3-(3',5'-di-O-acetyl-2'-deoxy-beta-D-ribofuranosyl)-5-(3-hydroxyprop-1-yn-1-yl)-6-(4-methylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one

ID: ALA4777798

PubChem CID: 162643964

Max Phase: Preclinical

Molecular Formula: C25H24N2O8

Molecular Weight: 480.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](n2cc3c(C#CCO)c(-c4ccc(C)cc4)oc3nc2=O)C[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C25H24N2O8/c1-14-6-8-17(9-7-14)23-18(5-4-10-28)19-12-27(25(31)26-24(19)35-23)22-11-20(33-16(3)30)21(34-22)13-32-15(2)29/h6-9,12,20-22,28H,10-11,13H2,1-3H3/t20-,21+,22+/m0/s1

Standard InChI Key:  ZWZNTCNJBPVUMU-BHDDXSALSA-N

Molfile:  

 
     RDKit          2D

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    6.3850   -4.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2333   -2.4403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5593   -2.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1742   -3.6213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5548   -4.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5173   -3.1906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7170   -3.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8 10  1  0
  4 16  2  0
 17 18  3  0
  7 17  1  0
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 19 20  1  0
 13 21  1  0
 22 23  1  0
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 24 25  1  0
 25 26  1  0
 26 22  1  0
 24  1  1  1
 26 27  1  1
 27 28  1  0
 28 29  1  0
 29 30  1  0
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 22 32  1  6
 32 33  1  0
 33 34  1  0
 33 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4777798

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 480.47

Molecular Weight (Monoisotopic): 480.1533

AlogP: 2.09

#Rotatable Bonds: 5

Polar Surface Area: 130.09

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.28

CX Basic pKa: ┄

CX LogP: 1.17

CX LogD: 1.17

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.43

Np Likeness Score: 0.72

References

1. Kaczmarek R,Twardy DJ,Olson TL,Korczyński D,Andrei G,Snoeck R,Dolot R,Wheeler KA,Dembinski R.  (2021)  Extension of furopyrimidine nucleosides with 5-alkynyl substituent: Synthesis, high fluorescence, and antiviral effect in the absence of free ribose hydroxyl groups.,  209  [PMID:33039724] [10.1016/j.ejmech.2020.112884]

Source

Source(1):

• Scientific Literature