1.90

#Rotatable Bonds: 4

Polar Surface Area: 191.86

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.67

CX Basic pKa: 4.92

CX LogP: -4.22

CX LogD: -5.16

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.39

Np Likeness Score: 1.11

References

1. Hong JA, Bhave DP, Carroll KS..  (2009)  Identification of critical ligand binding determinants in Mycobacterium tuberculosis adenosine-5'-phosphosulfate reductase.,  52  (17): [PMID:19678707] [10.1021/jm900728u]

2. Murakami E, Bao H, Mosley RT, Du J, Sofia MJ, Furman PA..  (2011)  Adenosine deaminase-like protein 1 (ADAL1): characterization and substrate specificity in the hydrolysis of N(6)- or O(6)-substituted purine or 2-aminopurine nucleoside monophosphates.,  54  (16): [PMID:21755941] [10.1021/jm200650j]

3. Baraniak J, Pietkiewicz A, Kaczmarek R, Radzikowska E, Kulik K, Krolewska K, Cieslak M, Krakowiak A, Nawrot B..  (2014)  N-Acyl-phosphoramidates as potential novel form of gemcitabine prodrugs.,  22  (7): [PMID:24631359] [10.1016/j.bmc.2014.02.034]

4. 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