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

ID: ALA258728

Chembl Id: CHEMBL258728

Cas Number: 84-52-6

PubChem CID: 66535

Max Phase: Preclinical

Molecular Formula: C9H14N3O8P

Molecular Weight: 323.20

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Cytidine 3'-Phosphate | Cytidine 3'-monophosphate|84-52-6|3'-Cytidylic acid|Cytidine-3'-Monophosphate|3'-CMP|3-Cytidylic acid|Cytidine 3'-phosphate|Cytidine 3-monophosphate|Cytidine-3/'-Monophosphate|6DZL5I6D4D|CHEMBL258728|CHEBI:53013|[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] dihydrogen phosphate|(2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl dihydrogen phosphate|C3P|UNII-6DZL5I6D4D|Cytidylic acid B|Show More

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

Alternative Forms

  1. Parent:

Associated Targets(Human)

RNASE1 Tchem Ribonuclease pancreatic (45 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

RNASE1 Ribonuclease pancreatic (177 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SRN Seminal ribonuclease (5 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 323.20Molecular Weight (Monoisotopic): 323.0519AlogP: -2.45#Rotatable Bonds: 4
Polar Surface Area: 177.36Molecular Species: ACIDHBA: 9HBD: 5
#RO5 Violations: HBA (Lipinski): 11HBD (Lipinski): 6#RO5 Violations (Lipinski): 2
CX Acidic pKa: 0.87CX Basic pKa: CX LogP: -2.92CX LogD: -6.75
Aromatic Rings: 1Heavy Atoms: 21QED Weighted: 0.37Np 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,