Acetic acid 4-acetoxy-5-acetoxymethyl-2-[4-(3-phenyl-allylsulfanyl)-pyrazolo[3,4-d]pyrimidin-1-yl]-tetrahydro-furan-3-yl ester

ID: ALA3143939

PubChem CID: 70539003

Max Phase: Preclinical

Molecular Formula: C25H26N4O7S

Molecular Weight: 526.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](n2ncc3c(SC/C=C/c4ccccc4)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C25H26N4O7S/c1-15(30)33-13-20-21(34-16(2)31)22(35-17(3)32)25(36-20)29-23-19(12-28-29)24(27-14-26-23)37-11-7-10-18-8-5-4-6-9-18/h4-10,12,14,20-22,25H,11,13H2,1-3H3/b10-7+/t20-,21-,22-,25-/m1/s1

Standard InChI Key:  WRVKLPRKUAMVFJ-VMKZXWPISA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3143939

   [(2R,3R,4R,5R)-3,4-diacetyloxy-5-[4-[(E)-3-phenylprop-2-enyl]sulfanylpyrazolo[3,4-d]pyrimidin-1-yl]oxolan-2-yl]methyl acetate

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: 526.57

Molecular Weight (Monoisotopic): 526.1522

AlogP: 2.96

#Rotatable Bonds: 9

Polar Surface Area: 131.73

Molecular Species: NEUTRAL

HBA: 12

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 2.14

CX LogP: 2.86

CX LogD: 2.86

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.18

Np Likeness Score: 0.06

References

1. Rideout JL, Krenitsky TA, Chao EY, Elion GB, Williams RB, Latter VS..  (1983)  Pyrazolo[3,4-d]pyrimidine ribonucleosides as anticoccidials. 3. Synthesis and activity of some nucleosides of 4-[(arylalkenyl)thio]pyrazolo[3,4-d]pyrimidines.,  26  (10): [PMID:6620308] [10.1021/jm00364a024]

Source

Source(1):

• Scientific Literature