ID: ALA258728

Max Phase: Preclinical

Molecular Formula: C9H14N3O8P

Molecular Weight: 323.20

Molecule Type: Small molecule

Representations

Synonyms (1): Cytidine 3'-Phosphate
Synonyms from Alternative Forms(1):

Canonical SMILES:  Nc1ccn([C@@H]2O[C@H](CO)[C@@H](OP(=O)(O)O)[C@H]2O)c(=O)n1

Standard InChI:  InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-6(14)7(4(3-13)19-8)20-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1

Standard InChI Key:  UOOOPKANIPLQPU-XVFCMESISA-N

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

Properties

Molecular Weight: 323.20

Molecular Weight (Monoisotopic): 323.0519

AlogP: -2.45

#Rotatable Bonds: 4

Polar Surface Area: 177.36

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.87

CX Basic pKa:

CX LogP: -2.92

CX LogD: -6.75

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.37

Np Likeness Score: 1.60

References

1. Ghosh KS, Debnath J, Dutta P, Sahoo BK, Dasgupta S..  (2008)  Exploring the potential of 3'-O-carboxy esters of thymidine as inhibitors of ribonuclease A and angiogenin.,  16  (6): [PMID:18226913] [10.1016/j.bmc.2008.01.003]

2. Samanta A, Leonidas DD, Dasgupta S, Pathak T, Zographos SE, Oikonomakos NG..  (2009)  Morpholino, piperidino, and pyrrolidino derivatives of pyrimidine nucleosides as inhibitors of ribonuclease A: synthesis, biochemical, and crystallographic evaluation.,  52  (4): [PMID:19173562] [10.1021/jm800724t]

3. Debnath J, Dasgupta S, Pathak T..  (2009)  Nucleoside-amino acid conjugates: An alternative route to the design of ribonuclease A inhibitors.,  17  (14): [PMID:19540766] [10.1016/j.bmc.2009.06.002]

4. Dossi K, Tsirkone VG, Hayes JM, Matousek J, Poucková P, Soucek J, Zadinova M, Zographos SE, Leonidas DD..  (2009)  Mapping the ribonucleolytic active site of bovine seminal ribonuclease. The binding of pyrimidinyl phosphonucleotide inhibitors.,  44  (11): [PMID:19643512] [10.1016/j.ejmech.2009.06.039]

5. Dutta S, Basak A, Dasgupta S..  (2010)  Synthesis and ribonuclease A inhibition activity of resorcinol and phloroglucinol derivatives of catechin and epicatechin: Importance of hydroxyl groups.,  18  (17): [PMID:20692173] [10.1016/j.bmc.2010.06.077]

6. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays