(2S,3R,5R)-2-(2,4-Difluoro-phenylsulfanylmethyl)-5-{6-[(R)-(tetrahydro-furan-3-yl)amino]-purin-9-yl}-tetrahydro-furan-3,4-diol

ID: ALA2092779

PubChem CID: 59991900

Max Phase: Preclinical

Molecular Formula: C20H21F2N5O4S

Molecular Weight: 465.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O[C@@H]1[C@H](O)[C@@H](CSc2ccc(F)cc2F)O[C@H]1n1cnc2c(NC3CCOC3)ncnc21

Standard InChI:  InChI=1S/C20H21F2N5O4S/c21-10-1-2-14(12(22)5-10)32-7-13-16(28)17(29)20(31-13)27-9-25-15-18(23-8-24-19(15)27)26-11-3-4-30-6-11/h1-2,5,8-9,11,13,16-17,20,28-29H,3-4,6-7H2,(H,23,24,26)/t11?,13-,16-,17-,20-/m1/s1

Standard InChI Key:  GJLUJCRJDFVKER-OFGIKRIPSA-N

Molfile:  

     RDKit          2D

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    5.4699   -2.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3018   -1.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3060   -0.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5281   -0.6531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8210   -2.2961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0256   -0.5116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1430   -2.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0131   -2.1588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7369   -0.9276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0298    0.3120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253   -0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7286   -1.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2320   -1.6514    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6322   -4.2595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0514    0.9858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8261   -1.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9152   -0.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8435   -4.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9575   -0.0292    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.7494    0.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607   -1.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1415   -0.5158    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.8367    1.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6396    1.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4981    0.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  1  1  0
  4  3  2  0
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  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  4  1  0
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 15 19  2  0
 16 12  2  0
 17 20  1  0
 18 15  1  0
 19 17  1  0
 11 20  1  1
  6 21  1  6
 22 32  1  0
 23 19  1  0
 24 28  1  0
 10 25  1  6
 26 15  1  0
 27 14  1  0
 28 23  2  0
 29 24  1  0
 30 27  1  0
 31 30  1  0
 32 27  1  0
  5  4  1  0
 10 11  1  0
  9 13  2  0
 31 22  1  0
 24 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2092779

   (2S,3S,4R,5R)-2-[(2,4-difluorophenyl)sulfanylmethyl]-5-[6-(oxolan-3-ylamino)purin-9-yl]oxolane-3,4-diol

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: 465.48

Molecular Weight (Monoisotopic): 465.1282

AlogP: 1.72

#Rotatable Bonds: 6

Polar Surface Area: 114.55

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.47

CX Basic pKa: 3.71

CX LogP: 1.26

CX LogD: 1.26

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.47

Np Likeness Score: -0.25

References

1. Morrison CF, Elzein E, Jiang B, Ibrahim PN, Marquart T, Palle V, Shenk KD, Varkhedkar V, Maa T, Wu L, Wu Y, Zeng D, Fong I, Lustig D, Leung K, Zablocki JA..  (2004)  Structure-affinity relationships of 5'-aromatic ethers and 5'-aromatic sulfides as partial A1 adenosine agonists, potential supraventricular anti-arrhythmic agents.,  14  (14): [PMID:15203164] [10.1016/j.bmcl.2004.04.096]

2. Morrison CF, Elzein E, Jiang B, Ibrahim PN, Marquart T, Palle V, Shenk KD, Varkhedkar V, Maa T, Wu L, Wu Y, Zeng D, Fong I, Lustig D, Leung K, Zablocki JA..  (2004)  Structure-affinity relationships of 5'-aromatic ethers and 5'-aromatic sulfides as partial A1 adenosine agonists, potential supraventricular anti-arrhythmic agents.,  14  (14): [PMID:15203164] [10.1016/j.bmcl.2004.04.096]

Source

Source(1):

• Scientific Literature