(Sp)-3'-Deoxyadenosine 5'-O-phenyl-(benzoxy-L-alaninyl)phosphate

ID: ALA5269483

Chembl Id: CHEMBL5269483

Max Phase: Preclinical

Molecular Formula: C26H29N6O7P

Molecular Weight: 568.53

Names and Identifiers

Canonical SMILES:  C[C@H](N[P@](=O)(OC[C@@H]1C[C@@H](O)[C@H](n2cnc3c(N)ncnc32)O1)Oc1ccccc1)C(=O)OCc1ccccc1

Standard InChI:  InChI=1S/C26H29N6O7P/c1-17(26(34)36-13-18-8-4-2-5-9-18)31-40(35,39-19-10-6-3-7-11-19)37-14-20-12-21(33)25(38-20)32-16-30-22-23(27)28-15-29-24(22)32/h2-11,15-17,20-21,25,33H,12-14H2,1H3,(H,31,35)(H2,27,28,29)/t17-,20-,21+,25+,40-/m0/s1

Standard InChI Key:  UDLWWGQHMQIYCV-GNIJUVTDSA-N

Alternative Forms

1. Parent:

   

   ALA5269483

   ---

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: 568.53

Molecular Weight (Monoisotopic): 568.1835

AlogP: 2.98

#Rotatable Bonds: 11

Polar Surface Area: 172.94

Molecular Species: NEUTRAL

HBA: 12

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.24

CX Basic pKa: 3.94

CX LogP: 2.08

CX LogD: 2.08

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.18

Np Likeness Score: 0.40

References

1. Serpi M, Ferrari V, McGuigan C, Ghazaly E, Pepper C..  (2022)  Synthesis and Characterization of NUC-7738, an Aryloxy Phosphoramidate of 3'-Deoxyadenosine, as a Potential Anticancer Agent.,  65  (23.0): [PMID:36417756] [10.1021/acs.jmedchem.2c01348]

Source

Source(1):

• Scientific Literature