4-Amino-1-(4,5-dihydroxy-3-hydroxymethyl-cyclopent-2-enyl)-1H-pyrimidin-2-one

ID: ALA63647

Chembl Id: CHEMBL63647

Cas Number: 90597-22-1

PubChem CID: 72828

Max Phase: Preclinical

Molecular Formula: C10H13N3O4

Molecular Weight: 239.23

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H13N3O4/c11-7-1-2-13(10(17)12-7)6-3-5(4-14)8(15)9(6)16/h1-3,6,8-9,14-16H,4H2,(H2,11,12,17)/t6-,8-,9+/m1/s1

Standard InChI Key:  DUJGMZAICVPCBJ-VDAHYXPESA-N

Alternative Forms

1. Parent:

   

   ALA63647

   Cyclopentenyl cytosine

Molecule Features

Natural Product: No

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: 239.23

Molecular Weight (Monoisotopic): 239.0906

AlogP: -1.98

#Rotatable Bonds: 2

Polar Surface Area: 121.60

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.16

CX Basic pKa: ┄

CX LogP: -2.90

CX LogD: -2.90

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.44

Np Likeness Score: 1.38

References

1. Chu CK, Jin YH, Baker RO, Huggins J..  (2003)  Antiviral activity of cyclopentenyl nucleosides against orthopox viruses (Smallpox, monkeypox and cowpox).,  13  (1): [PMID:12467606] [10.1016/s0960-894x(02)00841-7]

2. Lim MI, Moyer JD, Cysyk RI, Marquez VE..  (1984)  Cyclopentenyluridine and cyclopentenylcytidine analogues as inhibitors of uridine-cytidine kinase.,  27  (12): [PMID:6094806] [10.1021/jm00378a002]

3. Marquez VE, Lim MI, Treanor SP, Plowman J, Priest MA, Markovac A, Khan MS, Kaskar B, Driscoll JS..  (1988)  Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties.,  31  (9): [PMID:3411597] [10.1021/jm00117a004]

4. Copp RR, Marquez VE..  (1991)  Synthesis of two cyclopentenyl-3-deazapyrimidine carbocyclic nucleosides related to cytidine and uridine.,  34  (1): [PMID:1992119] [10.1021/jm00105a032]

5. Song GY, Paul V, Choo H, Morrey J, Sidwell RW, Schinazi RF, Chu CK..  (2001)  Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus.,  44  (23): [PMID:11689085] [10.1021/jm010256v]

6. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays