tetrasodium 9-[(3R)-4-[(2S)-2-hydroxy-2-phosphonato-ethoxy]-1-(3-phosphonatopropanoyl)pyrrolidin-3-yl]-1H-purin-6-one

ID: ALA5184028

Chembl Id: CHEMBL5184028

PubChem CID: 168278494

Max Phase: Preclinical

Molecular Formula: C14H17N5Na4O10P2

Molecular Weight: 481.30

Names and Identifiers

Canonical SMILES:  O=C(CCP(=O)([O-])[O-])N1CC(OC[C@@H](O)P(=O)([O-])[O-])[C@H](n2cnc3c(=O)[nH]cnc32)C1.[Na+].[Na+].[Na+].[Na+]

Standard InChI:  InChI=1S/C14H21N5O10P2.4Na/c20-10(1-2-30(23,24)25)18-3-8(9(4-18)29-5-11(21)31(26,27)28)19-7-17-12-13(19)15-6-16-14(12)22;;;;/h6-9,11,21H,1-5H2,(H,15,16,22)(H2,23,24,25)(H2,26,27,28);;;;/q;4*+1/p-4/t8-,9?,11+;;;;/m1..../s1

Standard InChI Key:  GUTAZEVYCQCAIH-GRZPVHHXSA-J

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 481.30

Molecular Weight (Monoisotopic): 481.0764

AlogP: -2.05

#Rotatable Bonds: 8

Polar Surface Area: 228.40

Molecular Species: ACID

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 15

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.15

CX Basic pKa: 0.63

CX LogP: -5.32

CX LogD: -9.69

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.22

Np Likeness Score: -0.02

References

1. Klejch T, Keough DT, King G, Doleželová E, Česnek M, Buděšínský M, Zíková A, Janeba Z, Guddat LW, Hocková D..  (2022)  Stereo-Defined Acyclic Nucleoside Phosphonates are Selective and Potent Inhibitors of Parasite 6-Oxopurine Phosphoribosyltransferases.,  65  (5.0): [PMID:35175749] [10.1021/acs.jmedchem.1c01881]

Source

Source(1):

• Scientific Literature