4-Amino-1-(4-hydroxy-5-hydroxymethyl-3-methylene-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one

ID: ALA10128

Chembl Id: CHEMBL10128

PubChem CID: 44266514

Max Phase: Preclinical

Molecular Formula: C10H13N3O4

Molecular Weight: 239.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(n2ccc(N)nc2=O)O[C@H](CO)[C@@H]1O

Standard InChI:  InChI=1S/C10H13N3O4/c1-5-8(15)6(4-14)17-9(5)13-3-2-7(11)12-10(13)16/h2-3,6,8-9,14-15H,1,4H2,(H2,11,12,16)/t6-,8-,9?/m1/s1

Standard InChI Key:  PULHLIOPJXPGJN-GLXOAHRXSA-N

Alternative Forms

1. Parent:

   

   ALA10128

   4-amino-1-[(4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylideneoxolan-2-yl]pyrimidin-2-one

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: -1.37

#Rotatable Bonds: 2

Polar Surface Area: 110.60

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.41

CX Basic pKa: ┄

CX LogP: -1.78

CX LogD: -1.78

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.55

Np Likeness Score: 1.34

References

1. Takenuki K, Matsuda A, Ueda T, Sasaki T, Fujii A, Yamagami K..  (1988)  Design, synthesis, and antineoplastic activity of 2'-deoxy-2'-methylidenecytidine.,  31  (6): [PMID:3373480] [10.1021/jm00401a001]

2. Shuto S, Awano H, Fujii A, Yamagami K, Matsuda A.  (1996)  Nucleosides and nucleotides. 155. synthesis, antitumor effects, and possible enzymatic activation mechanism of 5-phosphatidyl-2-deoxy-2-methylenecytidine (DMDC),  6  (18): [10.1016/0960-894X(96)00389-7]

3. Robins MJ, Samano V, Zhang W, Balzarini J, De Clercq E, Borchardt RT, Lee Y, Yuan CS..  (1992)  Nucleic acid related compounds. 74. Synthesis and biological activity of 2'(and 3')-deoxy-2'(and 3')-methylenenucleoside analogues that function as mechanism-based inhibitors of S-adenosyl-L-homocysteine hydrolase and/or ribonucleotide reductase.,  35  (12): [PMID:1613752] [10.1021/jm00090a020]

4. Lin TS, Luo MZ, Liu MC, Clarke-Katzenburg RH, Cheng YC, Prusoff WH, Mancini WR, Birnbaum GI, Gabe EJ, Giziewicz J..  (1991)  Synthesis and anticancer and antiviral activities of various 2'- and 3'-methylidene-substituted nucleoside analogues and crystal structure of 2'-deoxy-2'-methylidenecytidine hydrochloride.,  34  (8): [PMID:1652024] [10.1021/jm00112a040]

5. Matsuda A, Takenuki K, Tanaka M, Sasaki T, Ueda T..  (1991)  Nucleosides and nucleotides. 97. Synthesis of new broad spectrum antineoplastic nucleosides, 2'-deoxy-2'-methylidenecytidine (DMDC) and its derivatives.,  34  (2): [PMID:1995905] [10.1021/jm00106a049]

Source

Source(1):

• Scientific Literature