Phosphoric acid mono-[5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester

ID: ALA603336

Chembl Id: CHEMBL603336

PubChem CID: 24848406

Max Phase: Preclinical

Molecular Formula: C9H13N2O9P

Molecular Weight: 324.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1ccn(C2O[C@H](COP(=O)(O)O)[C@@H](O)[C@@H]2O)c(=O)[nH]1

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

Standard InChI Key:  DJJCXFVJDGTHFX-STUHELBRSA-N

Alternative Forms

1. Parent:

   

   ALA603336

   [(2R,3S,4S)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate

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: 1.23

CX Basic pKa: ┄

CX LogP: -2.54

CX LogD: -6.07

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.37

Np Likeness Score: 1.44

References

1. Nakayama C, Wataya Y, Santi DV, Saneyoshi M, Ueda T..  (1981)  Interaction of 1-(5-phospho-beta-D-arabinofuranosyl)-5-substituted-uracils with thymidylate synthetase: mechanism-based inhibition by 1-(5-phospho-beta-D-arabinosyl)-5-fluorouracil.,  24  (10): [PMID:7328576] [10.1021/jm00142a008]

2. Kim HS, Ravi RG, Marquez VE, Maddileti S, Wihlborg AK, Erlinge D, Malmsjö M, Boyer JL, Harden TK, Jacobson KA..  (2002)  Methanocarba modification of uracil and adenine nucleotides: high potency of Northern ring conformation at P2Y1, P2Y2, P2Y4, and P2Y11 but not P2Y6 receptors.,  45  (1): [PMID:11754592] [10.1021/jm010369e]

3. Pendergast W, Johnson JV, Dickerson SH, Dev IK, Duch DS, Ferone R, Hall WR, Humphreys J, Kelly JM, Wilson DC..  (1993)  Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones.,  36  (16): [PMID:8360872] [10.1021/jm00068a004]

4. Traynor AJ, Hall ET, Walker G, Miller WH, Melançon P, Kuchta RD..  (1996)  Inhibition of UDP-N-acetylglucosamine import into Golgi membranes by nucleoside monophosphates.,  39  (15): [PMID:8709123] [10.1021/jm960175c]

Source

Source(1):

• Scientific Literature