(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl dihydrogen phosphate

ID: ALA460741

Chembl Id: CHEMBL460741

Cas Number: 35170-03-7

PubChem CID: 101543

Max Phase: Preclinical

Molecular Formula: C9H13N2O9P

Molecular Weight: 324.18

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Uridine 3'-Phosphate | 3'-Uridylic acid|Uridine 3'-phosphate|3'-UMP|3'-URIDINEMONOPHOSPHATE|Uridine 3'-monophosphate|ZI74VYB8VZ|CHEMBL460741|[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] dihydrogen phosphate|CHEBI:28895|35170-03-7|U3P|Uracylsaure|4rsk|3''-uridylic acid|uridine-3'-phosphate|1o0n|UNII-ZI74VYB8VZ|3-UMPNA|SCHEMBL345577|3''-UMP|DTXSID401018973|Uridine 3'-(dihydrogen phosphate)|EINECS 201-538-0|BDBM50292722|DB02714|PD042601|NS00069767|C01368|Q27103Show More⌵

Canonical SMILES:  O=c1ccn([C@@H]2O[C@H](CO)[C@@H](OP(=O)(O)O)[C@H]2O)c(=O)[nH]1

Standard InChI:  InChI=1S/C9H13N2O9P/c12-3-4-7(20-21(16,17)18)6(14)8(19-4)11-2-1-5(13)10-9(11)15/h1-2,4,6-8,12,14H,3H2,(H,10,13,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1

Standard InChI Key:  FOGRQMPFHUHIGU-XVFCMESISA-N

Alternative Forms

1. Parent:

   

   ALA460741

   3'-Uridylic acid

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: 324.18

Molecular Weight (Monoisotopic): 324.0359

AlogP: -2.73

#Rotatable Bonds: 4

Polar Surface Area: 171.31

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.87

CX Basic pKa: ┄

CX LogP: -2.54

CX LogD: -6.37

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.37

Np Likeness Score: 1.47

References

1. 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]

2. 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]

Source

Source(1):

• Scientific Literature