1-(beta-D-2-Deoxyribofuranosyl)-4-hydroxyamino-5-chloropyrimidin-2(1H)-one 5'-monophosphate

ID: ALA1161232

PubChem CID: 10618341

Max Phase: Preclinical

Molecular Formula: C9H13ClN3O8P

Molecular Weight: 357.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1nc(NO)c(Cl)cn1[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1

Standard InChI:  InChI=1S/C9H13ClN3O8P/c10-4-2-13(9(15)11-8(4)12-16)7-1-5(14)6(21-7)3-20-22(17,18)19/h2,5-7,14,16H,1,3H2,(H,11,12,15)(H2,17,18,19)/t5-,6+,7+/m0/s1

Standard InChI Key:  LPQTXABYZTYBDH-RRKCRQDMSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    2.1792   -6.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6667   -6.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -6.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542   -6.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -5.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -5.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -5.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3708   -6.3250    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -6.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -7.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292   -6.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -7.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -5.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1708   -6.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875   -7.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -6.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833   -6.9250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708   -6.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833   -5.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -5.1792    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.3042   -5.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1958   -7.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  1  1
  5  6  1  0
  6  7  2  0
  7  1  1  0
  8 16  1  0
  9  4  1  0
 10  4  1  0
 11  9  1  0
 12 10  1  0
 13  5  1  0
 11 14  1  1
 15  2  2  0
 16 14  1  0
 17  8  1  0
 18  8  1  0
 19  8  2  0
 20  6  1  0
 21 13  1  0
 12 22  1  6
  3  5  2  0
 11 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1161232

   [(2R,3S,5R)-5-[5-chloro-4-(hydroxyamino)-2-oxopyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate

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: 357.64

Molecular Weight (Monoisotopic): 357.0129

AlogP: -0.54

#Rotatable Bonds: 5

Polar Surface Area: 163.37

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.23

CX Basic pKa: ┄

CX LogP: -1.30

CX LogD: -4.82

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.34

Np Likeness Score: 0.78

References

1. Felczak K, Miazga A, Poznański J, Bretner M, Kulikowski T, Dzik JM, Gołos B, Zieliński Z, Cieśla J, Rode W..  (2000)  5-Substituted N(4)-hydroxy-2'-deoxycytidines and their 5'-monophosphates: synthesis, conformation, interaction with tumor thymidylate synthase, and in vitro antitumor activity.,  43  (24): [PMID:11101356] [10.1021/jm000975u]

Source

Source(1):

• Scientific Literature